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Chad talks to Leadership Coach and Founder of Plucky, Jen Dary, about working with individuals and companies to create healthy dynamics at work. In fact, Plucky just released a new product that aids in doing just that! Manager Weeklies are notebooks designed to help leaders intentionally set up their weeks and track progress. It includes tips and tricks, including useful 1:1 tools. Each notebook is designed to last one quarter. Follow Jen Dary on Twitter or LinkedIn Plucky Manager Weeklies info & order link Newsletter: beplucky.com/newsletter Become a Sponsor of Giant Robots! Transcript: CHAD: This is the Giant Robots Smashing Into Other Giant Robots Podcast, where we explore the design, development, and business of great products. I'm your host, Chad Pytel. And with me today is Jen Dary, founder of Plucky. Jen, welcome back to the podcast. JEN: Thank you. My third time. Three time's a charm. I feel very lucky. CHAD: There aren't many people who have been on the podcast as guests three or more times. So you're in an ever-increasing select group of returning guests. JEN: Thank you. I feel like it's maybe because the Tokyo Olympics have just started, but I feel competitive and ready to take on this third session. CHAD: [laughs] So the last time you were on was October 28th, 2019 is when the episode came out. JEN: Millennia ago. CHAD: Not quite two years ago, but yeah, also a millennia ago. And that was Episode 342 so if people want to go back and take a listen to that. And then before that, you were on Episode 270, which I actually don't even know the date of. It was even longer. So welcome back. You are celebrating the eighth anniversary of Plucky. JEN: I know. I don't really think of it in these ways because I don't have an MBA, or I didn't come from a business background or anything. But definitely when I hit five years, I feel like my husband said something about that. He was like, "Honey, you should be really proud. Not a lot of businesses make it five years." And that was not really on my mind. But now that Plucky is eight, I feel like oh man, I'm just so happy to talk about how businesses evolve and how what you thought it was going to be in year one was different than year three, was different than year five, and of course, it's different than year eight. So we're eight years in, but nothing's the same, and everything's the same. I'm sure you've experienced that too. CHAD: It was actually the eighth year going into the ninth year mark that we at thoughtbot started to make big changes. And it was that idea of coming up on a decade. It started to feel like, wow, there's real momentum here. And instead of thinking about what the next year looks like, what does the next decade look like? And are we the kind of company that is going to last 20 years? And that put us in a different mindset. And I started to think about the impact we were having and the legacy that we would have. And was it big enough for the size of the company that we had? JEN: How old is thoughtbot right now? CHAD: We just celebrated our 18th anniversary. JEN: Oh my gosh. All right. Well, maybe at the very end, you can give me your best wisdom for the ninth year. [laughter] CHAD: Oh jeez. Okay. [chuckles] JEN: No presh, but tuck that in the back of your brain. CHAD: Yeah, get some sleep. That's my best advice. JEN: [laughs] Great. CHAD: That would be great. We can come back to that. JEN: Cool. CHAD: So obviously, it's been a big two years since we last talked. I'm sure a lot has progressed in Plucky. How have things changed? JEN: Well, what's funny is that the two years spread that we're talking about or 18 months or whatever it is, for the most part, overlaps with COVID so far. So by the end of 2019, things were cooking, and everything is good. And even, personally speaking, my youngest son would be entering kindergarten in the fall of 2020. Again, as a business owner, a mom, all those things I was sort of at the end of 2019 hot, so good. And then I was anticipating 2020 to be continued pretty much the same as is. Like, we would keep training managers. I would keep traveling. All that would get easier because the kids are getting bigger, then my kid would go to kindergarten. And I was also finishing a book about...I can't remember if we talked about this before, but I was really sick in 2016. I had a brain tumor diagnosis, and I'm okay now. It was benign. I had this memoir that was eh, I don't know, maybe two-thirds done. All that was the plan for 2020, Chad. And I'm sure this is shocking news to you, but none of it happened, including freaking kindergarten, obviously in person. So on the business side of things, I kept everything stable as best as I could. So coaching kept going because coaching has always been remote. We have some products, and we kept shipping those out as best we could. At the very beginning of COVID, when everybody thought it was this three, four-week hiatus from real life, I recorded a story every day. Because I was like, what can I do for all the world that's working? So I recorded a storytime for Plucky with my kids. And I put