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37: From Design Leadership to Product Leadership (ft. Che Douglas) Mar 20, 2023

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Transcript Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, And we’re finding our way Peter: navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show, Booking.com’s VP of Product and former VP of Design Che Douglas joins us to talk about the cultural and functional relationship between product and design, what it’s like to lead both as an integrated team, and the necessity of driving alignment in order to drive change as a leader. Peter: Well, hi, Che. Thank you for joining us today. Jesse and I have been talking to a bunch of design leaders over the last well, five or six months, and so we’re excited to have you join us. In particular, we’re excited to have you join because, at least looking at your LinkedIn profile, you’re not simply a design leader. And so I’d love to learn just, like, what your role is, what you do, and how did you end up there? From VP Design to VP Product Che: Great question. So right now I’m working with Booking.com as their Vice President of Product. I joined Booking in end of late 2019 just before the pandemic started. Good time to join a travel company, during a pandemic. Um, I joined as their first Vice President of Design. They’d had kind of director-level designers previously, but no one at the executive level overseeing the community. And with about 300 designers across the organization at the time, they were very interested in bringing someone in that could kind of make sense of all of that and define a strategy globally for the company and set a vision and help point everyone in the right direction. So I came in as a VP of Design. My role transitioned through the pandemic into also running product development. Whole host of reasons for that. I had previously led part of products with The Wall Street Journal towards the end of my role there in New York. So I had experience, and then previous to the Wall Street Journal, I ran a business in Australia doing brand and digital work for about 10 years. So I think my experience of building products, you know, physical and digital environments, branding, all of those things combined, and running the company that I’d started, I think gave me a fairly good grounding to move into what we call product development or software development these days. So, you know, the people that I employed in my business before I joined The Wall Street Journal came from all sorts of disciplines. And, and that’s kind of how you needed to make up a company to do any kind of digital product development or branding work. So, that experience kept following me through my career when I moved to New York, work for The Wall Street Journal and also into the role with Booking as a first Vice President of Design. And, and that evolved quite quickly into, like I said, running product and, and parts of it anyway. The time I joined there was a Chief Product Officer. He was my boss. And he was running basically the program to start building what we call the connected trip, which has been there since even before I joined. So we were still three years into that mission, recently bringing in all of the other things that Booking Holdings has. So supply of flights, everything outside of hotels, so you know, ground transportation, insurance, attractions, you name it, and, and building them into our existing app and website. And I was leading the design side. Through the pandemic our CPO left. I also ended up picking up a lot of the pieces of the product organization as a result of that. We’re a two-sided marketplace, so there’s another VP of Product. The partner and supply side, which is more commercial. I would, I would say, to try and keep it simple for our audience. And I look at all of the traveler side, so all of the traveler touchpoints, customer-facing in that sense. Particularly our web and our app platform, which is where all of our bookings come through and all of our travelers come and book on our platform. So now I look after that, you know, it’s a big team. It’s around 500-plus, 550 people, 50-plus product teams that look after that on the experience and platform side from software engineers, data scientists, researchers, UX writers, designers product managers, and everything in between. So that’s where I am today and that’s what I look after. And yeah, hopefully that helps give a bit of context. Peter: Yeah. Correct me if I’m wrong, my assumption is that as VP of Design, you were responsible for overseeing all designers on both sides of the marketplace. But it sounds like as you’ve become a product leader, you’re responsible for only one side of the marketplace. So are you still responsible for the designers, all the designers, or did that change? Che: Great question. So that’s still the case. So we, through the, also through the kind of pandemic and some of the changes that we needed to make, and looking at how we wanted to set the business up for the future, there was a big push for the, what we call crafts disciplines, whatever you want to call ’em, so a designer, a researcher, a writer, to report to someone of their craft rather than up into technology or up into product. So I worked with our VP of Engineering to basically orchestrate that with our works councils and all the different labor laws in the Netherlands and everything else, and put together a big plan, that took, you know, the best part of a year to roll out, functional reporting for all of our crafts. So all of design, research, writers across the entire organization, except for a couple of small pockets in marketing, still report up into a UX leader, a senior director that reports to me. So that’s kind of the structure of everything. Engineering reports into our VP of Engineering and, and vice versa. So we have, you know, a data leader similarly for the data and analyst crafts as well. So very much now in functional reporting mode. There’s still some pain points, growing pains and things like that as we mature and we’ve rolled it out, ’cause we’ve always been quite siloed in the way that we’ve done work in terms of product teams and everyone being embedded, now with the craft management structure. That’s kind of a view of both ways of looking at it, right? So, there’s a few things that we need to kind of iron out over time, but the response has been great and the feedback’s been great to date, from, particularly the smaller crafts in design, writing, and research, so being managed by someone of their own craft. We also opened a bunch of director and senior manager roles and more principal level roles at the same time as we scaled that all, ’cause there wasn’t enough in the senior kind of management levels to kind of make that structure work. So we actually had to open and fill those roles before we could actually roll out functional craft reporting too, because they were typically kind of getting stuck at the director level when rolling into either directors of tech or product at that point. Jesse: I think there’s an interesting intersection between culture and craft, in that you can have groups within an organization, practitioners of the same craft that will develop their own culture around that craft, around the implicit values of that craft. I wonder what the implications of that are for your entire organization as you have these distinct crafts within it, with their own distinct cultures, that you are also trying to integrate with a product organization as well. Che: Yeah, there’s so many ways you can slice this. The one that comes to mind, maybe it’s a little bit off track, but it’s kind of the information knowledge transfer in an enterprise company is, is quite challenging. We have over a hundred product teams across the entire landscape. Designers and writers and all of those research and stuff are still embedded. So those crafts now report up into their craft managers. I think it’s, you know, there’s overlaying strategies. There might be a design strategy, a writing strategy, a product strategy for, even for a particular area. Some of them need to more global. So connecting the dots, as a lot of people probably like to say it, from a UX point of view is actually incredibly important. But how you do that through the lens of each of the crafts and execute on it with, in our case, a product-led organization that is moving from being transactional to very much traveler, partner-centric in the way that we think, all the way up. So we are also going through a cultural shift that I think gives more of a voice to that UX community that hasn’t felt like they’ve had much of a seat at the table because it’s been very data, transactional, product-led to date. So I think we’re moving to more of a, much more kind of cross-functional. The voices are there, the, the right leaders are kind of in place to be able to bring that information and knowledge transfer and collaboration together to build great products. I mean, I think, I hate the idea of any of them doing anything in isolation. I, it is always feel like the best things that you make, particularly in big companies, are when you get the right people together and give ’em the space to go and do it. Whatever their skillsets might be that are needed for that particular thing. So yeah, the craft bit kind of, it’s, it’s unlocking it, right? It’s finding the best way to not feel like they’re stifled or cornered or aren’t able to bring all of their knowledge and skills and the information, like I said, to the right places and make the right decisions. From Transaction to Experiential Peter: So I’m familiar with Booking.com because I was supporting OpenTable when Booking or Priceline Holdings acquired them. And I remember hearing about Booking having these very of atomized product teams. It was very A/B oriented and very transactional, very kind of inspired by Amazon or Spotify. It sounds like there’s an evolution though now happening. I don’t know if it’s away from that transactional model, but let’s say towards something that’s rooted in customer types and their experience. What was the impetus for that? Is, is that something that was happening before you joined and you were brought on to help make that happen? Was that something that you recognized and were able to help others realize the opportunities? What was the, yeah, the instigation for, for that shift? Che: I was certainly kind of one of the voices. It felt like one of the few when I joined— a, a smaller group. But I think that has kind of grown over time. It’s certainly from repeating the same messages. I also, you know, I’m senior enough in the organization to get the attention of the right people and have trust with the right leaders to be able to build that. The statement of transactional to traveler-centric or, and partner centric is not necessarily… it’s not black and white either, because everything we’ll do, we’ll still have data that we look at behind it. But I think it’s that we want to actually put some kind of standards and quality around some of the things that we’ve done in the past and be able to do mid- and longer term thinking. Everything has been much more short-term driven. So when we look at you know, what people will talk about lifetime value, metrics, equity, how you measure that of a customer, all those things over a much longer period of time so that the things that we are doing and shipping to travelers , more in the mid and long term thinking, not just the short term. So it’s basically expanding the way our toolkit and the way that we build product. That’s the best way that I could probably articulate it. And then how we instrument things and measure them is not purely based on how many bookings per day we get, but a whole range of other metrics, like that lifetime value, but also based on priority actions and behaviors of customers through different journeys of our products rather than based on like small parts of a screen or a screen itself. So that’s, you know, that’s a huge collaboration, a huge shift in the way that I would say we work. We’re still on that journey, but it’s gonna be, it’s a long way, too. We’ve also articulated a product vision around how we will develop what we’ve talked about for three-plus years, the connected trip, and how that will then come together over a period of time, the commercial side, but particularly from the traveler side. Peter: Did you have to make a business case? Like how did you, you mentioned building trust and because of your seniority, you, you had the relationships. But in a, in a company that can be so data-driven or metrics-driven, what was the language you needed to frame this evolution in, such that others would be receptive to it? Che: Right… So very early on there’s a whole host of things that I did and other people did as well, but the things that I did that I had control over, so when we were looking at, let’s say, let’s just take something design and kind of engineering-centric, like a design system. So as we’d scaled some of our new products, like flights and things into the Booking app and website, we’d basically done that intentionally quickly to validate where the customers wanted those products within the Booking.com brand and Booking.com products. But at the same time, the teams that went and did that built them in different ways. So different technology stacks, different front-end frameworks, new design systems emerge. ‘Cause it’s just such a big company and everyone’s moving so quickly. But we didn’t have a strategy to pull those things back. So I think one of the things that I did early on was actually a presentation to Glenn, our CEO and a few senior leaders, and said basically, here are all of our supply verticals. But there’s a bunch of horizontal things like the customer experience that you want to get to this connected trip. If you look at each of these verticals, within each one of them, you can see that we’ve built a whole bunch of things in different ways. Now that was great to get us to market really quickly, but now as we scale ’em, we’re gonna have to unwind a lot of that. There’s a lot of technical debt. It’s stopping us from like, our velocity is reducing, we are having to maintain five different design systems, et cetera, et cetera. Right. So then I was able to, through the way that the company operates, through planning, you know, get into the practicality of it and the planning cycle, which has a financial component that is the kind of key driver of the cadence and timelines built. You know, I listened to the kind of motions of the business, so to speak, and then came in at the right times and said, here’s what we need to do. Basically put objectives with senior leaders across the entire company that were outside of my remit, to wind back some of the design systems and consolidate them into one. And we did that with a number of different programs. So it was kind of multi-pronged. You know, some other examples, and now as we roll out, example, kind of a much more kind of inclusive design. ‘Cause we, you know, our mission is to make it easier for everyone to experience the world, needs to be more accessible, all of our product landscape. There’s a compliance side of that with our holdings company. So we’re roll– rolling out a big accessibility program at the moment, which is around not just kind of making things compliant, but also doing the right thing and the way that we build that into the DNA of the organization going forward. It’s not a program that someone’s running, it’s actually just the way we do product development as a whole. So, those things are changes in the way that people develop. It feels like another thing on their backlog to do, but like, you’ve actually gotta build it in a way that everyone understands it, values it, and then it becomes part of the way that they work going forward. So that’s changing the way that we work as well. Jesse: I’d love to hear more about going back to that transition that you…

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36: The Chief Design Officer as Corporate Executive (ft. Jehad Affoneh) Mar 06, 2023

