Giant Robots Smashing Into Other Giant Robots

395: Energy, Perspective, Priorities, and Intention with Jen Dary of Plucky

September 30th, 2021

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.

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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, 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 one point I said to I think it was Diana or whatever "If I'm feeling this, if I'm getting chest palpitations, [laughs] something's really wrong, and we really need to pay attention to how everybody else is feeling."

JEN: Oh, yeah. I even saw that anxiety obviously with coaching clients. There are some clients that when budgets dried up, there was like an initial drop-off, I would say March, April. But then I feel very lucky that the pipeline was still very strong, and I had clients stay with me or join or whatever.

You remember as well as anybody not only did we have this health crisis going on, which again we still do but my last class...So third of three of the cohort in May last year was a couple of days after George Floyd's murder. And the responsibility I felt, when all these things were going on last summer, it was like, who freaking cares about anything? It's like these huge things. And you start to say nothing matters. There are only three things that matter in life. And then you kept sort of recycling the drain on that.

So here I am going into teaching the third of three classes. And during the third class, I always teach concepts on how to hire, concepts on how to lay someone off and fire someone, which everyone's always very barfy and nervous about. And I try to bring us together and graduate us in what feels like a victorious moment. But that's three days after George Floyd's murder, and everyone is reeling and needing to process. And I remember thinking that morning, I don't know how this is going to go because I was fully willing to rip up the plan and do something different. But at the same time, there's also sometimes they want some structure. Folks want to just show up and take this class and be distracted from what's going on in the world.

So we sort of talked about this a few minutes before we started recording but really, what has been fascinating and challenging about continuing to train managers over the last two years is that these very large things are going on in the background: George Floyd's murder, a lot of social unrest in Minneapolis, the election, COVID, all these things. And you can't just put that away and show up to manager training. It is freaking relevant because it is relevant for them. Of course, it's very meta, but all of my students are then going to go back and be responsible for 3, 5, 7 other people in their day-to-day work. So it was really wild, but again, stretching and a challenge that I met with a lot of intention. I don't know if I was always super successful at it, but I thought a lot about it.

CHAD: Yeah, I think that was the shift that we saw on our team. And what I've heard from people is that enough is enough in several different categories of things. And like, we just can't keep on doing what we were doing before. It's not working, and it is unacceptable. People are angry too. So it's not just processing. It's anger and wanting to see action, wanting to take action. And yet, doing it in a world where we can't actually be together, I think, made it particularly challenging for some people and for managers to know how to meet their team members where they were. And people process things in different ways too, and people need different things.

And at that point, we had hired people who had only ever been remote. So I think the connections that you have with people that you might've worked with in person you can lean on a lot in the beginning. But then you're working with someone or managing someone who you've never met in person.

JEN: Yeah. It's a whole new ball game. And I think that the notion of community has gone through the wringer, not only in the worst, it's a rebirth almost. I think the notion of locally what's going on for you and then who can you see? Who can you have a barbecue with? All of those questions of like, who can I be with? Of course, the internet's great, but the internet has some major, major boundaries to it. And people see that at work, and they see that in training.

CHAD: One of the things we're struggling with in that category now is there are people who live next to each other because we were historically in offices. And as it becomes more possible to get together with each other, and this is something that, as managers, we're trying to navigate, it actually has a huge potential for exclusion now that we have hired a bunch of people who are anywhere.

If the teams that were in-person together but are now working remotely start getting in person again, even if it's just an outing at a park, who's not able to attend that, and how will they feel? And what expectations have we set with them? And then you have just sort of equity and inclusion issues around people we've hired in Brazil since we've gone remote. There's no way for them to come.

JEN: Sure.

CHAD: It's not fair. And navigating that as a team, I think we've been able to do that, but it hasn't been easy.

JEN: I think sometimes the only way to see it is none of it will work. So if none of it will work, then cool. The bar's low. [laughter] Yeah, it's not going to be perfect. And all in person had its issues too. So then, if you just sort of bottom it out and say, cool, cool, cool, there's no one silver bullet answer here. So what that means is yes, as human beings, folks who are possibly able to meet up for coffee will resonate and glow and be psyched to be around some other people. So, how do we say "No," less often to that? Because that's great. That's really something to celebrate. And I'm sure if everybody was in that situation, they would try to take advantage of that too. But then to say, if you're not in that situation, here's another option.

And then, every once in a while, we'll mix those options together and have like a rolling menu with it so that nothing gets too static and paralyzed and presumed. And it's in that flow state, which of course, is more fatiguing because you have decision fatigue, and you got to keep making decisions about it. But if you can just say, "Oh, well, we're going to decide that on a week to week basis or on a quarter to quarter." I probably have said this to you before in one of these other podcast conversations, but I just really think that life is a giant science experiment. So if that's true, then you can just say, "Hey, y'all, for Q3, we're going to try this. And at the end of Q3, we'll ask you how that went, and we'll either keep doing it, or we'll totally change it, or we'll increment it."

Software people are really good at this because they know that not everything has to go from 2.0 to 3.0. You could go 2.1, 2.2, 2.3. There are incremental builders. So if you can leverage that metaphor even culturally or socially with the makeup of the team and the way you run things, I don't know; I kind of think that's the best you got.