it out on social media so that working parents could have another 15 minutes of distraction for their kids. That's how cute I was back then. [laughter] After one month of that, I was like, I need somebody to read stories to my kids. Yikes. CHAD: Yeah. [laughs] JEN: So the big thing that changed was that our manager trainings in person obviously I had to cancel those. So I transitioned from in-person to virtual events, and that has continued. And as of this recording, end of July, I was thinking that our November event this year…it's the 20th cohort of So Now You're a Manager. I was going to have it in person. And just last week, I pulled the plug on that. And I was like, no, we're going to stay virtual a little bit longer because I don't know how to predict what the hell is coming. So again, that sort of stabilizing, right? Like, okay, well, now I know how to do the virtual. That will be the stable choice this year, which is weird to say, but true. CHAD: Yeah. So you just gave a great organic listing of the things that Plucky does, and a big part of that was that in-person So Now You're a Manager training, which, if people remember from the previous episodes, new managers at thoughtbot have attended over the years. It's a really great training for people who become managers. So what was transitioning that to remote like? Because you'd only ever done it in person before, right? JEN: Yeah, totally. The first 11 cohorts were in person, and then we got to 12, and that was supposed to happen in March in Atlanta. We canceled that, and it wasn't until June that we had the 12th, and that was the first virtual one. And to say that I needed to go through stages of grief is probably pretty accurate. [chuckles] My energy in person is so a thing, like a tool of mine and just pulling people together, and making safe space for conversations and all that jazz. So I was like, what the hell is that going to be like on Zoom? And meanwhile, remember I'm watching my first grader go through the shenanigans of Zoom for the end of that year. And I'm like, oh my God, how am I possibly going to get grown-ups on this and paying attention and not being distracted? So a couple of things, I will say number one is I definitely interviewed four or five people in the industry who are good at virtual events, and I tried to get their deepest wisdom about it. The second thing is that I made the cohorts smaller. So in person, we have around 20 to 22 max, and in virtual, we do 10 to 12 max. And so that got a lot smaller. Also, instead of being two days back to back, I broke it into three half days which is just a different ask. And I wasn't sure if people would bite at that. I tried to mimic it after how some people do an MBA on the side. So then they go to work, and they practice the stuff they're learning at the MBA. And so that has been my thought like, okay, you'll be with me basically for a month. We'll have three half days together, usually on a Friday. And then you're practicing in the meantime. So between the times I see you, you're improving your listening skills. You're coming back with anecdotes about hires or tough conversations or whatever. So I won't say that's like a silver lining, but it's just a different beast. And the first day I did it, I mean, I'm telling you, I was on the bathroom floor on my knees like, don't let the internet go out. CHAD: [laughs] JEN: I was so scared. I don't know why looking back. I'm in tech, but I'm not technical. It's my husband who helps me set up a monitor and whatnot. Oh God, I was so nervous. And I just thought, shit, this is the thing I can't problem-solve. If the internet goes out, I don't know what to do, but if someone's upset, I can help them. So it just brought all of my skills in a different environment. And now I feel pretty good about it. I don't know if you found this with your distributed company overall, but I have worked very hard to make sure that it's a blend, of course, this digital experience, but also I use the mail. I use snail mail a lot. So attendees get a packet before we begin. They get a gift at the end, a graduation gift. And yeah, I feel like I've learned a lot about how to have a hand-in-hand experience of digital as well as a physical object that they can touch to make that experience more than just a screen. CHAD: Yeah, I think that's important. How did changing the format, reducing the class size, what business ramifications were there for that? JEN: Well, it's way less money. [chuckles] CHAD: Right. Okay, sorry. JEN: No. Oh my God. I want to be very real about these things, especially for people starting their businesses. It's way less money. And also if you think about it, everybody had already bought tickets to Atlanta, and then they had already started buying tickets to...I can't remember what the next one was going to be, New York, I think. So for a lot of the year, everything was, I'll say, comped, but that's not really what's going on. All of a sudden, the amount of seats that I thought I was selling for the year got reduced in about half, and much of that were already pre-bought tickets. So, as a line item, that was way