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Transcript Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, And we’re finding our way Peter: navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show, Jehad Affoneh, Chief Design Officer for the restaurant point of sales system Toast, joins us to talk about driving an experience strategy across functions beyond design, dealing with tricky executive stakeholders, and how his background in engineering informs his work now as a design leader. Peter: Hi Jehad, great to have you here. Thank you so much for joining us today. As you know, we’ve been talking to folks who have a title of Chief Design Officer, SVP of Design, SVP of UX trying to better understand just what this role and responsibilities entails. So that’s what we’ll be digging in with you today. So thank you for joining us. Jehad: Thanks for having me. Peter: Awesome. So the first question we’ve been asking everybody, and we’ll ask you, might as well start on the top rope: How do you define the role of Chief Design Officer? That is your current title at Toast, I believe that was your title at Splunk. What, what does that mean? What are the responsibilities? How are you held accountable? What does your leadership want from you? All of that. Defining the Chief Design Officer role Jehad: So first of all, thanks for having me. I’m excited to chat with both of you. If you think of the role of any kind of executive team member, there are three main things you’re doing. One is your discipline’s contribution to the business. So if you’re the chief, you know, technology officer, you’re leading technology for the company. If you’re the chief people officer, you’re taking care of culture for the company. So your discipline’s contribution to the company. The other one is how you’re building your team and how you’re building that organization that drives that work, and bringing talent, hiring, growing talent, setting up the right culture for that team to, to bring the right culture into the company. And then how are you uplevelling that discipline or the contribution of that discipline to the, to the company continuously? You can track that with metrics, you can track that qualitatively with, with feedback. You can track, you know, there are multiple ways to track that, but that’s, that’s a third piece. So if you think about it that way, and obviously any executive team member is looking at strategy, helping define strategy for the company on, on vision, feedback from customers and so on. But that’s really just comes with the role. Like, if you’re at an exec role you’re helping drive strategy and execution for the company. But if you think of these three areas, the role of a Chief Design Officer is to build, hire, and grow talented designers, user researchers, design ops folks, roles and disciplines required to operate a healthy organization. Build that culture where around, you know, skills and, high quality work and hold customers feedback and voice of customer as, as core to that story, they’re responsible for upleveling that conversation at the executive level and having conversations not just about customers in general, but about the way experiences help shape the product strategy. And then provide language for the executive team to talk about design and user experience. So internally for a team, it’s easy for us to get stuck into, you know, the details of how user research operates and how design operates, and all the language and words that we can use in order to understand how our work is happening externally. Externally, meaning within the rest of the company, outside of the design team. The role of a, whether it’s a CDO or VP of design, is to provide that language where the company can now talk about experience in an intelligent way that helps the company deliver more to it. And this is, by the way, where the conversation, I don’t know if we’re gonna get there, but this is where like most conversation gets stuck on design metrics, but design metrics or experience metrics end up being a shortcut to, we don’t really understand what you do, so could you please, you know, translate it to the way the business operates. But it’s really common language of the business. Peter: You mentioned operating at an executive level. To whom are you reporting? Are you reporting straight into the CEO, into someone else in the C-suite? What’s your relationship with that highest level of leadership in the organization? Jehad: At Toast, we’re still, you know, founder led to some extent. We, we have a CEO, but we have two key founders that lead R&D and Go-to-market. So I report on the product side of the R&D organization. And I’m part of the, what we call the RD exec team, which is the triad CTO, CDO, and the Head of Product. In addition to, you know Chief Security Officer, you know, and other disciplines that are related to R&D, but we operate as that key triad of CTO, CDO, and head of product or SVP product. Peter: Last organizational question, how, what is your responsibility, if any, for like marketing or brand design? Obviously you’re working on product design and UX research. Are you also working on the marketing and brand design, or is that handled separately? Jehad: No, we collaborated very closely with them, but that’s handled as part of the marketing org reporting to the Chief Marketing Officer. Jesse: And are you the first Chief Design Officer they’ve had. Jehad: Yeah, the first Chief Design Officer. They’ve had design leaders in the organization before at different levels. Jesse: Right. What led to the leveling up of design to a C-level function for Toast? Jehad: Yeah, that’s a good question. I obviously have a different part of that story having, having been on the other side, but I think a couple things. One, which usually is the case in organizations, there is usually a believer on the C-Suite that believes in, okay, we, we’ve gotten this organization as far as we can, and sometimes by the way that CDO, sometimes even CTO or other disciplines, but we’ve gotten this organization far enough with what we have. It’s now a moment for us to uplevel that discipline and both bring someone, either, either promote someone internally or bring someone externally to make a clear point about where design now stands or where engineering and other discipline stands. And two, it’s, it’s oftentimes driven by, and I, I think that probably was the case of Toast, too, driven by the market change. Like if you want that level of talent, there is now a, a specific expectations of, that level of talent on what the role will be in the organization. That’s somewhat taken for granted in other disciplines. Like having a CTO is kind of pretty typical thing to have. That change is happening in design now, which is why like, it’s, it’s a novelty to have a CDO in some companies, but it’s, you know, you wouldn’t be surprised that a company is hiring a CTO, for example, Peter: I’m curious what the difference though is between a Chief Design Officer and a VP of Design, who is the senior most design leader, whose boss is the head of product, who reports into the CEO it sounds like you’re in a very similar context as quote, VP of Design. Is Chief Design Officer simply kind of, like, good branding for otherwise a VP of Design or do you see it as actually, “No, they’re asking me to do something interestingly different than if I were called a VP of design?” Jehad: Yeah, it’s actually interesting. It, it really depends on the company. So like, there are times where it’s branding and, and you hear about different roles, by the way, at the C level that have C-level, like chief I don’t know. I, I don’t wanna mention specific roles, but like, I was at a hospital the… Peter: Chief Customer Officer, Chief Data Officer. Every, I mean, there’s chief everything now. Jehad: Exactly, and obviously not everybody can report to the CEO and by the way, sometimes that’s not what you want either. Depending on the maturity of the org that you’re leading, and the, your place in the organization and so on. But I do think– so, so there are places where, hey, chief is a way to, to attract talent. It’s only one part of the equation. If we give that title, we’re able to bring someone in. But really it’s, it’s, it’s internally not a big change. Partnering with other “C”-level leaders Jehad: And there are times when it’s actually not the case. It’s actually, part of the senior leadership team. Part of the executive team. Only people at that level have that, you know, being part of that team. And that means you have, you have responsibilities to the company, owning the actual end-to-end experience and, and sometimes customer experience end-to-end. You are actually accountable to metrics, company-wide metrics, that’s the case at Toast. Accountable to company-wide metrics around experience, around product satisfaction, around customer satisfaction and so on. And the other piece is we, we have been working a lot at Toast to drive, which is part of the hiring of this role, to drive the partnership in R&D around design, engineering, and product. So this role was not just about a single person, but about having triads from the top-down across the whole organization, starting with CTO, CDO, or you can think of it by the way, if you remove C titles, SVP of Engineering, SVP of design, and SVP of product, down to product teams that are operating at a designer, product person and, and an engineer. I think that there’s a lot of debate in design about who reports to who and how reporting works. My opinion is that debate is sometimes misguided around, to do a hot take, to be controversial about, around more about ego of the person versus the actual value that the role can bring to the org. I think the most, most important thing is, are you a partner to your product and engineering partners, or are you or are you a member of one of their teams? Like, are you a true partner to the engineering and product org, and obviously other orgs, and marketing and customer success and so on. Two, do you have the autonomy to actually execute for your org things that might not be popular at the time, but you believe are true? Do you have the autonomy to execute alongside product and engineering versus for product and, and, and/or engineering? And three, are you accountable for true company-wide metrics or, or, or outcomes? Or is that accountability held by someone else? Like are you actually accountable to the company? Obviously everybody’s accountable to the company, but is part of the company’s key experiences or metrics part of your accountability, or are you, you know, delegated that accountability through someone else? As long as you have those three, then where you report to, what your title is, obviously, you know you know, you, you get different access points, having these different areas, and there are extremes, like if you’re reporting 16 levels down, but you have these things, obviously autonomy is not there. But in my mind, it’s less about that and more about do you have these three pieces that make you a true leader in the org. Jesse: The first of those you mentioned is being a true partner with product and with engineering. It’s interesting because we hear so much about the need for better partnership there. And I think that in a lot of cases, the elevation of design to the C-level is intended to kind of enforce that partnership because a lot of people really, they don’t know what a good true partnership actually looks like here because nobody in the room has had that experience. What do you think makes for a good true partnership between product, design, and engineering? Jehad: Yeah, I think obviously every discipline brings something else to the room, but I think a true partnership means true ownership of the overall outcomes of that triad. So, you know, if, if you’re a, if you’re a partner in that team, you’re involved in and, and you have ownership over, how do we come up with the strategy? So, like, what are we gonna go actually achieve next year at any level, by the way, even if you’re leading a team, what ways in which we’re gonna actually go and measure the success of that strategy, and then owning the outcomes of the execution of that strategy, even when it’s not necessarily the execution of your team. So, like, if you’re having a conversation that says design has shipped, but engineering hasn’t, you’re not really a true partner. ‘Cause at the end of the day, yes, you might not be the head of engineering, but you have responsibility as a true partner to figuring out how do the three of us sit in the room and, and drive that level of accountability. In my mind, shared outcomes and shared metrics is, is, is the north star way you materialize true partnership. ‘Cause if you’re responsible for, Hey, look, your metrics as the head of design or leader of the design team or the design discipline is, you know, as long as you ship these three metrics, you ship on time, you deliver a great experience, whatever that means, and you, your team is happy, you’re good if those are the metrics you’re tracking. Notice that none of these metrics talks about actually shipping the product. None of those metrics talk about product market fit. None of those metrics talk about revenue. None of those metrics talk about you’re staying in business. So if, if you don’t really feel accountable for the other metrics or quote unquote other metrics that truly form triad accountability, then you’re not really a true partner. The, the opposite is true if, if, if your engineering and PM partners don’t feel accountability towards experience metrics, they’re, they’re not true partners. True partnership is often formed, together. It’s a partnership. So like if you’re not coming up with the metrics together, if you’re not building the metrics together, if you’re not building the strategy together, if you’re not accountable together, if your rituals are separate, then you know, you might be a great collaborator, but that’s not necessarily the same as a great partner. Jesse: Mm-hmm. That makes so much sense to me. And at the same time, I also hear from design leaders that they want unique metrics for design because they need to provide pro of of design’s unique contribution to the organization and that these blended or shared metrics actually make it easier for design’s contribution to be kind of swept under the rug. Metrics and organizational maturity Jehad: Yeah. And it’s very fair, and it depends on the kind of maturity of the org, but the way I think about it, and I’ve been there too, there are metrics that prove your worth and there are metrics that are actually valuable. And those two are not always the same. Sometimes they are, but they’re not always the same. So as an example, if you’re early on in your design leadership role and the company is early on in their design maturity, maybe the metric that proves your worth is the opinion of engineering and product of you. And that’s not gonna stay the same. And I know that like to many designers or design leaders who are hearing this conversation, this might be like an allergic reaction to that statement. Peter: Let me interrupt ’cause I’m curious if that’s something you’ve had in prior jobs. You’ve worked in very engineering heavy companies, very tech driven companies. Was that something you needed to do to build that maturity muscle? Is that, is this born of your experience? Jehad: Yeah, it is. And, and sometimes if you step aside and say, let’s say it’s not a mature design team and not a mature organization from the way design is viewed, if you step out and say, I gotta invent my own experience metrics, that I’m now gonna build the whole thing around them to measure them and I’m gonna report on them, but the organization’s not even ready to talk, to have that conversation, instead of proving your worth, you’re seen as like, you know, v…

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35—The Actualized Design Executive (ft. Daniela Jorge) Dec 19, 2022

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Transcript Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, And we’re finding our way Peter: navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show, Chief Design Officer for PayPal, Daniela Jorge joins us to talk about leveraging the superpowers of a designer to tackle the challenges of a leader, the leader’s role in developing the skills of their team, and leadership lessons from her time spent, both inside and outside Silicon Valley. Peter: Daniela, welcome to our show. Thank you so much for being here. Daniela: Thank you for having me here. I’m really, really excited. It’s lovely to see you both as well. Peter: Jesse and I have been talking with a bunch of what I sometimes label true design executives, meaning senior, board- facing, hundreds of people in their organization, because we’re getting more and more of them in industry. There’s still not a lot, but there are more and more, and it’s definitely a trend that we’re seeing as these design organizations evolve and as companies continue to understand the impact that design can have. At PayPal, your role is, at least according to LinkedIn, Chief Design Officer, I’m wondering how do you define that role? What are the responsibilities of the role? How are you held accountable? How do you spend your time? Just what does a Chief Design Officer at PayPal, at least, what do they do? Daniela: It’s probably not too different, I think, than some of my other colleagues who are chief design officers, right? First and foremost, I’m responsible for the holistic experience of our customers, and at PayPal we have many segments that we serve, so that also spans all of the segments. Consumers, small businesses, large enterprises, developers. We even work on some employee experiences too. So, and really thinking about those experiences from acquisition to obviously using our products all the way to online customer support and, you know, as the functional leader, for design or ux, I’m responsible obviously for the craft for how we’re delivering on all of these experiences with cross-functional teams. And then equally as important, nurturing the culture, right? And making sure that we have an environment where folks can do their best work and where they feel like they’re growing and learning. So that’s what I’m, you know, largely responsible for, in terms of where I spend my time. It maps, you know, closely to those responsibilities. The Four Components of Daniela’s Role Daniela: So the first thing is on the strategic end, is really working with partners and with the team on defining vision. So we do quite a bit of, you know, where possible, like, working backwards exercises where we get everyone in a room and we think about what could the experience be for a PayPal developer? What could it be for a PayPal consumer? And then helping to shape that and visualize that so that it can help drive alignment and excitement for what it is that we’ll be delivering for customers. So that’s number one is, almost that sort of facilitation of vision, right? Vision in my mind is a team sport. So we spend a lot of time facilitating those types of workshops. We have a few actually happening this week. The other piece, which was something that we started two years ago, our customer experience reviews. So I’m part of a two- person customer experience council, and we review almost every experience that goes in front of our customers. There are weeks when we have two or three sessions a day, where we’re looking at all of these customer- facing experiences. We’ve done, I think, over a thousand since we started. So, and our role is, is twofold. One is to bring in that, that sort of fresh perspective, right? We, we obviously know what the company’s trying to do, we know what the customer needs are, but we’re not too close to the actual work product. So we’re coming in somewhat with fresh eyes. But more importantly is also connecting dots. Right, Right. So we, we might observe areas where perhaps we’re showing up, like our org chart, which we all know is something that I, I think design is oftentimes trying, trying to address. So we connect those dots, we mind those seams in between teams and solutions. And then also connect teams that should be talking to each other, for various reasons, either because they’re creating redundant work, or again, not necessarily thinking of how one plus one can equals three, if they join forces and how they’re thinking about a customer problem. Then obviously I spend a lot of time, you know, focused on growth and development of the team, so, so running the organization, investing on individuals and their growth and, you know, spending time with my direct reports. And then the last thing is just non-UX or product work. So for instance, I’m one of the co-executive sponsors for Aliados, which is our employee resource group for Latinx, and allies. I participate also in the employee resource group for, for women at PayPal. I’m an ambassador for PayPal’s leadership principles. I do quite a bit of mentoring outside of just UX as well. So these are things that, I spend time on that are outside of what you might think a chief design officer might be doing. Jesse: Mm-hmm. Where Design sits organizationally Peter: There’s a lot there. A lot to unpack. I think we might just be spending our time going through each of these and understanding it. An organizational situational question. And then a metrics question. The organizational situation question is like, where are you in this organization? Right? A lot of even senior design leaders report up through some product function. Is that true of you or do you have a different organization? And then given all of these areas that where you spend your time, what does your leadership hold you accountable for? Are there metrics or numbers or outcomes that they’re expecting you to drive towards? Daniela: Yep. We sit in the CPO organization at PayPal and CPO at PayPal includes product, engineering, design. So it’s, you know, more expansive than just product management. So part of that three legged stool. Though, we, and then we also work very closely with legal and risk and compliance. But we sit in the CPO organization in terms of metrics. We don’t have necessarily hard metrics that I own from an experience standpoint, but we define those per project, right? So if we have a specific project that’s around helping customers achieve a specific goal, those are defined at the initiative level. That’s where more of the hard metrics live. So for us, it’s just really the quality of our experiences. Are we seeing customers call into customer support because perhaps things are not as clear as they should be? How are these experiences testing with our customers? And then are we able to influence roadmaps to make sure that those are being prioritized and that are part of, of a team’s delivery plan. So it’s a bit more qualitative in that regard. And then organizationally, of course, there are metrics, right? Things like attrition and whether or not we’re hiring within a specific timeline. Engagement scores for annual surveys, et cetera. So, in the people area, I would say I obviously have hard metrics. On the UX area, they sit more at the initiative level. And then I think that there’s always that qualitative feeling of whether or not right, the experiences are where they need to be. Vision Jesse: I noticed there’s just a lot of vision work in the description that you laid out. And it’s interesting because I see a real challenge for leaders as they get more and more removed from the roll-up-your-sleeves, do-the-design-work kind of work. Product vision starts to get to be kind of a distant thing for those leaders as their concerns become more business-oriented, more operational, more around the orchestration of the design engine, rather than being oriented around the outcome. To what extent is this an element of your style that product vision is so central to how you perform this role? Daniela: That’s a really good question. You know, as you’ve probably experienced yourselves, I think that there’s always this separation of, of design leaders who are either visionary or operational. And I actually consider myself much more on the operational side, right? What I’ve done is like, I’ve really figured out how to lead at scale, how to work well within, within large companies. I don’t consider consider myself a visionary leader, however where I think I, my strength is, is on the people side. How do you drive alignment? Jesse: Mm. Daniela: How do you drive excitement? And, and to me that’s where vision is really helpful. It doesn’t mean that I’m the one crafting the vision or even that design is the one completely defining the vision, but it’s about how do you get everyone together in a room on calls you know, whatever the, the forum might be, and then have a framework that helps to tease out that vision and package it in a way that’s accessible to everyone, right? That whether we’re showing it to the person who might be leading customer support, to someone in sales, I think that that’s where design has a real strength. And, and where we can really help is to drive that alignment and to also make it feel real so that everyone can get aligned around that same outcome and that same end state in terms of this is the North Star, it may not be, again, that detailed execution plan, but then teams can come up with their own execution plan aligned to, to that north star. Peter: What degree were you the initiator of the importance of vision? Was that something that you helped others around you realize that vision can be a tool for alignment? Or was that something that was realized prior to you, and you’ve been delivering on that? ‘Cause I’ve seen design leaders want to do vision work, but their, their partners are like, we don’t need that. We just need to ship things. And so I’m, I’m just, I’m wondering where the impetus for vision is generated… Jesse: The cultural permission almost. Peter: Yeah, yeah. Daniela: Yeah, it, you know, it, it varies and I would say that it’s probably varied for each situation and also depending on the altitude of the vision that, that we’re driving. Sometimes it might be that there’s a product area, and I might notice that teams are swirling. And people are coming in and it feels like they’re at odds, right? Or, or maybe the team is aiming too low and you’re like, ah, if we could just get in a room and think a little bit bigger and that’s where, not that that I think, you know, workshops, design sprints, whatever it is you wanna call it, not that those are always the silver bullet, but that’s where I found it’s really easy to convince people to just dedicate like three days, five days, to get in a room to, to go dream little bit bigger and to get to that alignment. And every time we’ve been able to then convince people to do that, they’re sold, right? They never wanna want to work another way. They don’t want to kick off planning a different way. So, so that, that’s what’s worked mostly, especially when it’s like at the, that product level, that initiative level. And then of course there have been times, you know, maybe there’s a very senior executive who has a vision and who comes to us saying, “Hey, can you just help us visualize this?” And through that process, you kind of influence the, you know, it a little bit more so that we’re not just the, the ones coloring in between the lines, but again, we bring in an approach where we can also help shape that narrative and, and shape it a little bit more, bring in that customer lens into the thinking. And then of course, help visualize it, right. Since that is a, a key skill that we have. Jesse: Mm-hmm. . Peter: And then how, how do you operationalize a vision, right? One of the concerns around visions is you get these very pretty concept cars. You get these very pretty imagery and videos of some future state experience that then people lose sight of over time and they just go back to doing whatever they were doing. Do you have mechanisms to turn these, this vision work into something that gets metabolized within these teams. Daniela: Yes. And, and again, it, it’s, it’s varied over time. So one of the things that, even though I’ve participated and, and driven even exercises where it was like a five year vision, I, I much prefer to drive shorter term vision activities. I feel like those are, right, much more achievable to, to the point that you’re making. I, I have found that five-year visions are very inspirational, but don’t always translate into action. So one is just picking the right timeframe for, for defining that vision. And then the other piece, which I think is really critical and important is your vision is a rough blueprint. so then you can actually work backwards from it and actually saying, if this, if these are the outcomes that we want to achieve or what we want to eventually deliver for customers, right, what’s the first step? What’s the first version of, of what we’re building, right? Are we going to build a living room, a kitchen, maybe one bedroom and one bathroom, even though eventually we want to have this amazing mansion? So, so I think it’s then that, that discipline of being able to work backwards from that vision and having that first step defined. And then to add to it also not being super precious about the vision, because I think one of the beauties of, of the work that we do is, is what you learn in the process, right. So I think it’s helpful to have that north star, but you also need to leave that open, as for learning as you go and, and for having customer input shape where, where it should go because, and what you may end up in version three may not be exactly what you had figured out and, you know, for that full vision two years ago. So I think it’s about then working backwards for the V1 and then iterating your way towards that end state. Jesse: You said earlier that defining that vision is a team sport. I’m interested in who the players are. And how you call those players to the table when, you know, sometimes the, the interest isn’t there, sometimes the motivation isn’t there sometimes the belief in what you’re doing isn’t there. How do you bring the right team together to create a successful product vision? Daniela: You know, at PayPal we’re really lucky that, that I feel like everyone wants to be included and participate and when, I mean everyone, right, we’ll have legal in the room. We’ll have risk and compliance in the room and, and it’s, those are always the best, in my opinion is when you actually have, not only in terms of what comes out at the end of that five day session, but in terms of then how the project itself plays out, right? Because people were included upfront and they actually have that, that sort of buy-in and that motivation and they understand who the customer is, they understand what, what we’re going to be delivering, what the outcomes are. And then they’re part of solutioning throughout because they were part of, of that inception phase. So, so to me, the more cross-functional, the better, and at PayPal it hasn’t really been a challenge in terms of, of engaging others. When I think about other companies where perhaps that, that has been more of a challenge we’ve been really thoughtful about thinking about the activities and then figuring out, like what’s, you know, how can you make it more accessible so that someone can maybe come in for, like, two hour kickoff on, you know, immersion on customer insights, and then maybe they just come in for like a couple of checkpoints so that they’re not from the get-go saying, “Oh yeah, I have to commit five days” to something that, you know, feels very fuzzy and feels like a, a big time commitment. So, so that really helps. It’s just really thinking about your audience and thinking about how do you close that gap between…

