Scaling Tech - The Blueprint for Successful Tech Teams

Latest Episodes:

Making Performance Management a Top Priority with Cat Miller Aug 29, 2023

Show notes

Performance Management! Why is it more important now than ever? And how can you make it a top priority in your organization? In increasingly volatile times, is it worth replacing that person on the team who's giving you 20% less than the next candidate could? And when is a good time to do performance reviews?

Cat Miller is the CTO of Flatiron Health, leading an organization of over 400 technologists who are working together to reimagine the infrastructure of cancer care. Cat is a software and data engineer by training, with over a decade's experience in data-focused startups and nine years growing the team at Flatiron (through acquisition and beyond).

Cat is addressing the issue that most companies either find themselves in a state of hypergrowth or attrition – and in either scenario, there's usually an open headcount.

So, if you're growing fast, there seemingly isn't the time to evaluate performance output. And if there's suddenly a hiring freeze, when someone leaves, you don't receive a backfill for that position. Another challenge is that managers are often not incentivized to performance manage because they don't know what's on the other side of that process.

But as Cat and Debbie concur (and we can attribute the sentiment to Simon Sinek), feedback is a gift. And so thinking about where the person you are evaluating wants to be in five years can help the process.

Good managers care about other people, but it is also about thinking about a person's worth and output from the perspective of the business – and the impact that person's performance has on the rest of their team.

This is a fascinating deep dive into the 'Why, How, What, When, Where, and Who?' challenges that performance management throws up. And if we are looking for steady organizational growth and staff prosperity, these are challenges we need to face. Please join us.

"Product managers really know when their engineering team is delivering – and when it's not." - Cat Miller

In This Episode:

- Why Performance Management isn't a Top Priority (when you have open roles to fill)

- The challenge of performance managing someone out of a role that then needs to be filled

- How can we use business urgency to drive performance?

- What are the risks of de-prioritizing performance management?

- Who's asking: Is this the best you can do?

- When is a good time to do performance reviews?

And more!

Resources:

Connect with Cat Miller:

- Website - https://flatiron.com/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

The Path to Becoming a CTO With JP Grace Aug 15, 2023

Show notes

What is it like to take seven months and interview literally hundreds of founders and co-founders of businesses before taking your next job as a CTO?

This is the fascinating story of JP Grace, a seasoned engineering leader who's paved his way in the tech industry with his ability to drive business growth and positive change.

JP Grace is the current CTO of Endear, where he's assisting omnichannel retail brands in driving sales with an easy-to-implement clienteling platform.

How he got to where he is today is a lesson for aspiring CTOs in being intentional about what they want from their next job – and the lengths they are prepared to go to get it.

For JP, this involved reaching out to his network, chatting with VCs, and taking countless interviews just to see if that next company could be the right fit. Along the way, he learned how to incorporate interview feedback so that he could tell his story in a more impactful manner.

Learn what chopping wood meant to JP as he figured out how to present his best self and prepare for when the stars aligned with the right career opportunity.

Your career trajectory can take off too with the intentionality and directionality that JP and host Debbie Madden are astutely discussing in this entertaining episode of Scaling Tech. Please join us!

"You have to spend a couple of hours a week just researching opportunities and understanding 'Is there a business here? What is this company actually doing?'" - JP Grace

In This Episode:

- How JP first got inspired by technology and making new things out of nothing

- What JP learned from interviewing hundreds of business founders over a period of 7 months

- Paying attention to how your message is resonating with the people you're speaking to

- Learning how to wait for the right opportunity to present itself

- What advice does JP have for aspiring CTOs?

And more!

Connect with JP Grace:

LinkedIn - https://www.linkedin.com/in/josephpgrace/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

Onshore vs Offshore Hiring in a Hybrid World with Joe Burgess Aug 01, 2023

Show notes

Which is better: onshore versus offshore hiring? This is an important consideration in today's hybrid world. To answer this question, Scaling Tech's Debbie Madden has brought in Joe Burgess: someone who's tried both approaches in recent months.

Joe Burgess started his career as a software developer and teacher at Flatiron School, after which he transitioned into leading teams of data scientists, engineers, designers, and education professionals to build the education product at Flatiron – and then deliver it to tens of thousands of students.

Joe then co-founded Ribbon Education where he now focuses on education and sales. Building startup teams is second nature to Joe, but as he found out with some of his offshore hire experimentation, mistakes can be made.

This episode is a lesson in, among many things, defining the requirements of the job. Understand those requirements clearly so that a team can communicate at a certain level so that you can attain a certain work level.

And as simple as it sounds, for Joe hiring early on via Upwork, the ability of his tech hires to understand English proved to be a stumbling block.

Most startups can ill afford the resources to teach someone the job, and walking that fine line between finding someone who is suitably qualified to build you a CRM platform and giving a young coder an opportunity is well-considered and elucidated by Joe and Debbie.