lower. I also think I got...man, I haven't really said this transparently to anybody before, but I'll say it here. I got really scared about what to charge. Do you charge the same thing virtually than you do in person? And so I lowered it, I would say for a year. I lowered it by a couple of hundred dollars for each ticket because I didn't know what the market wanted. And also, I didn't know, oh God, were businesses closing? Were people getting prof dev budgets? Everybody was frozen for a good while. So I'm lucky that now today I'm back up to the same price that it had been before, but it's not as much income per event. And the other thing I'll say which affects money…but again, I want to be transparent for other folks who think about or currently run businesses. One great thing to come out of some of the social unrest of last year is that we now have an equity scholarship for So Now You're a Manager. So in every cohort, be that virtually or in person, I always reserve a seat for someone who's coming from an underrepresented group, so people apply. And that is something that I very happily said I will eat the cost of that ticket because it's important to me to have different voices in the room. And that has been a total awesome thing this year. That just started in January of 2021, but that's something really great that came out of last year. CHAD: Yeah. What did you find that customers wanted, and did it change over time? Was there an appetite for it to be remote, or was there resistance to it? JEN: I think at first people were overwhelmed and didn't want it. That's why I held it from March until June until I thought people were ready. I can tell you categorically that I've had the lowest percentage of parents attend of all time because, let's be real, who wants another kind of obligation? Or also, parents during this time, especially with young children, were not in that growth space necessarily for work because there was so much to keep afloat. So other than the three half days, I also have this optional hour that I throw in just if people can come; there’s this extra exercise that didn't fit in from the original curriculum. And I don't think I've had one parent, maybe one, come across all those cohorts that have been virtual to that. So the optional stuff I see parents opting out of. That said, I saw more folks who maybe either live alone or maybe have a roommate but who are pre-family or some people won't have families but someone who was socially like, "It was so hard and tiring last year." And that sort of swung back around towards the summer and end of summer. I saw much more interest there because I think people were really lonely. CHAD: Yeah. And I also think, at least for me personally and for thoughtbot, that was when the thinking definitely shifted that this wasn't going to be going away anytime soon. And so we came to terms with that and started to then make much more long-term plans and permanent changes. JEN: I think it was also in the...I want to say like early fall when Twitter announced they'd be remote. Like, they have an office, but they wouldn't oblige anyone to ever come back again. And whenever that decision was made, there were a couple of other companies...At that point, I was still living in the Bay Area, and there were a couple of other companies that made similar suggestions. And so again, to your point, there was a revisioning of what the next phase was like or at least what to expect. And so, I think people weren't holding out to go back to normal. It was like, what's the new normal? CHAD: Yeah. So when we first shut down offices and went remote, we were giving updates every two weeks, and then it changed to every month. And then it would be like, "There's really no change. We're going to give another update in April." And then April was, "We'll give another update in May." And when it came to June, we just said, "We're planning on being in this mode for at least the end of the year. Let's start all acting and make this sustainable." So that is when our thinking changed too. JEN: Did you feel like with your CEOness and business responsibility over there...what kept you grounded for all that thing? Because obviously every time you make that announcement or regardless of whether that's in person or just...I don't even know– retention or whatever it is. It feels like you're just building strategy on freaking quicksand. CHAD: It wasn't easy. You feel responsible for everybody's well-being, both financially and everything else. And so the lack of stability…you want to provide it in an unstable world. You want to say, "Well, at least you shouldn't have to worry about this. Let’s provide…" but it was impossible to do. And I'm much more comfortable with uncertainty. I think there's a spectrum of comfortableness with uncertainty, and I'm pretty far on one end of it, and even I was struggling. Same thing with like I'm very much on the spectrum of not having to worry about anxiety or anything like that, and even I was feeling it. And so I was just like...at one point I said to I think it was Diana or wha…
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