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34: Design leadership to support organizational transformation (ft. Rachel Kobetz) Oct 09, 2022

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Transcript Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, And we’re finding our way Peter: navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show, Global Head of Design for Expedia Group Rachel Kobetz joins us to talk about staying connected to the work while keeping sight of the big picture, getting past zero sum thinking in building partnerships, and the importance of intentionality in leadership. Peter: So Rachel, thank you so much for joining us today. Jesse and I are talking to a lot of truly senior design leaders. And even though we don’t know you directly all that well, you’re working with my co-author Kristen, who Jesse worked with extensively at Adaptive Path. Defining the role of Global Head of Design Peter: You’ve been building a really impressive design organization at Expedia, and we wanted to learn more about that process and unpack that. So thank you for joining us. The question that we’re asking everybody to start, the conversation with, we’re just diving right into the deep end, you’re an SVP and global head of design at Expedia. How do you define that role? Like, what are the responsibilities, to what are you held accountable? What’s that job? Rachel: All right. Well, thanks for having me first off. And you know, the role is rather interesting. It’s a transformation role. So if I think about, you know, setting the vision and the organizational leadership for getting us to become an experience-led company, that’s essentially the bulk of what I do and that’s across three areas. So my charter is to transform the experiences, transform the function, and transform the company, small task, you know. Jesse: Mm. Peter: No, no, no big thing. How– so. So that’s a big definition of the role, how well did they understand that when they brought you in ,that, that this is what they were looking for, was someone to do this kind of transformation, versus you, through engaging them as they were looking maybe just for some design leader, through some engagement with them, you helped them identify this transformation opportunity? Where was that conversation when you started? And I guess now almost two years in, where is that conversation now? Rachel: Yeah, I think it was both, right? So, in conversations I had, even when I was, you know, starting to explore the opportunity, talking to our C-level, our, our CEO and, and all the leadership across the company, there was a hunger, right. To… what is the type of company we’re gonna be on the other side of this thing, right. You think about COVID and all the stuff that was happening at the time, and space for innovation. And space to define what is the DNA of the company, what is gonna be the culture of the company? And there was an understanding that customer experience is our competitive advantage or should be our competitive advantage. And in order to get there, you have to become an experience-led company. Some people call it design-led, but you know, I, I definitely go out the door, calling it experience-led. And in those conversations, when someone says, I wanna become this thing, they have to understand what that takes, right? It’s not just something that you kind of like slap on a poster. It requires transformation of the culture of the company and the way that you work and the way that you operate to get to that point. And so that’s the type of conversations I started having. And so part of it was them having an understanding and a growth mindset of what they wanted to become and how they wanted to transform as a company, moving from transactions to relationships and what that takes. And then the other piece was me having conversations, starting to talk about what that could look like. And so for me, it’s very important, no matter what environment I’m in, that people know what they signed up for. Number One. And, and, Two, that we’re creating the environment for strategic design and we’re setting up the role for success. And so there was a lot of conversations about, well, what does it take to do that? Because just bringing in an executive in itself, if you don’t create the conditions for that executive to be successful, you’re not gonna have the outcomes that you’re looking for. You’re gonna have kind of the, the hero mentality where this one person is going to change the world, versus being able to have the entire environment foster and nurture that type of strategic design culture, essentially. Peter: How long were you talking to them before you joined? Was this over many months, were, how many conversations were there? It sounds like, and, and this is something I encourage, but rarely happens, it sounds like there was a long kind of courtship to make sure this was the right fit. Just, you know, practically what did that involve? Rachel: It was over the span of a couple months, because, you know, I had to make, you know, we all wanted to make sure that it was the right thing, right. Bringing in the right person, making sure the environment was right and making sure that you’re setting the role up for success, as I mentioned. And because the charter is, it’s a large charter, but it’s also for the first time ever, it was to build a centralized function for the entire company. And I’ll, I can talk a little bit about what that looked like, because we were separate brands for the longest time and we were operating that way. And it was the first time ever, they were bringing all the design groups underneath one leader, right. So that’s a major shift. So there was a bunch of conversations we were having. And what that allowed me to do, though, is to get to know everybody, right, to understand what you’re walking into and who are gonna be your partners, and then to also set the stage and create the runway. So the leadership at the company was setting the runway for people to understand what’s the charter of this person coming in, in the role, what are they here to do and how can we best support them and partner with them. And so that, that amplifies or accelerates the level of impact you can have in the first year, cuz as you know, the first year is usually foundational work. And so that accelerated the amount of impact I was able to make in the first year in that foundational work. Stuff that would’ve taken probably a year or a year and a half was like the first six months. And so that, that to me was major. That sets the, you know, sets the ground for awesomeness in my, in my mind. And because this, this centralized function works across the entire company that is, you know, you know, creating and defining experiences for travelers, partners, agents, developers, and employees. And so there has to be this, this galvanized support or this, this, this like coalition of the willing, right, across the company that is, you know, not just interested but aligned to what that means. Establishing relationships with your existing leadership team Jesse: It seems to me that one of the most crucial groups of partners for you to recruit, to achieve these kinds of outcomes so quickly, are the people who would be your direct reports, the people who were the leads of these individual brands, who previously had, you know, their own domains entirely, never had to think about anybody else’s problems. And I’m curious about how you went about establishing those relationships and establishing a way of engaging them, engaging with them and engaging them with each other at this larger scale. Rachel: Great question. So definitely, when you wanna build a world– world class organization, it starts with bringing in world class talent. It, it’s a mix at my table of people that are subject matter experts and have been in the company for a while, and, you know, kind of people that have been there a couple years and people that are net new. And I think that’s a great mix to bring in so that you’re not just like completely flipping over the table, but you’re bringing the, the best-in-class individuals for the specific roles that you need. And so I did a couple things. I identified what are the needs for each of the roles to be successful? These are pivot roles, right? To your, to your point. Like these are crucial roles and they have to operate as a first team, right? They cannot operate… they can no longer operate just in their domain and just their group. They have to actually operate as a first team, together, in order to get the best possible outcomes, and also to be able to work across and up, across the company. And so that was really important to me. So it, part of it is the dynamics at play, of, like, the expertise, the personality, how they show up, what is their, you know, what is their presence? Who are they gonna face off with in the company and how are they gonna be successful in those environments? And then what are the embedded capabilities that I needed to build? What do we have today versus where do we need to get to, to be strategic design, right? As far as like, what, what, we didn’t have design operations, right? So that was one of the first things I went after to build. We didn’t have service design, you know, you think about all these different capabilities. We had to be able to build them and, and start those practices from scratch, the ones that we didn’t have. So it was very important for me to bring in the right leaders, bring them together and have them start to have the mindset and behaviors of operating as a team, not just a bunch of high performance individuals that happen to work together. Jesse: Mm-hmm mm-hmm. Peter: While all these designers now are reporting up through a single centralized design organization, have you maintained teams that are brand by brand, or did that all get kind of shaken up as well? Let me start with that question. Like what are are, because, well, actually let me not start with that, just that question, because you mentioned service design, right? And so I’m wondering with service design, is that looking across brands, like in some broader holistic experience, what is the interplay with some of these more strategic, centralized design functions and what I would imagine in a company like Expedia, and you have Expedia, and you have VRBO and you have all these distinct brands that I would imagine there’s teams specific to them. How does, how does that interplay work? Organizing by customer and their journey Rachel: Yeah, that evolved. So, we instead organized by customer. So, when you think about the traveler, you think about the journeys for the traveler. There’s a lot of similarities across those journeys and you’re designing for those journeys, right? So instead of just having a VRBO team and just having a brand Expedia team, even though we’re building out those brand experiences, we’re actually looking at it more holistically. So we’re looking at the end-to-end across the different phases of the journey. And those things are very similar, right? You think of, you know, I am in discovery mode, I’m in dream mode. I am shopping and I’m booking, right. You’re working across those journeys. And so it was it was a shift in mindset to be able to then look at things crosscutting and look at things more holistically instead of looking at them either only by brand or only by specific function or feature, which was a, which was a shift in the company. And so being able to start having conversations about end-to-end, allowed us to start to shift that mindset from product roadmaps to experience roadmaps. And, and that makes it so that we’re talking about, well, what are we delivering? What value are we delivering for our customers or for our travelers? And, and then what are the things that need to be true? What are the services and capabilities that need to be able to light up that experience? And that’s a different way of working. Jesse: Mm-hmm.. Peter: Is is that end-to-end specific to design or did product and engineering also adopt this structure? Rachel: They’re looking at it the same way. And I think, I think that’s required. None of this stuff is done in isolation. It’s so important to have very strong partners in the different functions so that you can be doing this together. You know, we, we talk about it as not just three in the box, talk four, box– four in the box, sometimes five in the box to be able to get this done, ’cause we’re working with, you know, data science. We’re working with ML, we’re working with marketing and brand, right? So they’re at the table as well, not just product, design, and engineering. And so being able to look at things more holistically, everyone’s at the table and caring about the quality of the experience. And I think that’s where you get success. Jesse: So in engaging these partners, it seems that you must have gone through a process of some education, some evangelism, some reframing of design, its role, its value to shift it toward this more strategic emphasis. Tell us a little bit about how that went for you. Rachel: Yeah, sure. You mean the road show? Jesse: Yeah, sure. Rachel: yeah, Peter: If that was part of it, yeah. Rachel: Yeah. I mean, it depends on the level of maturity in organization, right? So if you have an environment like like Expedia, where you had a world where there were multitude of brands underneath one umbrella, and they were all operating as separate companies. You could imagine that when you bring all of that together and you’re looking at it and delivering as one company, you’re gonna have different levels of maturity throughout the organization. And so we had some parts of the organization that were already operating, like, operating like mini Frogs and IDEOs, right. And then we had other parts of the organization where design was an execution arm, right. Or operating a completely different way. And so because of that, it was a– it’s, it’s mixed. I always talk about when you’re going through change management, it’s gonna be mixed maturity across the board. You’re gonna have some people that just get it and wanna drive with you and, and they’re ready to roll. And then other people have to be educated and brought along in order to get to that place. And so, it was a mix. It was a mix of finding the people, when I mentioned coalition of the willing, it was a mix of finding those people, and those people that could be champions with me, those people that could be the, the beacons. It’s really important to find, not just the individuals, but the projects or programs that can be the beacons to showcase how a new way of working yields better outcomes. And so that’s part of what I did. So part of it was a little bit of a road show talking about, like, what does being experience-led mean? And what does that mean for the company and how does that translate to how all of us show up every single day to deliver a better customer experience? And then part of that was bringing people along and using programs themselves to then become those, those proof points or those case studies of this new way of working. And then you get to a point where you’re leaning into operating models, right. And, and codifying those operating models. And then, you know, part of my job is delivering for the business, right. And so becomes a measure what you’re doing. So benchmarking what you did before, and then measuring the, how you’re moving the needle is critical to be able to also then bring up people along that don’t have that same mindset initially, where they’re already in it. Like they already get it. They, they actually need to be convinced. Usually the data is what can do that. Communication strategies and tactics Jesse: Hmm. You mentioned creating these beacons that showcase what’s possible and kind of can lead the way for the organization, and one of the challenges in an organization of your scale and of your complexity is just getting the message out about your successes, especially in these environments where people have histo…