CHAD: Yeah. And I think we generally have the idea that we trust people and that we can provide the information. And people will generally use that information to make good decisions that are oriented towards fulfillment. So a really good example when it comes to managers is in an environment where if you're meeting in person with someone, one team member and you're their manager, and you're not meeting in person with another, that could influence negatively the other person's path to promotion or the relationship they have with you and just subtly bias you towards the person that you might be able to meet in person with. And so as a manager, making sure people know that, that that is a thing that can happen is a good way to manage that bias because I think generally, people don't want to let that happen, but they might not even realize it, so they can actively manage it.

JEN: Well, it sounds like even in that thought, you are gently nudging people back towards intention and back towards just not sleepwalking through their work, that this is important for us, not only in the distance conversation here but also obviously for race, and for gender and for all kinds of different ways that humans are. We will never get it 100% right and yet intention, and taking a beat, and taking a breath before you move into conversations about promotions or whatever will help remind you hang on a second, remember there's invisible stuff inevitably going on based on who I am and where I came from. How do I make sure things are fair today? Or whatever the reminder needs to be. It sounds like that's...I don't know. It's good that you have that front of mind.

CHAD: So that's one example of remote management. How much of before the pandemic were people who were coming and attending the workshops? Were they managing people remotely? And how much of your curriculum was specific to that, if any?

JEN: My gut says maybe about a third were remote managers. They are definitely with bigger companies that I was seeing that. The small agencies based in Pittsburgh, you know, Austin, those places were pretty localized. But so what you get with a bigger company is also a bit more infrastructure that supports some of these cultural conversations.

And we had it as part of the curriculum, but it wasn't very big, and maybe I would sort of be intentional. There are breakout groups and stuff like that. And I might think I'm going to pair these two together for their practice one-on-one because I know they're both remote managers. I am very intentional about a lot of the pairings and all that stuff, and so I would be thoughtful in that way. But now, on some level, in all these virtual workshops, everybody has an equal footing now. So everybody's kind of screwed, and everybody's also making it work. So that has been a very interesting thing to see.

And I always laugh at this example, a woman who came early on, maybe like the eighth or ninth cohort, and she's a remote manager. And she would say, "Well, I don't have a water cooler. I don't have, like, I'm walking down the hall sensing somebody’s upset or anything." But she would say, "This is going to sound weird, but I keep an eye on how fast they emoji something." So if you have a person who...You know this person in Slack. They're always on Slack, always so supportive, funny, have something to say, a little thumbs-up emoji, or whatever. But if one day they're at work for sure and they haven't said anything about something, she would learn to read the tea leaves like that and check-in. And I just thought that was so clever and very creative.

And what she's alluding to is this level three listening that I teach, which is gut or instinct or intuition. And what she was tracking was basically a change in behavior. And that's pretty much what we're tracking when we're in the office too. There could be many reasons why somebody doesn't emoji something right away. Maybe your daughter just ran into the room. Maybe there's a doorbell. There are a million things. But at the same time, not to be too precious about it but to casually track that at least instinctively. She was doing a good job of meeting the moment as best she could.

CHAD: Are there other ways in which what you've been doing has changed over the last year? What are managers concerned about or challenged by?

JEN: Yeah. First of all, I always had name tags that allowed for pronouns. But this is now certainly part of the curriculum. When we start, I give some social norms and then some tech norms. And so I make the suggestion that in Zoom, after your name, you put your pronouns. And it's not a huge chunk because I really don't feel like I am the best to teach this, but I've added in a DEI component, diversity, equity, inclusion component. And we have some folks in the alumni community who are DEI consultants, so that's great. I always give them shout-outs and refer over if people are looking for that.

I've noticed that people are...I'll say careful, but what I mean by careful is that they are aware of all of the stuff we're talking about, like race and social stuff. Depending on where your office was in the country, the election was sometimes really hard. I think about companies in Ohio or Pennsylvania or swing states where it was not obvious that everybody in the office was on the same page about that. And the way that that stuff comes up and is like this piece of baggage in the room that prevents literally like a website being made. We want to think no, that shouldn't enter. That's not relevant here.

And yet people are careful about both trying to say, "Listen, bring who you are. You're accepted here." And also like, well, sometimes what you're suggesting you believe about the world is harmful. The whole Basecamp thing is a good example of that. And so I found the managers who come to my training to just be open to not only sharing their experiences with that but looking very much for some guidance on that from their peers and then from me.

CHAD: That's sort of what I was saying about people felt like you needed to be changing the way that you were approaching things. It wasn't okay anymore for most people to say, "We shouldn't be having this conversation. It's not a work-related conversation." It affects people's work and their ability to work. It is a work issue. And you can't simply put everything aside. That's one angle of it, but we're not all equipped. We're not all educated. We're not all ready to be able to do that as managers.