How can you go about hiring junior offshore talent? Is timezone important? How do you create the right work culture with a hybrid team? Answers to these questions and more in this week's educational episode of Scaling Tech.

"When you're a brand new startup (and we're just getting going), it's really hard to allocate the resources to teach someone how to do something." - Joe Burgess

In This Episode:

- Joe's early experiences hiring offshore via Upwork

- What are the requirements of the job? Defining those clearly

- The overlap between teaching and management

- The challenges of hiring junior offshore talent

- How to tackle timezone issues

- Understanding your employment law options when hiring offshore

- How to create the right hybrid work culture

And more!

Resources:

- Horsepaste (codenames online) - https://www.horsepaste.com/

Connect with Joe Burgess:

- LinkedIn - https://www.linkedin.com/in/jmburges

- Ribbon Education - https://www.ribbonedu.com/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

Scaling Innovation at Etsy with Matt Holford Jul 18, 2023

Show notes

How do we think about innovation? And then, how do we scale it? Matt Holford is a Senior Director of Engineering at Etsy and a technology leader who's had quite a storied career working as a musician and in various creative digital service agencies.

As such, he has a unique perspective on how to frame scaling innovation.

How do we give staff the space for idea generation? And then, how do we validate and implement new ideas at a company level? For Matt, opening the door for product innovation means being able to have pockets of creative conversation in high-pressure situations.

It's about having the right expectation of bandwidth to take on new ideas – something that is completely distinct from how good the new idea may be.

Setting goals at the right altitude is also important in today's tough economy. You can set big-level innovation goals that then cascade down to each individual team, but those teams may then feel robbed of the permission to innovate themselves.

Looking at innovation through the prisms of the individual, the team, and the organization is one of the creative ways that Matt is coming up with new idea-generation methods. Please join us in this fascinating conversation about the cadence and scalability of innovation.

"The context matters so much in terms of how willing people are to think about technology and engineering as a creative practice." ~ Matt Holford

In This Episode:

- Appreciating how Matt's career has informed his understanding of product development

- How do you take on board engineer ideas while satisfying stakeholder interest?

- Understanding the practice of generating ideas both inside and outside the business

- How comfortable is Matt with 'throwaway ideas’?

- How do we scale innovation in today's tough economy?

- Seeing the time required for idea generation as a sliding scale

- What is the right cadence for idea generation?

And more!

Resources:

- Ideaflow: The Only Business Metric That Matters - https://www.amazon.com/Ideaflow-Only-Business-Metric-Matters/dp/0593420586

- Creative Strategy Generation - https://www.amazon.com/Creative-Strategy-Generation-Creativity-Strategies/dp/0071850112#customerReviews

- Thinking in Bets - https://www.annieduke.com/books/

- The Voltage Effect - https://www.thevoltageeffect.com/

Connect with Matt Holford:

LinkedIn - https://www.linkedin.com/in/mattholford/?trk=public-profile-join-page

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

Build vs Buy - How to Be a Good Partner to Your Vendor With Ian Lotinsky Jul 04, 2023

Show notes

How can we be a good partner when we buy from a vendor? How do we, as the customer, get good at providing feedback? As we partner with the right SaaS companies, how do we get the most out of those partnerships right out of the gate?

On today's episode of Scaling Tech, I am by Ian Lotinsky, a product and team builder who is the CTO at Great Minds, an online ed-tech business. Ian is answering Debbie's questions with his own, such as 'How do we understand the people on the other end of the Zoom call?' and 'How can we learn as much as possible about the people using our products?'

Creating a partnership mindset requires alignment around the question, 'How do we ask questions?' As we embark on a partnership journey, it pays to ask the right questions upfront – at the risk of getting off on the wrong foot. Debbie and Ian delicately unpack this partnership paradox in this intriguing episode. Please join us.

"One thing I've seen and believe and have read is that you tend to hire culture. And so I've certainly recruited folks and built a team that I could entrust partnerships to." ~ Ian Lotinsky

In This Episode:

- How do you create a partnership mindset?

- How do you get to a positive outcome when you first meet a new vendor?

- Alignment around the question 'How do you ask questions?'

- ‘Forming, Storming, Norming, Performing’

- Understanding the Theory of Constraints

- Building trust relationships through empathy

- Upvoting a problem from within the system

- Building a team based on your values

- What happens when it comes time to exit the partnership?

And more!

Resources:

Lead Without Blame - amzn.to/42bMoVs

Connect with Ian Lotinsky:

- Website - https://greatminds.org/

- LinkedIn - https://www.linkedin.com/in/ianlotinsky

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

Stage Appropriate Processes with Don Neufeld Jun 20, 2023

Show notes

Who do we look to as we try to implement stage-appropriate processes within our tech company? Is it the Googles and LinkedIns for their HR and staff incentive policies, or is there a better way to 'right size' our process challenges?