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33: Leading Design in a Product World (ft. Greg Petroff) Sep 18, 2022

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Transcript Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, And we’re finding our way Peter: navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show veteran design executive Greg Petroff, formerly of GE, and now head of design for Cisco Security, joins us to talk about how to be the first design executive in an organization, the role of design in defining products and transforming organizations, and some reasons for hope in the evolving relationship between design and engineering. Peter: So we have with us today Greg Petroff and Greg, the reason we wanted to have you join us is Jesse and I are pursuing a topic in particular around what does it mean to be a design executive, like a true design executive, not a make-believe design executive that I think a lot of folks are, but like real deal, very senior, in board meetings, access-to-C-suites kind of design executive. And when we were thinking about who to have on to address this type of topic we thought of you. You’ve done this role in a few different firms. You and I, when we’ve…. just over lunches and, and whatnot, I found you to be very reflective in thinking about what it means to be a design executive. So that’s why we wanted you on, so thank you for joining us. Greg: Thanks for inviting me. I’m happy to be here. Peter: It’s an interesting time for you, ’cause you’re about to start a new design executive role and I’m wondering, and, and you’ve had a moment or an opportunity to reflect, I think on just what it means to be a chief design officer, an SVP of design. I don’t know if you have a favorite title, even we can get into that, but like what is, what, what was that journey of considering a new role? Like and how did it inform kind of your definition of what it is that you do. Greg: Yeah. I mean, it’s interesting. I had an opportunity this summer to take some time off and spend a little bit more time entertaining offers than I, I probably normally have in my career. That I think helped me get the right kind of perspective about what would be the right next role for me. And, you know, if you remember Peter, you and I actually met in, in Berkeley and talked a little bit about this a couple months ago, you know, in that early part of that thinking. And I think it comes to a couple things. One, there’s sort of what I’d like to do, but there’s also what I’m good at. And, you know, you kind of have to recognize the two and you know, there’s one thing that, you know, I’ve done successfully over the last few years is create balance teams that perform well. And, you know, I sort of see my role as being someone whose design problem is the practice of design in the organization I’m in. And and as much as I love being in the details of the individual design decisions, which I like doing, you know, my, my strength is more in empowering other people to, to be successful. And of the opportunities that were sitting in front of me there were, there were sort of small, medium and large. And you know, I was really intrigued with the role that I am taking, which is I’m gonna be the Chief Design Officer for Cisco Secure, which is the secure business at Cisco. Very large organization, actually fairly mature with a lot of strong design leaders already in place. But also some challenges from a transformation perspective, you know, Cisco went through a whole bunch of acquisitions over the last five years. They’re, they’re, they’re struggling with coherency. Some parts of the business are, are really effectively managed really well from what I can tell, and other areas, you know, need some TLC and, and some nurturing to help them get better. And at this point in my career, you know, I feel like that’s a good spot for me, like an environment where I can be an advocate for the other design leaders in the organization and, and hopefully set them up for success. Defining the role of Chief Design Officer Peter: Well, what does it mean to be a chief design officer? Was that something that they said they were looking for? Was that how you kind of shaped the role? What, what, what is that? Greg: Wow. I, I think we’re early in trying to figure that out. They defined the role as chief design officer, so that was interesting to me because they, they had thought through a, a certain, you know, executive leadership level. The CDO has sort of three interfaces, you know, they have the interface up, which means that they’re spend time in relationship with senior leadership and an organization all the way up to the CEO and board and are advocating for design to, you know, people in the organization who may not actually understand the value of design as much as they could. And, and if they understood it better, you know, the organization probably would be more successful. And then there’s a second interface level, which is, you know, you’re sort of leadership peers. So you know, your head of product, head of engineering, research, the, the marketing team, but people who are, you know, the SVP and VP level in the organization, and working with them to, to recognize how to successfully, you know, implement and empower their design team so that they’re getting real value and impact out of them. And then the last interface is really about creating the conditions for the design team to be successful. And, you know, and that’s really connected to making sure that, you know, people’s incentives are aligned, right, that you’re, you know, growing your people and your talent, that you’re empowering them, that you’re finding ways to give them agency and, and you’re kind of building a growth mindset culture. And I, I think a big part of a CDO’s role is to be actively engaged with the whole product life cycle. So not just design’s role in the product life cycle, but, you know, co-creating that with your product and engineering peers, so that there’s a shared understanding of everybody’s role in creating great product and, and, and really trying to, not build a us versus them culture, but you know, a product culture that really wants to drive impact. And, you know, CDO’s job, I think, is really to kind of wear that hat as a, you know, a partner in the organization towards, you know, really try to make impact. Being an organization’s first true design executive Jesse: I have the impression from the work that you’ve done, that you’ve often been the first person in these organizations with that level of executive responsibility over design. Is that accurate? Greg: Yeah, that has actually sort of been my M.O. You know, when I joined GE which was 11 years ago, which is amazing, you know, I became a chief experience officer at GE Digital and, and there definitely was a vacuum in terms of the understanding of design and, and it was the first time for that role. You know, I think along the path, it’s similarly, you know, ServiceNow, my time period there was a new role. They consolidated a couple of different design groups under one leader. I was the global head of design for that team and, and started build a, you know, a singular culture for the design organization. Compass, where I was most recently had a leader before I arrived, but not an executive level support leader. So it was sort of, again, a new role. And at the, in Cisco again, yeah, this is the first time that they’ve actually are building a CDO into the role. So who knows. We’ll see what happens. Jesse: What are some of the challenges for being the first one to step into that executive level leadership of design? Greg: I, I, yeah. Wow. I, I’ve certainly made lots of mistakes. Yeah. So, I think you need to build trust with the team, right? So the folks that are working for you, have to feel that. The things that they’ve brought to date are, are valid, that you know, that you’re not gonna rock the boat too much. You may shift things or change focus on areas, but you know, you need to gain trust of your design colleagues and the design organization as a whole. So that’s kind of a first step. I think selling the story of design, the narrative, and getting that story, you know, so that people understand the value is something that every senior leader has to take great care at, and it’s a balance because design— the impact of design can take time. Yet senior executive attention span can be quite short. And so you have to find ways to show demonstrable quick wins and benefit, while leaving room for the things that, you know, that are actually more substantive and impact-driven, that are gonna take more time. And, and in a way, like you have to move chess pieces before you can actually get to the, you know, the outcome that you’re looking at. And the, one of the things I’ve learned is that you have to make sure everyone understands each time you move a chess piece on the board. And you can’t just do that in a vacuum. I, I made that mistake where I’m like, you know, I’m responsible for the outcome. They got me here. I don’t have to tell ’em everything we’re doing as long as I deliver. And the reality is no, you really do need to spend time and say, “Hey, we’re gonna do this. And here’s why we’re going to do it.” Peter: Who, who do you need to spend that time with? Are you, is that your leadership? Is that your team… Greg: That’s with leader. That’s that’s with leadership. Yeah. Specifically, you know, I think it’s, it’s, multi-level. One, it’s with the, your direct. So, the person that you, you know, report to you know, and in, in every instance I’ve always been reporting to a chief product, you know, officer in, in the relationships I’ve been in. So, making sure that the relationship between you and that person is airtight, that you are communicating regularly, that you’re aligned, that you understand their objectives very clearly. And that the things that you’re going to do are going to connect to their objectives. And at the same time, you have the, hopefully, the transparency and trust with that individual to bend those objectives if you feel that it would benefit the outcome that they’re looking for, like to, to sort of say, I understand what you’re trying to accomplish, and to get there, maybe we take this path because, you know, my experience says that this might get us there in a more fast or, or effective way. So that’s, that’s, it’s really important to be crystal clear at that level. And then at some point early in your tenure, you have to sort of set a vision for your team. Because design teams in general have to feel like they’re connected to something. They have to have a sense of purpose. And, and that adds clarity, actually gives them autonomy because they can see how they might contribute to that broader perspective. And so it, you know, at some point in, you know, as I’m imagining myself going into to my new role, which starts next week, you know, I don’t know, will, it’ll be six months or nine months, but some point in we’ll come out with a picture of what the future might look like. And we’ll, co-create that. It’s not gonna just be, it’s not coming from me. I’m gonna actually have the team help us build it. But then we be very transparent about that so that people can identify with it and align themselves towards it and say, okay, here’s how I can contribute towards that. Setting a Vision for your team Peter: And when you say vision is this, like a literal envisionment, some future state experience, or is it more a direction we’re heading in and desired outcomes and impact, something kind of a little more, maybe a little less specific, a little more vague, but that allows folks to fill in the picture. Greg: It’s a little bit of both. You know, I’m a big fan of north stars. I don’t think you actually execute on a north star. You use north star to drive the art of the possible and to, and to scratch the itch on like, tough questions. And you know, words are valuable, but artifacts are more tangible and easier for people to, especially our community who are visually oriented to, you know, identify with. But you have to do them, you know, in a way where people have permission to break them and, and change them and, you know, and, and, and, and challenge them and say, you know, we’re gonna come up with something different based on, you know, the results that we have. And then I think there’s a fair amount of of brand work. I think, you know, working with the marketing team is actually really important to sort of understand how they want to sell the product, how they want to pitch products. What’s the, what’s the, what’s the onboarding process for customers? I mean, it’s not enough anymore just to design great product. You have to actually understand how people learn about the product, how the product is sold to them. What’s their first set of experiences using it? What happens, you know, after they’ve used it for a period of time? And a lot of that connects to the overall narrative, the story you’re telling as a company, not just from the, you know, the UX perspective, but the brand perspective and a big part of what I will work with you know, with my marketing colleagues is understanding how they’re positioning, you know, the security business at Cisco and, and making sure that the work that we’re doing aligns with that as part of that strategy. And, and so we’ll probably have a, a, you know, a couple of documents, one that sort of like a brand house with very descriptive kind of levels to it that, that describe the kind of experience and the principles around that experience that we’re trying to deliver that’s connected to how we’re gonna tell the story and the narrative, and then we’ll have some future looking artifacts that tell a story about what it could be. And then, you know, we’ll look at the period in between that and start working towards it. Peter: At GE, Beth Comstock– it was, my understanding was Beth was a, a main advocate for building out this design and UX center of excellence. And I also believe she was a chief marketing officer. Were you, what was that? Were you in her org? Were you reporting up to her? Greg: Yes. When I joined GE, I reported to Linda Boff who worked for Beth. And I had a very direct relationship with Beth. She was one of the great mentors in my career. She, there’s a really funny thing. My very first day at GE, I met her in, you know, GE’s corporate offices in, at the time were in Connecticut in this just sort of, you know, massive complex. And she had one of those offices that, you know, was just enormous. And, I walked in, I had the temerity to ask her this, uh question. I said you know, “on a scale of playing it safe or getting fired, you know, like where do you want me playing in this role?” And she said, “as close to getting fired as possible. And I will give you a couple of get out of jail cards.” Um, and uh, it was awesome. It was like a really, you know, empowering thing for a leader to say. And, you know, we, we, we did some things in the first two years when I was there that were difficult to do and, you know, were sort of courageous acts, but were the right things and, and it was really great having a leader who really supported you in terms of doing that. Peter: You mentioned you’ve been, I guess, more recently reporting up through a chief product officer, but there you were in marketing. And I think that’s a different experience than a lot of design leaders have. The ones at least that we engage with, right, ’cause we tend— typically are talking with UX and product designers who are, are reporting up through product. What, what, what, what was that experience like? I know that’s a weird question, but, to report up through marketing, but, you were also responsible for creating product and doing user experience work. Was that a, a happy and healthy relationship? Was it weird and, and kind of fractious, because there were different masters that you were trying to serve or how did that all shake out? Greg: Yeah, well, it did shake…

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32: The Intentional Design Executive (ft. Kaaren Hanson) Sep 05, 2022

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Transcript Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, And we’re finding our way Peter: navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show Kaaren Hanson, chief design officer for Chase offers her perspective on what she had to learn and unlearn on the way to the C-suite, how the leadership challenge changes as you move up, and creating design teams that leave a lasting impact on their organizations. Peter: Hi, Kaaren, thanks for joining us. I’ve been working with you now for couple of years, almost a few years in a couple of different contexts, and I’ve seen how you are leading these sizable teams, particularly inside a couple of banks, and Jesse and I are pursuing a thread right now, which is What does it mean to be a true design executive? There’s a lot of people with design leadership roles and titles, but there’s not a lot of people who are operating at an altitude that I would consider errr… Being a real executive. And, and you’re definitely one, given the size and scope and scale of, of the operations that you’re responsible for. You’re currently the chief design officer at Chase. Is that right? Am I getting that right? Kaaren: Yep. Defining the role of Chief Design Officer Peter: Okay. So what, what is that role? What does it even mean to be a chief design officer at Chase? What do you, what, what are the responsibilities? What do you do? How are you held accountable? Kaaren: Yeah, those are good questions. So, you know, it’s interesting ’cause I think about this as the role evolves over time. So right now, what I’ve really been focused on is: first, how do we create a truly strong and robust design team? One that has strong leadership, one that has strong craft. One that is appropriately resourced. And one that is integrated into the business yet is also able to go up an altitude, so they– we can look at the end-to-end experience. So that’s been a big push of mine for probably the last year and a quarter or so. And I’ve been there for about a year and a quarter. And just in that time, for example, we’ve grown from about 300 people on our team to about 800 today will be about 850 by the end of the year. And by the end of the next year, we’re gonna be about a thousand. Which is a lot of growth. Um, so you can imagine I was spending a ton of my time hiring, but also a ton of my time working with leaders across the business, including, like, the CEO of consumer bank or the CEO of connected commerce or the CEO of wealth management, to ensure that design is sitting at their table, and that the operating mechanisms are supportive of us being customer- focused, customer- first and really starting to hold a bar. The other area that I’ve been focused on is metrics. So any executive knows like metrics fricking matter, right? You manage what you can measure and we can measure customer experience. We’ve all been doing this for years. Sometimes just more systematically than others. So one of the first things that I did when I joined was to connect with our data science team and to really work with them, they are very excited about customer experience metrics, and they were thrilled that someone else was excited about them and championing them. And so as you just need two different voices in the org to really make something happen more quickly. And so we aligned on three key metrics that we’re using for our customer experience. And then it was all about how do we make sure every single team has customer experience metrics that ladder to the bigger OKRs of the company. So for example, one of the OKRs that we have is Net Promoter Score of at least 70, right, which is a, a reasonably high bar. And then we can look at well, what impacts that net promoter score and some very basic areas. Customer success rates, right? If you’re not successful, you’re unlikely to be very happy, right? It seems super obvious. We can easily empower teams to go after that success rate. We’re using something called a customer experience gap. This is something the research team started before I joined. And essentially what it does is the lead researcher, lead designer, lead product manager, do a heuristic evaluation of the five most common tasks. And they note all of the gaps that are present. And then we figure out, What severity are they, one to five. Five actually prevents you from accomplishing your task in some cases. And one is more like, you know, padding this size, that size. And so once we’ve got those in board, then it’s about how do we start to change the way that the company views our products? So now I’ve been working with the people who operate the bank to make sure these customer experience metrics are part of the business reviews. They’re part of the quarterly business reviews. The CEO is asking about them. They’re part of monthly updates. And this helps the teams to focus on them. While at the same time, we’re really building this muscle of strong design-research-content, et cetera, that is able to help the teams on the ground become much more customer focused and rigorous in that way. And then at the same time, what I’ve started to do in the last three to six months is focus on how our design, product, engineering, and data working together. And toward that end, we’ve been bringing in Silicon Valley Product Group. They do a really good job really helping teams to understand that together, they are collectively there to understand the customer problem, to solve, to figure out how the heck they’re gonna measure if they made any difference, and to just go fast. So I’m looking at it as you know, there’s this system that’s in place at Chase. And my job is to figure out how to use whatever judo moves I can to make it a system, you know, that supports the customer and creates conditions in which our teams can do the best work of their lives. And when I think about our teams, our teams are not our design team. Our teams are our product managers, engineers, data, and design. Peter: So you’re, you’ve clearly thought about this, ’cause ’cause you had these four bullet points ready to go: team building relationships, metrics, product management. You’ve been a reflective leader. I’m wondering when you stepped into the role, did you know that’s what the job was? Is there a, are you working from a playbook or had you so, so, so you, so you’re, you’re shaking your head uh, which the, audience wouldn’t be able to see. So how did you, what, what– did you have a playbook coming in? What did that look like? And then how did you unpack that these were the four kind of initiatives to engage in? And it sounds like in roughly this order, like how did that come about? Kaaren: I mean, well, like, you know, anytime you start a new job, your first thing to do is to just listen and learn, right? And to figure out what’s going really well. What are the points that you can really shine and amplify, right? Like those CX gaps, huge point of light, all you have to do is help amplify it, right? And then also what’s not working as well. And what doesn’t make sense. And then, you know, I took a lot of notes and I thought about, wait, what’s going on? Where’s this? And I thought, okay, which of these could I make progress on quickly versus more slowly? I have tried a lot of different things, some of which were taken up like this, and some of which were not. So those customer experience metrics, that was a huge surprise to me how quickly it happened. I thought it would take two to three years. So I got started and I was like, all right, we’re gonna go, we’re gonna try this. And literally, yeah, within six months it was present in 70% of the dashboards that teams were working towards, like blew my mind. I couldn’t believe how quickly this company moved. If I had my plan, I would’ve said I was gonna do that for the next three years. So that was a nice surprise. There’s some other things though, that we’re still working on, like the ratios, the ratios of designers to product managers, to engineers. They’re not where we should be. And I’m trying to hire as fast I can, right. While still holding a high bar for talent. And I am not making enough of a dent on these ratios. Right. And so that is something maybe I thought would happen more quickly and it’s happening more slowly because we continue to hire all over the place. And so, you know, so I, I think a part of it is also just seeing, well, where is the organization? What is going to get traction, right? There are probably 10 levers to pull that will make a difference. Let’s try one. If the org is ready to go with it, awesome. If they’re not ready yet, that’s okay. We got nine others. And so I’m very, yeah, I don’t necessarily have a playbook, but I do feel very strongly, the first job as a design leader coming in is to create a strong, robust team. Because if your team isn’t robust, there’s no way you can push for change. Jesse: Mm-hmm , I’m curious about where they were when you started, what was their approach or attitude toward design when you came to be the face of design to the leadership there? Kaaren: Yeah, I think it’s hard when you have organizations of this size, because it’s so, it’s so variable depending upon where you are, and depending upon the people. I will say what really impresses me at this company is the people are incredibly smart, but they’re also so darn open. And in fact, when I first joined, I was like, really? Are people really this nice? Like, hmm, is this just an act? You know, like when am I gonna learn that it’s not true. And I still haven’t learned that it’s not true, right? Which is astonishing. So really smart people open to trying new things. Maybe they just under didn’t understand the rationale for why this mattered. So a lot of what I’m trying to do is articulate the rationale for why I’m doing something and why the team is doing something. And one of the trainings we’ve brought in, we’ve brought in two really important trainings for the design team, meaning design, research, content strategy, et cetera. But one of them is Articulating Design Rationale with Tom Greever, right? And what that’s all about is, how do we help our team to better articulate why they’re doing something and why they think it’s important? Because usually if people have the same information, they come to the same conclusion, right? It just helps the overall broader team operate more seamlessly. And the second one is Facilitative Leadership. A woman named Wendy Castleman has been helping us with that. And it’s really about how do we help everybody on the team drive alignment if there isn’t alignment and particularly that alignment on the customer, right? And again, like we’re getting better in pockets, you know, it’s faster in pockets, but overall it’s just a foundational skills we expect everybody to have. And sometimes I’ll talk to people and they’ll say, wait, I thought that was product management’s job. And I’m like, yeah, it is. And if the team you’re on, isn’t aligned, well, you go fix it, right? And it is so important. That’s why everybody needs to do it. The need for prioritization Peter: You mentioned going your team growing from 300 to 800. Was that real– was that a realization that had occurred before you joined and, and they wanted to bring you in as part of this expansion, or was that part of your listening tour? Where, in looking around and reflecting, you’re like, wait a moment, I see one of– a way forward is we need to grow the team in order to address the challenges that I’m hearing about. Kaaren: I would say it’s yes, and. So I think when I joined my charge was to grow us from like 300 to 500. Right. Which was sizeable. And then it became clear that, you know, that wasn’t nearly enough. And now, by the way, I’m the one that’s saying we’re not growing to more… by more than a thousand. Like we’re not, and I’m getting all of this pressure, yeah, but we want 60 more people and I’m like, get in line. Because everybody wants 60 more people and, and no! Right? So, but then that forces the question of, well, then what’s the prioritization? And I will say I have, I’ve had two amazing bosses since I’ve been there. One hired me and she’s such a high flyer that after five months she became the CEO of Card and also the CEO of Connected Commerce. So, the biggest business and the most strategic business, which just gives you a sense for how freaking smart she is. So she’s lovely. And then my second boss used to be the chief technology officer, and now he’s in charge of product, design, data, et cetera. And and he has been fabulous because I said to him, look, one of the issues we’re running into is what is the prioritization? What is the prioritization across these lines of business? Because everybody thinks their stuff is most important. So he has been driving some really tough conversations about what actually is most important. Because we don’t have unlimited resources. Even if we have money, it doesn’t mean we have unlimited resources. And so again, like he’s been hugely helpful. And the amount– the amount of impact that had on me and the team was tremendous. And we also, you know, he’s also been incredibly helpful just to make sure that we are having every design leader that sits within a line of business sits at that CEO table, right? One design leader per, which is critical. And, though, I’ll tell you this, just ’cause you get a design leader up there, then they have to figure out how to act when they’re there. So there is someone I was hiring and you know, we were doing some feedback. I give everybody feedback after 90 days or. And some of the feedback was, Hey, you need to step up more and have a louder voice. And this person said, “Okay. Yeah. I mean, like I’ve always been fighting. We need to get at the table, but I’ve never actually been at the table. So like, so, so now that I’m there, I kinda don’t know what I’m doing.” And I’m like, that’s okay, well, figure it out together. Stop fighting, start partnering Peter: So many design leaders, and you’ve probably had this experience as well, you know, your posture is one of fighting, it’s fighting for your team. It’s fighting to be understood. It’s fighting for resources. It’s, there’s, there’s a kind of struggle that happens. And, but, when you get to be at this, what I think of as true executive level, if you come across as a fighter, you’re… That, that becomes a problem. Yeah. Kaaren: You are junior. If you come across as a fighter, if you’re not looking at the bigger team, if you’re not looking at the bigger business and if you’re not respecting, like, you know what? You are the best player in that role. So, you know, just let me know what you come to. I’m gonna run with it. I trust you. Peter: So, how do you, what is that coaching that you’re providing to help people kind of flip from that fighter mindset into… So I have the Patrick Lencioni book behind me and he talks about “the first team,” right? And, and to reflect like, as a design executive, your first team, isn’t your design org, it’s these other executives that you’re now partnered with. What have you done to help people kind of shift that thinking? Kaaren: Well, you know, it’s funny ’cause one of the things that I do deliberately is I’ll ask people, you know, who is it that you’re …whatever, whatever tool you use, right? So in our case we use Symphony, but great. Who are you Symphony-ing with the most, right? And if it’s not your product, eng, and data partner, then what are you doing? Right? Then you’re spending the wrong amount of time with them. And so I think that there are some little ways that you can reflect on how are you spending your time. I think the other bit is to figure out… what I realized is I often ask the exact same types of questions in every room that I’m in, and I’m asking those questions because usually other people are not, and they’re very important, right, to me. And I believe…

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31: Sustaining yourself as a design executive (ft. Katrina Alcorn, GM IBM Design) Aug 25, 2022