Don Neufeld is the VPE Coach (Vice President Engineering), who offers leadership and performance coaching for VPEs, CTOs, and other engineering leaders.

What makes Don so effective is that he's been there as a startup engineering leader himself, from founder to IPO stage – including CTO of Medium and VP Eng. at both ClassPass and Chartboost.

Today Don is offering insight into first understanding your WHY as a small company and not just following in the process footsteps of tech giants. It's about the fine line between being proactive as a tech leader and doing something when it's actually needed.

It’s also about asking if your process is better, worse, or the same as before, and making relative judgments instead of comparing yourself with companies that aren't at the same stage as you.

What is your 'risk list,' and how are you, as a tech leader, understanding the financial implications of your business as you burn cash to get to market? Growth at all costs may well be undermining your efficiency process, and the new world doesn't look like the old one, so it's important to have a holistic understanding of your business.

Don's insights may help you solve the right problems for your tech business at the right time – saving you time and money further down the line. Please join us.

"A stage-appropriate process is the right process for you – not some abstract, correct, best process. Especially in engineering. This can be really challenging because engineers want to do things the right way, and so the idea of having an optimal or best process is very attractive." ~ Don Neufeld

In This Episode:

- How do we define the optimal process for our organization?

- Anticipating the pain points in our processes (without solving the wrong problems)

- Looking at similar-sized companies for policy and process comparables

- What access do you have to a community of your technical peers?

- How do we know if we've overshot it with our processes?

- When should you be proactive as a tech leader – and when reactive?

- The value of maintaining a 'risk list'

- When to reevaluate your processes if you're restructuring or downsizing

- What is the most common mistake startups make?

And more!

Connect with Don Neufeld:

- Website - https://vpecoach.com/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

LLM Transformation Is the New Digital Transformation with Dan Mason Jun 13, 2023

Show notes

LLM fluency: what is it, why do tech teams need it, and why should we care about it? LLM transformation is the new digital transformation, and Dan Mason, a principal at Stride Consulting, is today's guest to help us understand all we need to know about Large Language Model transformation.

Dan is a prolific product and engineering team leader who's led teams and products at ESPN, People Magazine, Viacom, and more! Dan has put together a course on LLM fluency and so is uniquely positioned to offer tech leaders out there valuable insight on how they can use deep learning techniques and massively large data sets to understand, summarize, generate, and predict new content.

It's about understanding the outlines in the beginning so that by becoming a prompt engineer, you can potentially solve some of the more common customer problems you may be grappling with.

Engaging LLM so you get to the point of initial utility may be a messy, creative process. Still, the upside of having expertise that builds on itself seems well worthwhile for that initial period of experimentation and understanding.

Because it's all so new and happening so very fast, host Debbie Madden is just about the perfect host when it comes to bringing it back to her audience (tech leaders) and what they can do to increase their LLM fluency for better team productivity.

Learn more about the downstream effects of unlocking creativity with LLM and more in this thought-provoking new episode.

(on LLM transformation) "Really, what's going on here is just a creative explosion." ~ Dan Mason

In This Episode:

- What is LLM fluency, and how can you use it in your team?

- What should we expect as we embrace LLM transformation?

- Why is LLM the new digital transformation?

- What new patterns and roles will emerge with LLM transformation?

- How can tech leaders build LLM fluency and capabilities within their teams?

- How do we engage LLM to get to the point of initial utility?

- What areas of constraint does Dan foresee?

- The downstream effects of unlocking creativity

- Is the Age of Specialists now over?

- Which industries should be the most concerned?

Resources:

- Stride's LLM Crash "Course": https://www.stride.build/services/ai-transformation

Connect with Dan Mason:

- Website - https://www.stride.build/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

Detecting Truth with Adobe's Content Authenticity Initiative with Andy Parsons Jun 06, 2023

Show notes

How do we build systems that improve the way we interact with media and with each other? Truth versus Lies when it comes to content authenticity is today's timely topic and I have brought in Andy Parsons, the Senior Director of the Content Authenticity Initiative at Adobe, to consult!

There is a scientific curiosity for tech leaders around how we discern 'truth' from 'lies' in the media. Especially with the advent of AI, how do we prove what content is false?

As Andy clarifies, it's actually more beneficial for us to focus on learning what content to trust, rather than proving falsehoods. Given Andy's position at Adobe – besides being a SXSW speaker and oft-quoted tech expert – he's ideally suited to provide insight on the content process that is ‘Capture, Edit, Publish,’ as well as the open source future of Content Authenticity.

Following on from this is the idea of 'digital provenance' and using metadata that establishes the chain of custody information needed for users to make trust decisions about digital data.