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Transcript Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, Together: And we’re finding our way… Peter: …navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show, What’s it like to lead design for IBM? Katrina Alcorn knows. She’ll share with us a bit of the view from the top of one of the world’s largest design organizations. We’ll also talk about the role of design leader as organizational change maker, how to keep reserving space for creativity and play and avoiding burnout along the way. Defining “Design Executive” Peter: Hi, Katrina. The reason Jesse and I wanted to talk to you is we’ve been thinking a lot about what it means to be a true, a true design executive. I think there’s a lot of design leaders who are being. Given executive-ish titles, but aren’t true executives. And so we’re interested in what it means to be a true design executive. And when we thought about who we knew who qualified, you were pretty much at the top of that call sheet. Looking at LinkedIn, your title is general manager of design at IBM. What is that role? And is it as grand as that title suggests it is? Katrina: I, I know everyone, no one’s ever heard of a general manager. You know, I work now for one of the biggest companies in the world and one of the oldest ones. So this, I think, I guess, was the title we had in the fifties and we have it at IBM, but it’s very meaningful. So, so the way maybe, maybe it helps if I explain a little about the hierarchy at our company. So the, the way we’re structured is obviously we have a CEO, Arvin, and then the CEO staff, you know, he has an operation staff and then he’s got these senior vice presidents. So there’s the SVP layer that, that run the different parts of the business: software, consulting. We have a huge consulting arm. Infrastructure. We still make mainframes. We’re now making this really cool thing called quantum computers. That’s an infrastructure. And so then so you’ve got the SVPs and then you have general managers and the general managers run the different business units. So I happen to, I have a weird role because I happen to sit in software, but I play two roles and I, it probably helps if I explain this, even though I, it doesn’t, it probably doesn’t apply to other companies. So my peers, where I sit in the company run, you know, multibillion dollar businesses in automation, in data and artificial intelligence in security software, things like that. I’m unique and special because I run design. So when I took the role, when I accepted the role last year, originally, it was positioned as general manager of design. There’s only one at IBM. It’s, you know, it was positioned to me as the most senior design role in the company, which it is, very exciting. And I was meant to basically be the steward for the design practice for IBM. So the design system, all the accessibility, tooling, all of the work we do around design career paths, which maybe we can get into. It’s very interesting and very well thought through at IBM. So that’s cross company, but right before I took the role, there was a little reorg and they moved all of the product design onto my team. So I find myself in this really interesting place where, on one hand, I’m sort of leading a, you know, a smallish team of about 70 folks who do this cross company, really what I think you mean when you say design executive, is how design is gonna work at this company, is about how design will help transform this company to be more innovative and be a leader in, in our field, in hybrid, cloud, and AI. But then I also have this job where I lead through authority because I have all of this software designers on my team. And so, that’s a different type of design executive where, you know, you’re, you’re kind of getting sometimes to get into the nitty gritty of the products and how, kind of, how, how are you optimizing design to ensure that we are making the progress we need to make specifically within our software business. So, so that was a lot of words in summary. I get confused sometimes by my two roles. One is leading design as a practice for the whole company and I have a team that does that. And then I have a much bigger team where we’re, we’re just actually doing the design work for all of software. And that’s about 700 designers. Peter: You, you mentioned you had peers, like literally, I’m assuming other general managers who are running multi-billion dollar businesses. Katrina: Yeah… Peter: And that leads me to wonder, what are you accountable for? Do you have a P and L? Are you, you know, how, how does that work? Katrina: You know, I’m still figuring that out, honestly. It’s— I am different. My role is different than the other GMs. You know, they’re, they are on the hook for P and L. They have to make money and they get to spend money. I have a, I have one budget for our design practice that, you know, is a, a fraction of my team, but the rest of the funding for our group comes from those other GMs. Funding models for Design Katrina: So I’ve talked with my peers at other companies because I haven’t decided if this is the right way. If this is the right funding model, I don’t think there’s one right funding model. So, so the pros and cons of how we do it now. I get funding from all the GMs to fund our, our designers. And, you know, we do a lot of puts and takes, and I have vice presidents of design representing those different businesses who are in the day-to-day on those leadership teams kind of negotiating. The good and bad of that is that when we get funding from the businesses to expand design it’s because they are bought in, they are a hundred percent invested in what we’re doing. The downside is it’s a lot of negotiation. it’s a lot of tin cupping. And it’s, you know, I… there’s a reason I’m no longer a documentary filmmaker. I don’t like doing fundraising so, you know, I, I don’t wanna be spending, I don’t think it’s the best use of, of me and, and my role. The flip side is, you know, the other extreme would be, there’s some kind of tax where we say “design is part of the cost of doing business.” And I haven’t figured out what that perfect formula would be, but I believe there, you could come up with a magic formula that says, you know, if design to development ratio is this, this is what the percentage of the budget should be. And as the businesses expand, design expands, and as they contract, design contracts, and then we are in charge of figuring out how to best deploy our design resources and work with the businesses on that. The downside is in my, my peers who run teams this way, they say the businesses, when they pay that tax, they feel like they paid. ” I paid for design.” So if there’s a need to invest more in design, it’s like, well, why should I do that? I already paid, I paid my tax. So as much as I don’t like fundraising, I– I’m really starting to value the, the hard work that goes into getting people on board with paying for design. Jesse: Katrina, how long have you been in this role at IBM? Katrina: A year, a, a year and a month. Yeah. Jesse: Yeah. Yeah. So 13 months into it, I’m curious about what that experience was like for you stepping into this situation, having this shift in your mandate, and then, obviously, getting to know a whole bunch of players very quickly, to be able to start having those conversations about budget and stuff. And I’m curious what that experience was like for you and how you approached getting to know a whole bunch of new people all at once and starting to build those bridges. The trajectory of design at IBM Katrina: Yeah, I, I did this massive listening tour when I took on the role. And so I joined IBM in July of last year. And there was a week where we were starting to open up from the pandemic, and suddenly planes were flying again and they had people on them. And this was right before the Delta variant hit. And so I spent my first week on the job in Austin, Texas. It’s probably the most exhausting week I’ve ever had because our flagship studio is in Austin. So we have designers all over the world, but we have the most designers concentrated in one place in Austin. And, the designers put on this incredible pageant for me, I, you know, all day long, I felt like I was sitting through one TED talk after another of all the amazing things that our design teams were doing around sustainability and artificial intelligence and, you know, really deep technical stuff and, and some really cool purpose-driven stuff. We have this racial equity in design program. So all just getting my head full of these things. And then I went back home and the Delta variant hit, and I didn’t see anyone for months and months and months. But I, it was very helpful, I think to get that infusion of facetime. I then spent the next few months doing a virtual listening tour where I think I did one-on-ones with more than a hundred people, not just in design, but of course our cross-functional partners and our senior executives around the company, just listening for: Where’s the opportunity? What, what are we doing well? And where is the room to improve? You know, what, what should my mandate be? And I should, at some point I should probably explain the trajectory we’ve been on. ‘Cause it’s really interesting. I mean, IBM had almost no design happening in the c— I mean, no designers in the company, 10 years ago, we had this rich history of design from the sixties, then that fell away, no designers. And then we had this new CEO 10 years ago, who said, let’s, let’s do this again. Design is gonna be the thing that, you know, helps us differentiate. And so Phil Gilbert was anointed as general manager and he built the practice from a few dozen people to 3000 and he built all the, you know, he and his team put all the foundation in place for design. So when I came in, Phil’s retiring, he brought me in. I’m listening for, okay, we, we did all these things, right? I mean, that’s what I saw. Like we hired the designers, we put them in all the right places throughout the whole business, not just in software. We had all these amazing programs running, but I’m also looking for, What’s not working, you know, where can we move the needle or where did we maybe take a wrong turn, where we can course-correct. And it took probably four or five months to really have a, a pretty clear informed point of view about that. And then I worked with my team on articulating that into a vision and that was a really fun and exciting process. So that was the first six months. And then the next six months was about socializing the vision and starting to put it into practice. And, and creating real programs and, and having real measurable, you know, goals around making these improvements. Peter: Can, can you share what this vision is? Is there a public face to it at least? Katrina: Yeah. Yeah. Well, I’ve been blogging about it actually, so, and I’ve never worked this way before, you know, in previous jobs. I don’t know. It was always more internal, but I think because the IBM Design program is so external-facing it’s, it’s really well known. And I decided to just start blogging about what I was learning and getting feedback both from our designers in the company, but also folks outside of design. So I’ll, I’ll try not to go into my total stump speech cause I’ve done this a hundred times, but here’s the big ideas. Okay. So we had almost no designers at the company 10 years ago. Phil Gilbert, who is a legend, the, the former GM, led this incredible revolution to reinvigorate design at IBM. And when he was recruiting me for the role, I asked him, “How are we doing? How are we doing with design?” And, you know, he told me about all the cool stuff. And I was like, “Yeah, but how are we really doing, how’s it transforming the business?” And he said, “Well, we have pockets of excellence, but we don’t yet have pervasive excellence.” And I, he said that, right, even before I took the job and it was, I had this ideas list of every time I talked with someone, I would like hear an idea between the lines and then I would capture on the list. And that was one of the first things I captured. And it was the thing I kept going back to because I really think that’s the job now for all of us is how do we take this incredible foundation that’s been laid, this investment and kind of supercharge it so that we’re scaling excellence that is happening pervasively across the company. After many, many, many conversations and roundtables and all the, all the things we do as designers to learn what, where we landed was on three areas. And I, in my head, I have a multi-year roadmap around these three areas, but we’re, we’re going agile. So , we’re taking ’em off one piece at a time. So the three areas are around customer insights. I think there is a lot of opportunity for us to do for, you know, user research, design research, what we’ve already done for the core discipline of design. So a lot of things happening there. The next area is around teams. And you know, you you’ve talked with other design leaders about this. I’ve listened to your podcast and we, we can’t be successful in design when it’s just design. To really, really be successful, you know, whether you believe in the statement of everyone as a designer, everyone has to care, they have to care about the people they’re serving and really be thinking critically about what that means. What can we do from our perch in design to ignite that and make sure we have strong cross-functional relationships. So there’s a whole body of work we’re doing around that. And then the last piece is around learning. And one of the things that is so exciting to me about this role at IBM is we operate at scale. So, you know, Peter, when you and I first met 20 years ago you all were running Adaptive Path. I was working at a rival agency that was about the same size. You know, we, neither of us had more than a hundred employees, and designer education for us then was you send your designer to a conference once a year or, or you sent them to go speak at one, and then you don’t have to pay for it. That was pretty much the extent of it. So now, you know, we’ve got 3000 designers and they’re actually thought leaders in the type of, you know, work that IBM is trying to do around things like artificial intelligence. So we’re really trying to unlock that learning to create this, these kind of training programs inside our company to kind of harness that knowledge and help our developers or help our designers kind of grow from each other. Where to focus time, effort, and energy Peter: I’m wondering, particularly in these last six months, and as you look forward to maybe your next year, one of the questions that I get a lot, one of, one of the challenges that I think a lot of design executives have is knowing where, and how, and with whom to spend their time, because time is a finite resource. Time is the only finite resource. And it would be very easy for someone in your position to just work 120 hours a week, because there’s enough stuff to do that you could do that, but I, you, you would burn out you’ve in fact, written a book about burning out. We can get into that. You have a life outside of work. You recognize the value, even if you weren’t a working parent, even if you weren’t any of those things, you would also just recognize, like, there’s a, there’s a, there’s a point at which you, you just can’t give anymore and it’s not healthy to, to keep working. So what have you, particularly now that you’re operating at this even newer scale, right? Your last job at Autodesk, you probably had a couple hundred people in your team. Now you’ve got 700 that you’re kind of directly responsible for in another 3000 that you’re somehow responsible for. , how are you, how are you figuring out where to focus your effort and energy? Katrina: Yeah. It, well, first of all, yes, we,…

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30— Mailbag: UX maturity, conflict fatigue, and getting past imposter syndrome May 25, 2022

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Transcript Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, And we’re finding our way Peter: navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show, Peter and I take a break from interviewing guests to ask each other some questions and answer a few of yours as well. Along the way we get into topics like organizational maturity, career trajectories, the role of diplomacy and leadership and connecting leaders to their true sense of purpose. That’s right. It’s time for the mailbag. Peter: Hey, Jesse. So today I thought we do something a little different. Instead of a conversation with a friend of ours, have you and I converse. I think it’s, you know, it’s been a little while since you and I have had an opportunity just to chat. We didn’t want to do this in a, as… a navel-gazing fashion. So we’ve, we’ve elicited questions from the community through various channels: LinkedIn, Twitter, and email. And we have some questions that we’ll get to, but I, taking my co-host prerogative, do want to ask the first question and it’s a question of you. And it’s… I realized, I don’t know, kind of where… what your perspective is right now on matters of design and design leadership. Like what, what your point of view is. And I’m curious what patterns have emerged in the conversations you’re having with design leaders in your coaching practice. Improving UX maturity in an organization Jesse: So for those of you who don’t know I’ve been away from my leadership coaching practice for a bit as I’ve been dealing with some health issues. Last year I was in treatment for cancer all year long, but I’m happy to say that I’m feeling much better and I’m back at it now. And so I’ve been back into the swing of coaching for the last few months, and it’s been interesting to return to it with this perspective, having taken a year off and noticing the conversations that I’m having with folks now. And you know, one of the interesting themes over and over again, that’s coming up in my coaching conversations, revolves around something that you I’m sure have a strong perspective on, Peter, which is organizational maturity. What I’m finding is that a lot of these leaders, the biggest struggles that they have are the fact that they are embedded within organizations that are not as mature in their UX practices, as these leaders feel they need to be in order for them in their teams to be successful. So over and over again, what I’m seeing is the main question that these leaders are dealing with is the question of, do I stick it out here and try to push this organization toward a level of maturity where it can deliver on the promise and potential of design? Or do I cut my losses, get out, and go find another organization that’s already operating at that level of maturity? And it’s a difficult thing for individuals to find their way through because that task of pushing the maturity of the organization forwar,. It asks something very different of you than simply jumping in and operating in a, in an… in a situation where you were already sort of set up for success. Peter: A clarifying question: when you’re talking about maturity, are you talking about maturity of the UX organization, the UX team, or are you talking about maturity of the broader organization to embrace user experience or…? Jesse: It’s the well, it’s mostly the the maturity of the broader organization. Although I will note that along the lines of our conversation with Tim Kieschnick, the maturity of the larger organization ends up strongly influencing how mature your UX team can. Peter: Right, right. And so. That’s interesting. I mean, this… I’m reminded of when I joined Groupon 10 years ago and there was a lot of interest in being design-driven. And so if we use the leadership ceiling kind of framing, there was actually a pretty high purpose ceiling in, in that regard. And, but when I, so I inherited a team and what I saw was that, that it was the team that was immature much more than the broader organization. Not that the broader organization was all that mature, but it didn’t matter how mature or immature the broader organization was because the team was evidently immature. And that’s actually what led to writing the book, was this realization that we need to first mature our design organizations before we can then start trying to mature design within the broader organization. And I’m wondering if you’re, if, if that is a pattern you’re seeing. Whether or not these design leaders, you don’t, I, you know, I, I guess, I guess it might be hard for you to diagnose just how mature somebody’s design organization is. But let me, let me just say that I’ve seen too often design leaders, rail…they get frustrated by what they feel is the immaturity and the constraints the broader organization is putting on them, but they don’t accept responsibility for the fact that their organization isn’t, isn’t even measuring up to the ceiling that that broader organization is, is affording. That they’re not doing that initial work… Jesse: right. Peter: …to mature their teams. Jesse: Right, right, right. Well, and. It becomes a question of what kind of maturity you’re talking about because there is a level of maturity of team structure, of process, of governance that are the kinds of things that I think you’re exactly right, that if a UX team isn’t, it doesn’t have that stuff in place, there’s no point in asking for a broader mandate because you haven’t demonstrated that you can deliver value at that scale yet. But the, I think the, the kind of maturity that these leaders are running up against that I’m hearing about has to do with a maturity of understanding of expectations, of design, of appreciation of the value of design that they’re seeing doesn’t really exist in these organizations around them, or doesn’t exist at the level that allows them to really do what they feel like they’re there to do. Peter: And that pain is real and I see it all the time. And, and Yeah, so then it becomes this question of, it’s funny, a lot of this is going back to our conversation with Tim, you know, you’re, you’re, you’re going to operate below the organization’s maturity ceiling. And so as he pointed out, you have kind of two options. You can bide your time or you can bail. And that’s, that’s individual to the person in terms of what, what, what path they choose based on what else is happening in their relationship to that organization? I say, I think primarily around their commitment to the mission or purpose of that organization. And if it’s an organization that they feel strongly committed to and they want it to succeed, then I would say, and then it’s your job to, then, as Tim pointed out with the letter C, change the ceiling and that’s, as he said, it’s not for the faint of heart, but this is the real work of design leadership. And I think one of those things, that when people ask why, how, is being a VP of design different than being a VP of marketing, it’s– it’s this immaturity question, companies are mature much more mature in thinking about marketing, thinking about engineering, thinking about sales. And so your VP doesn’t need to keep evangelizing and educating everybody as to what it means to do it, right? Companies are immature about thinking about design. So part of the job of that design leader is education and evangelism. That’s just… that’s… that, you can’t get away from that. I mean, the last thing I’ll say is, on at least in this front, is I have been surprised… so I’m, I’m currently supporting an organization where this type of maturity, in- increasing the maturity is, is, is a goal that the design team has. And so they’re having to communicate how design works to a broader, primarily product, organization. And this is a big company. These are, you know, billions of dollars; very senior leaders. And what surprises me is how rudimentary the conversation is that the design leaders are having with the broader organization to educate them. I mean, I’m working with design leaders with 25 years experience who are rolling out the double diamond at its most basic to communicate, This is what design is, and who are leaning on the DMI index of how design-centered companies do better in the stock market, like reports from 5, 10, 15 years ago. Jesse: These are old tools that have been used for a long time to evangelize design. Peter: And they’re still working and they’re still working. And so I think one of the things that we have to recognize as design leaders, who, because we’re experts in it and might think that this stuff is not all that valuable, they’re not all that useful or, or too basic. What’s basic to us is mind- expanding to others and, and to not shy away from, from returning to those rudiments in, in starting that process of maturing the organization. Because if you’re trying to meet them at your level of maturity, they’re not going to get there. They’re not going to get there. The delta is too big. So you have to kind of get to where they are at their level of maturity and then grow them. The reality of conflict fatigue Jesse: I wonder about the psychological toll on leaders of taking on this role that you described, where you are inevitably, constantly putting yourself in situations where you have to su—… you have to have arguments with, you know, you, ….changing people’s minds means getting them to let go of their old ideas. And that is hard work. It’s difficult work. It is also, it means plunging yourself into conflict over and over and over again. And it’s this conflict fatigue that I see setting in with design leaders that they’re just like, it sounds like the way that you’re describing it, taking this job means signing up to be sort of a crusading holy warrior. And not everybody who wants to run a design team wants that mantle put upon themselves, you know? Peter: I think so. So yes. And a couple of thoughts in this design team I’m supporting, they’re hiring amazing design leaders from other organizations. Design leaders… so, so this, this team has 500 some designers on the way to 700, by the end of the year. It’s just, I’m saying that to reflect on scale. And they’re bringing in design leaders who are leading teams at other companies of say 500. And…but bringing them in to lead a team of 50, a 100, 150. And it’s because those leaders are done fighting that holy war. And they want to be part of an organization where someone else is above them. Who’s waging… waging those battles as it were and they get to focus on the work. And so that’s a decision for design leaders is do… I’ve… I’ve had in my conversations with, with the leaders I work with, there’s another one in particular, he was a head of design for one company, 40-ish person team, moved, became a head of design at another company, 50ish person team. Both of them, there was this jockeying and evangelizing, educating. He was actually really good at education. He was really strong at connecting business value with UX metrics. And so his leadership tend to really like him, but the, the, the, the, the more recent company he had been working for, they had their fortunes turn a bit and the job changed. And he’s like this isn’t the job that I signed up for. And he realized, “You know what? I don’t want to be the guy. I don’t want to be the guy. I want to be a guy.” And so he found a job at a ginormous tech company to run a team that’s the same size, maybe even larger than what he ran before, but in such a bigger context that he’s, he doesn’t have to wage those battles and fight those fights. Playing politics instead of fighting battles Peter: ‘Cause he just doesn’t have the energy for it. So that’s one thought. The second thought is there’s probably, there’s more than one way to skin a cat. And I think leaders, and I’m wondering, kind of, in the conversations you have, the strategies you’re developing for these leaders in terms of figuring out how to address that, does it have to be waging a holy war or can it be more political? Is there a Realpolitik approach to this? And I think about this in light of, one of the things I did in this past year was watched The Wire. I’d never watched The Wire before. And the first season of The Wire is filled wiith grist for leadership conversations. In particular, Lieutenant Daniels ,I’m spacing on the actor’s name, Lance Reddick, Lance Reddick, the bald one who’s kind of running the group. And there’s an amazing scene, I forget which episode, where he’s, he’s got his kind of gang of misfits that are, they’re trying to, he’s trying to stand up this group to do this investigation and he needs something from somebody and it shows him very slowly and purposefully escalating his ladder, to his leader, talking to his leader’s leader, all the kind of background stuff that needs to happen in order for him to secure the resources that his team needs in order to succeed, that his team doesn’t realize he’s doing, right? This is that thankless work that design– that leaders do ,not just design leaders. But he’s not fighting. It’s not conflict. It’s politics. It’s, it’s diplomacy. It’s, What do you want that I can provide in exchange for what you have that I want? And it’s, and it’s, and it’s working a system. Now, that’s also tiring, but it doesn’t have to be as conflict-driven as perhaps more just like, more, you know, in the context of designing leaders, it’s like, okay, I don’t want to fight about it. I don’t want to argue about it. I just, I want the thing I want. So what do you need from me, so that you’ll give me the thing I want and just trust me that the thing I want is right for all of us? And I’m wondering if there’s a strategy there that design leaders could be employing more. I think we seek education and evangelism as the one tool we have to influence an organization, and don’t recognize there’s other means of influencing the organization. And then when we get what we want, by whatever means, and our team does great work, then we can evangelize and educate. I think we try to do too much ahead of the output, and instead don’t rely, don’t, don’t use the good work that the team is doing to then get what we kind of want further down the chain. Why does design leadership always feel like a fight? Jesse: I like the metaphor of diplomacy. I like the idea of engaging in this conversation from a place of, we’re going to sit down at a table as equals and talk about how we work together toward the common good. You know, one of the questions that we got in the mailbag was this question from Dimitris Niavis on LinkedIn. “If you had magic and a time machine, what would you do differently as a design leader?” And honestly, this thing for me, as I reflect on my career, I think that this framing of our work as a fight is something that I have indulged in much too much over the years that I, as a consultant, engaged with our clients with an eye toward who’s on your side in the organization, who’s not on your side in the organization. What are the, what are our tactics for you know, winning those battles. And I don’t think I encourage my clients to take enough of a diplomatic approach to these things. I did see it as a battle to be won, and I don’t think that that served the work. And I think that a lot of people throughout the industry have taken on that framing. And I don’t think it’s serving them as creative professionals either to be constantly on the lookout for enemies and not to engage people from a position of mutual trust and good will. Peter: And, and, kind of, common, common goals. And I I’ve been guilty of similar stuff and I, and, and I still am, I suppose, in that I teach, when I teach my design leadership workshop, I use this framing of the four archetypes, the coach managing down, the diplomat managing across and the champion managing up . And the champion, is, I’m drawing upon kind of medieval, if not earlier, right, kind of models of the champi…

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29: Listening with Intent (ft. Indi Young) May 14, 2022

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Transcript [This transcript lacks the polish of some of our others. Please forgive!] Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, And we’re finding our way Peter: navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show, Adaptive Path co-founder and author of the forthcoming book, Time to Listen, Indi Young joins us. She’ll share some of what she’s learned from her career, giving organizations tools for empathy with their users and individuals, the skills to listen deeply to each other. Origins of Indi’s methods Peter: Hi, and welcome to the podcast. So I, we’re just going to dive right in. We’ve known you, we’ve known each other for well, over 20 years. We started Adaptive Path together. I knew you, I think, through the Miller Freeman web conferences even before then. And I’d love…. So we, when we were working together at Adaptive Path early on, you introduced me to your pro… process, in particular the mental model process, and then you ended up writing a book on mental models, and then you’ve written a book on practical empathy. And now you’ve about to, and you can tell us kind of the details, release a book called Time to Listen. And this is a big question and take as much time as you want answering it. But I’m curious about this trajectory that you were on and how you’ve seen kind of your progress or your evolution from when we first started working together, building mental model diagrams, to kind of your, where, where your head is today in, in, in how you approach your work. Indi: I could take like the whole hour answering that one question, Peter: Well, Indi: you guys will, but, but in with other clarifications yeah, the and yeah, I, I was trying to think back, like how, how did we meet? And I only remember meeting Mike from Adaptive Path on the ski lift at Sugar Bowl. So I can’t remember all the other origins story, but anyway trajectory, I started off, trying to embrace and adapt the the business, or rather the engineering approach of writing functional specs. This was long, long, long ago, Jesse had written, he, he wrote that book. Uh, What was the one? I can’t remember the title of it. It has Jesse: My book, you’re talking about my book. Yeah. Indi: yeah. Your book. Yeah. And that that’s it. Yes, the layers one. Peter: right. Indi: But that came out like after I had given up on the func spec and it reminded me a lot of the func spec, the functional spec is just kind of like writing out everything that the thing has to do. And that is very much about understanding how a process works, how a standard operating procedure works. And, and in coding it and how do we encode it? And then, you know, w- how do we make an interface on it? And so that was very much about processes, methods, procedures, all of these things have different contexts, where there are edge cases where like, okay, in this context, the method doesn’t work quite this way. This is how it is done, or how other people have done workarounds. And so we need to encode those work arounds or those other contexts, and those are called edge cases. And what was happening when we started Adaptive Path was that we were no longer focusing only on engineering and science as things to encode or business processes to encode. Right. We, we were starting to encode things that had more of more of a service aspect to it. We, what did we do? The NPR site or something, right. Peter: NPR, PeopleSoft. Yeah. Indi: Yeah. W- it was not a process. I mean, sure. Sell PeopleSoft. We were working with a sales group and sales could sort of be said to have a process, but it’s the closest thing to listening deeply, actually. So So we were w- w- that shift had happened. And along with it, we pull a little bit of the functional spec with us. And we also pulled that word edge case. And the edge case was now a word that was applied to people. And this is where I started going, like, okay, there’s friction there. That’s not right. So that was my personal response. And because you don’t call a person an edge case, no person is an edge case. No human mind is an edge case. There are communities and groups and ways of thinking. Yes, but nobody’s an edge case. The edge case belongs to the process. Anyway that was my personal sort of issue with it. And the rest, the rest of the evolution is really all about me learning from the people who are working with me, or me learning from the people who are learning from me about how. How to, how to make a clear guide, a clear method you might say for working at understanding people’s minds so that we can create support for different thinking styles for different approaches to the same purpose. Evolving mental models Peter: How so, you know, in 2001, we worked together building mental models, right? You’re, you, you talk to folks, you listen deeply, you take a lot of notes and then you kind of decompose and recompose what you heard to create these structures that help you better understand how folks think about how they solve problems and then also go about solving those problems. Right? There’s almost that it’s almost kind of two layers to it and you call it that mental model diagrams, a book about that. I’m curious because that’s where you and I kind of diverge is, is you, you know, you left Adaptive Path and continued to develop your practice. And you’re mentioning how you developed it in response to collaborating with I’m guessing people within various organizations. I’m wondering if you’ve had kind of, if you have a stories to tell of kind of a clear aha moment where you thought things should be one way or behaved one way or where you used to practice one way, and then based on an experience you had in collaborating with someone you’re like, oh, wait a moment. This is, I have a better idea of a better way of approaching it, given this kind of experience I’m having. How, how has, what were some of those steps… step changes been. Indi: The there, yeah, there were a lot of step changes. Probably too many for us to cover or from even to remember what his step changes was that aspect of taking notes, lots of notes. I, when I started trying to teach her, I think our team members at adaptive path, right, how to do this, it’s like, Ooh, paying attention to what a person is saying and, and writing things down about what they were saying. I’m a light, just let it be a transcript. It has to be a transcript cause otherwise you’re going to be doing too much thinking and not hearing. And, and and this happened even after I, I left Adaptive Path as that people would want to write notes and they would say writing notes is how I make sense of the state is writing notes is helping me analyze this data so I can come away with insights. And that was a huge aha moment for me because, and of course this is layered. First of all, I don’t want the insights to happen while you’re listening to someone. When you’re listening to someone, you have to pay rapt attention and that’s it. You’re going to follow that person. And that’s it. You’re not going to bring up topics. You’re only going to follow their topics. The thing that you do as sort of a background process in your own mind is making sure that they are getting to their interior cognition and helping them there, or helping them clarify points that their interior cognition for each topic. So there’s a lot to unpack here. So the first aha moment was okay, no notes. This is at the time you know, we, we would sometimes be bringing recording devices in. We would sometimes be doing this by conference call and sometimes just doing video recordings or whatever. Right. But we’re recording, so we’re not taking notes. And that was a huge, aha. I think that really helped people understand that in a listening session, it’s not, it’s not where you’re trying to forge insights. You not trying to do your work there. Your work happens later. What you’re trying to do in a listening session is understand another person’s perspective, another person’s approach to the purpose, another person’s, you know, if you’re not spending that time, understanding them, you’re not going to get their perspective. What insights you’re going to pull out of this are going to be your own insights. Not understanding someone else’s way of thinking. And this is why we continue to have software and services that, that don’t support anyone. That’s very different thinker than the team themselves, because we automatically, we feel like if we’re going into a listening session, we have to work. We have to do some thinking and come out of it with insights. And in, in, if we’re going to understand somebody else’s way of approaching this purpose, what we have to do is let go of… we are not an employee at that point. And so this was an early on thing I would say, you’re not an employee, you’re just a person you’re just listening. And then later on, I ki– you know, and no notes, right? You can, if you think they’re bringing up a topic that they may want to unpack later, and you both may forget about it, you can jot down that topic, but that’s all, you’re not going to write notes. And then later what happened was this idea that the rapt attention and the following and the topics really help people or give them sort of a guideline for paying attention to the other person. Being able to recognize that you’re not allowed to bring up a topic. You’re not going to bring a question into this that you invented outside of that. You’re only going to be asking people about their interior cognition, their inner thinking which includes, you know, all sorts of inner thinking, their emotional reactions and their guiding principles, which are kind of the rules that they use to make decisions or how to act or react. Types of empathy Indi: So so those are the interior cognition things and that’s so I was sitting at breakfast with Lou Rosenfeld. I really wanted to write this next book. We were, it was like a perfect day and we were at this restaurant that was on the water and there were sailboats going by and we’re both like, oh my gosh, this is like, how did we end up here? It was beautiful. And so I’m trying to explain to him what this is. And he finally goes, he says, well, so what you’re talking about is kind of a practical empathy, right. And um, Okay, that works. And that’s when and so, and then he finally agreed to let me write the book. And and that’s when I started researching, well, what is it the mean anyway? Cause like the way people use it as varied and it turns out that there’s so many different types of empathy in the psychology world and they’re all totally valid. And there are books written by particular professors of Yale um, who um, who take one definition of empathy, which is the def– the type of empathy called emotional contagion. And then they’re all like I’m against empathy. And and the kind of empathy. I meant that when I’m paying rapt attention, what I’m trying to do is get my head inside their mind and understand their perspective and see their perspective. And that kind of empathy is called cognitive empathy. It’s just a different kind of empathy. There’s a third kind of type of empathy that this very popular, Dr. Brene Brown speaks about it. And that is what the psychologists call empathic listening. So it’s an in the moment, empathy, cognitive empathy is building an understanding of somebody. It can, it can happen over time trying to get their way of thinking their interior cognition and empathic listening is noticing something’s going on for some. And it’s normally introduced as an emotion going on for someone normally a negative emotion going on, but it can be anything, it could be interior cognition, which includes inner thinking. It can includes like a, a pause, like so normally my guiding principles to do this. And normally I would decide that, and you know, you’re not thinking that consciously, but you’re pausing. And if you notice somebody pausing or you notice somebody having something going on, then what you can do is offered, listen, and that’s called empathic listening. And so in the moment, what happens is that the end of it, the other person feels heard and maybe their pause or the something going on is a little easier for them to deal with. But that’s a, in the moment thing, whereas cognitive empathy is long-term thing. It, it gathers information for us to be able to understand what those groups and communities of thinking are so that we can start writing support. services for those different communities of thinking. And those are what I call thinking styles. So there’s another, there’s another a day. But I tell you about when Christina was talking to me about thinking styles, but um, Peter: Christina Wodtke Indi: yeah. Do you want to insert anything first? Peter: uh, Jesse, Jesse looks like he’s got a Jesse: I, I am going to change direction here a tiny bit. Seeking the intangibles Jesse: I curious about this turn that you described in your thinking and not just in your thinking, but I think in the thinking of a lot of people at that same time, from a process oriented approach, to thinking about how we structure the requirements that will ultimately drive design decisions toward an approach that looks at more of the intangibles, right? Less of the things that you can measure with a stopwatch in the old fashioned industrial style And ended up curious about what you went through in bringing organizations around to this kind of thinking as someone who was working most of the time as an independent consultant, just one person coming into an organization as you have over and over again, over the years, and helping people see a different way of doing things. And and I wonder what you learned about about helping to create that shift of mindset inside organizations over the years. Indi: THat’s a really good question. That’s the thing that I have had the hardest time with because I’m I’m naturally an introvert, so I’m like, I don’t want to get in other people’s business, you know, they can do things the way they do, but I was so on fire about this and I actually caught fire. Stronger after we have sort of this populist political scenario happening in the mid 2010s. So the, the fire pushed me past being an introvert. Um, And I utterly did, I, I’m not naturally gonna go there, but, but this had to be done because, and I did not do it well, I didn’t know how to do it. I still am struggling to do it, but I’m getting a lot better at it, which is taking this idea. So I’ll, I’ll, I’ll sort of lay it out as a, before and after, before what would happen is that the. Methodological-ness of it. The, the way that a an opportunity map, which is another change that we did looks, it’s a mental model diagram on top with the capabilities aligned beneath, it looks like a city skyline in that that sort of like solidity attracted people to to this approach because you’re right. We’re trying to, we’re trying to understand the intangibles and having a tangible method for doing that was really reassuring, Jesse: so you think it was the visualization itself that helped make it feel real? Indi: yes. I think it was. And then my confidence in being able to build that visualization based on cognitive empathy. So to, to make that intangible, tangible, I think is what made people reach out in the beginning. And so for many, many years, that’s all I was doing was I was relying on an individual to get interested in the way of looking at it, that city skyline kind of thing, and interested in how it is built and then to hire me to build it. And I would do that. And then I would work with them with the, with what we’ve got, okay, what are we going to do with this? How are we going to approach it? How are we going to find you know, a solution? And in the beginning I knew these things would last for decades and it wasn’t about a solution. It was about many solutions, but it was very hard to convince people…