Everyone should have the right to click on a piece of media and know what it is and where it came from. After that, we can make up our own minds about whether it's trustworthy.

With the good work of the Content Authenticity Initiative, this ideal can become more of a reality as we wade our way through 'fake news' and try to appreciate media content for the honest value it can deliver. Bring on the 2024 US election!

"It's about trust. And trust is not between computers and cameras. Trust is between humans and organizations." ~ Andy Parsons

In This Episode:

- What does the Content Authenticity Initiative do?

- Understanding the process of ‘Capture, Edit, and Publish’

- What does digital provenance entail?

- Discerning between publishers who need to be verified and authors wanting to remain anonymous

- How does the Content Authenticity Initiative actually work?

- How accessible will this technology be?

- How will we know whether something was generated by AI?

- Can we use AI to detect AI?

And more!

Resources:

- Content Authenticity Initiative (CAI) Website - https://contentauthenticity.org/

- CAI Open-Source - https://opensource.contentauthenticity.org/

- CAI Twitter - https://twitter.com/ContentAuth

- CAI LinkedIn - https://www.linkedin.com/showcase/content-authenticity-initiative/

Connect with Andy Parsons:

- Twitter - https://twitter.com/andyparsons

- Andy Parsons LinkedIn - https://www.linkedin.com/in/andyparsons/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

Agile Fluency with Diana Larsen May 23, 2023

Show notes

How do tech leaders learn to lead without blame? Today's guest is Diana Larsen, a truly dynamic and inspirational woman who works with global organizations designing high-performance work systems, and innovating team effectiveness – a theme that is top of mind for most businesses these days.

We are chatting about the Agile Fluency model, how Diana supports business leaders in their transition to Agile methods, and her latest book ‘Lead Without Blame – Building Resilient Learning Teams.’

All of Diana's books are required reading for anyone wanting to up their Agile game. Her insights into how teams work through the prism of the Agile Fluency model are fascinating, as is her view on how leadership is changing as our technological world is changing. I trust you will enjoy this episode.

"It starts with the leaders. Because somebody's gotta at least make that stab in the dark to figure out 'Where are we?... Where do we think we are?... and Where are we really?' ~ Diana Larsen

In This Episode:

- What is the Agile Fluency model?

- Is there a 'target' team for the Agile Fluency model?

- Who decides what level of fluency is for them?

- What does Diana see happening when a team member is added?

- A success story of a business that has employed Diana's model

- How do you avoid complacency once you've implemented Agile Fluency?

- How we cultivate more resilient teams - insights from Diana’s new book

And more!

Resources:

- Agile Fluency - http://www.agilefluency.org/

- Diana’s books - https://www.amazon.com/stores/Diana-Larsen/author/B002BM7U7Q?

Connect with Diana Larsen:

- Website - https://www.futureworksconsulting.com/

Connect with Debbie Madden:

- Website - https://www.stride.build/

- LinkedIn - https://www.linkedin.com/in/debbiemadden1/

- LinkedIn Page - https://www.linkedin.com/company/stride-build/

Value Stream Mapping to Improve Product Development with Rob O’Brien May 16, 2023

Show notes

How do we visualize systems to improve product development? And where are the bounds of that system? Today I'm chatting with Rob O'Brien about process mapping, value stream mapping, and more.

Rob is Principal Product Manager at Stride Consulting and has over ten years of product management experience that he brings to this conversation. Rob frames the debate for us by defining the 'socio-technical system' involving people, technology, and processes that all contribute to the overview of how we should see our product development systems.

How do we include the engineers, the finance department, and other organizational leaders to ensure we are creating a system that can improve our products and services and ask the right questions that will ultimately improve the way we do things?

There's a lot that can go wrong if we make assumptions about which part of our organization needs to be involved in process mapping. Rob shares the value of defining the bounds, asking those 'low-level questions,' and how to structure a two-day conference, say, whereby you are bringing in certain departments at key stages.

Value stream mapping to improve product development is a favorite topic of mine and one that Rob provides much insight on. I trust you'll enjoy this conversation.

"I think the next biggest one (mistake), that actually feeds to that first mistake, is really thinking about and defining the bounds of what the system is in your world. So what do you mean by 'system' - and getting alignment on that?" ~ Rob O'Brien

In This Episode:

- What do we mean by 'systems visualization?'

- Where do we get it wrong when we build our product development systems?

- How do we know if we've involved all the relevant stakeholders 'enough'?

- The value of drilling down into some of the 'low-level questions' to ultimately save time

- The importance of having clear definitions so you can go deeper on your processes

- 'If you see something, say something - why it's important to speak up during the process

- Understanding story mapping and other best practice value stream mapping approaches

- How do we understand the specificity of what to capture?

And more!

Connect with Rob O’Brien:

- Website - https://www.stridenyc.com/blog/author/rob-obrien