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28: The Leadership Ceiling (ft. Tim Kieschnick) Apr 29, 2022

Show notes

Transcript Tim: So the first piece is to align around the shared purpose and you cannot have any successful change of any kind if you don’t have something about shared purpose. Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, Together: And we’re finding our way… Peter: navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show, recently retired design leader Tim Kieschnick offers insights from his 30 year career in design and innovation at the health care giant Kaiser Permanente. He also shares with us his insights into the ways leaders hold back their teams through a model he calls The Leadership Ceiling, and what to do about it. Introduction to Tim Kieschnick Peter: So hi Tim, hi Jesse. Tim Kieschnick is someone I worked with for about a year, when I was supporting Kaiser Permanente a few years ago and he brought me into his team. And what I, I, I learned a lot from just that year that I spent working with Tim, Tim had worked at Kaiser for 30 years, he can correct me with anything that I’m wrong with in, in what I’m about to say, he worked at Kaiser for 30 years, helped establish their website, kp.org, their UX practice 25 years ago. And then when I was working with him was focused on this kind of combination of service design work to help the business think about omni-channel, cross-channel more strategic design challenges, as well as a human-centered design kind of workshop, facilitation, think Google Design sprint-type style work with different parts of the business. And so, he and I, over lunches and coffees had a lot of conversations about design, design practice, leadership. And so I wanted to have him on the show and in particular, and we’ll, we’ll dive into this soon, he has this concept that he calls The Leadership Ceiling, and it’s a framework and I love frameworks. And so we’re, we’re going to have him unpack his framework for thinking about how leadership works. So thank you, Tim, for joining us. Anything I miss, any, any high points about your time at Kaiser or outside Kaiser as a designer and design leader that we should know about? Tim: Oh, no, that that’s pretty good in terms of the, the Kaiser years. I’ve– I would just augment it to say that, to me, design, human-centered design, et cetera, all of these methodologies for getting good things done quickly and well, and at scale, really go beyond any particular job or contexts. So I feel like I was doing design work before I knew it was design work. And I feel like, you know, now that I’m retired, you know, banging around my house with hammer and screwdriver, I feel like I’m doing a, I’m doing design, I’m doing human-centered design. I’m doing agile. I’m doing all of that in my everyday life too. So I’m very much a design-your-life kind of person and approach everything as a design problem because you’re, you’re more likely to come out with a decent outcome faster. “Everyone is a Designer” Peter: I actually want to dig into that a little bit. One of the controversies within the UX design field is this phrase, “everyone is a designer.” A lot of people with the title Designer feel that commoditizes or minimizes their work and impact. If anyone can do it, why do you need to hire people with degrees in it and all that kind of stuff? And I just wonder, again, given your, the arc of your career at Kaiser, you probably saw a lot of different shades of this, and your take on this controversy such as it is, is everyone a designer? Are some designers designer-er than others? Like how, how should, how, how did you end up thinking about it? Tim: Oh gosh, everyone is not a designer. Unfortunately. The first thing is that if design is limited to the people who graduated from RISD with a degree in design, then we’re going to have a whole bunch of unsolved design problems. There aren’t enough professional designers to address the number of design problems that we have. You just, we have to have people using the principles and some of the methods of design all over the place up, you know, just up and down the board. So there’s absolutely a place for the pros and the people who have formal training and the people who have experience and the people who geek out about this over several shots of espresso. There’s absolutely a place for that. But as soon as we start to confine it to them, we’ve just really, really limited the ability of the world to solve the problems that we need. So I feel really strongly about that. It’s, it’s, you know what, let’s use those professional designers very strategically when really when we need them, but let’s get as many other people familiar with the, the mindsets and the methods of design as possible. You know, for one thing, it’s, it’s a lot easier to work if I’m a professional designer, which I’m not, it’s going to be a lot easier for me to work with, with people who are not professional designers, if they have some sense of the mindset and some sense of the methods. Okay. So that’s the first thing it’s good for, for people to have, you know, have the, some of the mindset and methodologies, but then the other piece is just, I want everybody approaching problem solving in, in creative and methodical ways that, that explore the possibilities and that pay attention to the, the really the underlying needs and all that kind of stuff. And it… I’ve, I’ve, I’ve, I’ve got a real chip on my shoulder for a prima donna designers who don’t want other people to talk about design, don’t want other people to try to do it, because really this is me, you know, it’s like I’m saying, you know, really, you know, professional musicians are the ones who know what they’re doing. You know, we don’t want, we don’t want these amateurs around here, you know, strumming their guitar and singing “Blowing with the Wind.” And I think we really, really want as many amateur musicians as possible, you know? I’m… we were talking just before we started recording about how I retired a year and a half ago, and I haven’t been in the business world except in my interactions with bureaucracies in Vermont, which… bureaucracies in Vermont is a really new thing for me. It’s great by the way, the bureaucracies in Vermont all have people attached to them. It’s just amazing. They’ve got these really nice people who pick up the phone and know my name after I’ve called them once before. It’s, it’s, it’s a really amazing thing. They don’t have any computers. But they have telephones, and they have people, but anyway, so I’m banging around…. Yes. So I’m banging around my house and banging around the yard and, you know, I’m, I’m planting stuff in, in, in my yard. I am not a professional landscape designer. I’m not a professional gardener. I’m really glad there are people who can do that. But if we have to leave that stuff to the professional landscapers and professional gardens, we’re going to have most of the, most of the, you know, yards and gardens in the world are going to be crap. And that’s kind of the way we are with experiences that, that companies, that software development, you know, the, that we provide, is most of them are crap because there aren’t enough designers to come in and the people who are there just don’t have enough clues. So I, I, I’ve got a real chip on my shoulder about that. And I think as many people as possible who have some sense of this, the better. Jesse: I’m curious about your experiences over the course of 30 years with the same organization, having these kinds of conversations with people about design, about its impact, about its influence, about how you bring people into those processes and how those conversations changed for you over the course of those 30 years? How was it different by the time you got out than it was when you started having these conversations about design and what it can do for organizations? Tim: Oh, that’s– it’s a lot in there. One of the pieces is that some important changes happen really fast and a lot of important changes take a long, long time. And the ones that happen really fast, sometimes it didn’t happen as fast as it seemed like they did. We just don’t, we don’t hear about them until, boom, this thing gets implemented and you don’t see all of the slow stuff that built up to that. And so I’ve, I found it really, I don’t know if rewarding is quite the- quite the word, but meaningful to stick with something for a long, long, long time. And I know it’s, it’s, you know, it’s out of fashion, I’m a dinosaur, there’ll be nobody who works for the same company for 30 years ever, again, much less, 50 years. And we don’t even use gold watches anymore. But there’s something about having a long-term intent and sticking with it throughout. And then the, the key to sticking it with throughout is, as you’re saying, Jesse is, is to be able to morph as I go so that I’m not in, you know, 2022, fighting the 1992 battles. And that’s really, that’s really interesting, but I really– it’s interesting, very interesting to, and, and rewarding to see, to take the long view and to see where we are now, relative to where we were, whether it’s with, you know, a corporation or whether it’s with you know, the you know, w- w- with the country or anything that has, you know, that has the stamina, the staying power to last long. And one of the big things about that is this, this interplay between culture and leadership. So you see, and, you know, culture of course is more permanent than leadership and harder to change, but they’re, they’re very, very interrelated. And some of that led to, you know, my, my thinking about the leadership ceiling, which we’ll talk, talk about, I’m sure. As you see the leaders, not just the, the, the people in positions of leadership changing, but as you also see the individuals changing and morphing over time, to be able to adapt to that, to be able to fight, to be able to be very intentional about choosing, Which battle am I working on right now? You know, which, which aspect of the culture am I working on and who am I working that with? So when just before, Peter, you joined us, we had made a very– my small team had made, made a very intentional choice about which part of the organization to focus on. And it was interesting because, you know, we were trying to change the culture, to move the culture, to be more human-centric and more innovative and more designing and et cetera, et cetera. And we didn’t go to the most high profile or the mo- the biggest bang for the buck. We went to the place that we thought would give us the best shot at creating the germ that would grow into the, into the large crop. And, and so it’s always again picking, you know, which, which piece are we going after at any time and being really intentional about that? The other thing I want to say about that though, is, is in, in terms of the culture and there’s this theme at Kaiser Permanente around organizational structure, that is always the thing that is the best and the worst. The best and the worst of Kaiser Permanente all come from its organizational structure. And so whether you are inheriting an organizational structure or you’re creating an organizational structure, it’s critical that you understand what is embodied in that structure. So Kaiser, Kaiser has th- this you know, really interesting organizational structure that most people don’t know about and that they shouldn’t have to know about. But you have the physician, and the physicians, you’ve got primary care and you’ve got specialty care and then they’re all, you’ve got inpatient and outpatient physicians there. They’re all in, you know, like in a single physician group more or less. And then you’ve got the hospitals and then you’ve got the health plan, you know, sort of the the insurance side of the business and all of those three things come together and they include the pharmacies and they include the labs and they include the hospitals and they include the radiology of all of these different pieces that all have the potential to be integrated. And because of that, you can do things you can’t do other places because of that integration. And because of that, the incentives of the organization are fundamentally aligned with the incentives of the patient. So it’s fundamentally for, for decades, it’s been in the Kaiser’s best interest as an organization to do what’s best for the patient. Because of the organizational structure. And there are other places where the organizational structure is clearly set up, that what’s best for the organization is not necessarily best for the customer. And so how do you, how do you, you know, bake intentionality into the org structure. And Peter and I have talked about that a lot is, you know, how, how do you know it? You know, part of it is the hierarchies and part of it is, you know, anything from the metrics to the physical plant, to whatever it is, but how do you, how do you systematize intentions? it’s just a fabulously interesting area. The Leadership Ceiling Peter: Well, we’ll see how, how, how we impact that. We’ve been alluding to the leadership ceiling and I feel that we should unpack that now. So the leadership ceiling, Tim, I’ll let you define it, but just kind of i- it’s, it’s a tool. Here’s, here’s my little tease. It’s a tool that you’ve not really shared with the world. I’ve seen, you know, early writings about it. And I use it one-on-one with, you know, some of the design leaders I work with to help them think through their challenges. I found it remarkably valuable. So yeah. What is it, do you have a, you know, the, the elevator pitch on the leadership ceiling, and I’d also be curious, like how you arrived at it. What, what was it that got you to realize this framework? Tim: Okay. I’ll, I’ll start with the last question. So this, like many of my stories that goes back, goes back quite a while. So it, my, my son is 23 now, 23 years old. So– when he was four or five years old, my wife and I were shopping for where’s he going to go to elementary school? You know, you’re going to go to the local public school, there are a number of private schools. So we did some shopping around. We found a private school that we liked almost everything about. For one thing it was cheaper than any of the other private, private schools around. We loved the teachers. We liked that the building was great. They had a fabulous approach to an integrated curriculum, that a great afterschool program that supported people who were, you know, we had two working parents, et cetera. Just loved that,almost everything about the school, but we hated the principal. The principal was really problematic. So I called my dad because my dad was in schools and he was, he was a teacher and a principal and a school superintendent. He was, he coached principals. He was in schools his whole life, his whole career. And I said, you know, “Dad, how important really is the principal? You know, my kid may never even interact with the principal. My kid’s going to be with the teachers.” And dad, he didn’t, he didn’t skip a beat. He said a school can never rise above its principal. So we ignored his advice. He was basically saying, no, you know, if you don’t like the principal that it; we ignored him, we went to that school. And the short answer is by the time our son was in seventh grade, the school had gone bankrupt. And before that, most of the good teachers had left and the teachers that were still there were cynical and struggling, and it was a mess, the afterschool program when it was just, oh, you know, it was defaulting on the loans for the physical plant. It was just a total mess. So he was right. You know, remember note to self, you know, dad is usually right. Even when he seems wrong, even when you know better. But then what happened was I, I started looking at this in my professional life and I was seeing places where I was either really frustrated and felt like it was not getting anywhere or places wh…

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