JEN: Totally. But with the amount of shit that we have had to handle for the last two years, short of somebody who's a social worker/priest, I don't know who was ready. I feel like a lot of what we're talking about is so resonant for me because all of this is so hard. And if you are alone doing hard things, it's impossible. But the reason that I run the manager trainings the way I do and the reason that I hold onto them after and I put them in a Slack community, they're now alumni of the program. And it's active; it depends on the day. But people have hard questions that they're wrestling with. People have jobs that they're promoting, that they're trying to get people to apply to. It's this active community that goes on afterwards.

Because, honestly, Chad, I feel like a big input into me creating So You're Now a Manager and the community around it was my experience becoming a parent. I was one of the first ones of all my friends. I was the first one of my siblings, and my son was the first grandchild on both sides. And I was like, this is so lonely. All my friends are going out in Brooklyn for dinner. And I was 31. It's not like I was very young or anything, but that's New York. And so I had a moms’ group. And man, that moms’ group got me through those early days because we could all laugh at how hard it was. We could cry together.

And when I looked at the transition that people go through from IC, individual contributor, to manager or some level of leadership, you get responsibility. You have to play the messenger sometimes, something you're not totally down with. You have sometimes competition with peers. You have to manage up sometimes. And then you have these people who come to you with requests: I want a new career path. I want more money. I want a different title. And the slog of that is very reminiscent, on some level, of parenting to me.

So I thought, well, this is not going to be like, here's your book. Good luck being a manager, although books could be helpful. For me, it seemed like there was at least a certain template of a person in the world who could use community too. So I always say you'll be with me for two days or a month if it's virtual. But I can't possibly teach you everything you'll encounter. That said, we can get some critical skills under your belt. And then you can just continue to riff with this peer network. And that has been a very, I would say, unique thing about the manager training I run and something that is so fulfilling to me. I have a very tiny business. Those are, in weird ways, kind of my colleagues, the funny jokes they tell or those personalities. That was another thing that we had to let go of. In 2020, I was going to have the first reunion.

CHAD: Oh yeah. We actually talked about that in the previous episode as an idea.

JEN: Heartbreaking. Yeah, it was called Encore. Basically, it was a follow-up and open to anybody that has already taken SNYAM, So Now You're a Manager. I had people who pitched talks, and we had selected them. And yeah, we had to pull the plug on that. So my hope is that next year we can do that. And now we've got almost...actually; I think we just hit 300 people, so maybe 50 will come, I don't know. We'll see. But I like the idea of providing a space for these folks who were new managers when I knew them and when they came through me but have gained some skills themselves and could become thought leaders in this management space. And whenever the world is ready for it, I'm excited to put that together.

CHAD: Yeah, that's awesome. That sense of community is one thing I've struggled with, to be honest. Because having done this for 18 years, there aren't many people who worked at the company that work there now anymore. [chuckles] We've grown too. So I no longer have the close personal relationship that I had with most people at the company before or close work relationships. And combined with as we've grown, it's have to be more of a leader. You have to put yourself aside. It's harder to always be a servant to others. And then I found that especially difficult last year. And it's part of why I needed to not be CEO anymore and to transition to the COO role. Because I couldn't be in a position where everyone was always looking to me continually to make...and as distributed as we are, one of our values is self-management. But continually always looking to me to be the one who always has an answer, who is the stable one, I needed a break from that. So it's been nice, the transition.

JEN: I was going to say is it better?

CHAD: [chuckles] So it's a little bit different than I expected. So what happened was we made that change. We made other changes, and that was all going well. And then, in February, the largest vaccine scheduling provider in the United States came to us and needed help scaling the infrastructure and all that stuff.

JEN: Oh my God. That's exciting.

CHAD: And so I, along with a crack team of other experienced thoughtboters, went and spent all of our time focused on that. It has pros and cons, which is right as I was transitioning into a new role; I completely got pulled away and started working full-time with that client for a very important cause, which is the reason why we did it and decided it was worth it. The silver lining is it put everyone else in a position where we went very quickly from Chad's no longer the CEO to Chad's not here right now. [chuckles] And that was unexpected. But I think that it had downsides, but it had upsides too in terms of really being in a position where people could come into their own, into their new roles and sort of a forcing function for some of the changes that we needed to make.

JEN: You know, I'll give you major props on that, Chad. Because 18 years and especially, I think this about a lot of things, but especially business here, people get stuck. They really do. They get stuck, especially founders, CEOs. They don't know how to get out of something if they're tired. And there are not a lot of models for what that could look like. The biggest disservice someone could make to leading a company would be to not really be feeling it because that shit trickles down. And if you're tired or if it's not your thing anymore, really, the biggest gift you can give is to go get aligned somewhere else and then hand over the reins to what I keep thinking of as the next generation.

I coach a lot of people, or I work with a lot of people who are in the middle, let's say, so they're not C-suite, and they're not newest managers, but they're sort of senior there. They're totally ready to go. I can't overstate that. [chuckles] Will they mess stuff up? Sure. So did you. Will they have questions? Absolutely. But the next generation of every company it's the most strategic thing that a CEO could do is to think, what happens if I'm not here? That allows you to take a freaking vacation, like take a month off. Or that allows you to meet such a huge civic call, which you're describing here, and step away. Or again, God forbid something happened, and you get very sick; it allows the company to be bigger than yourself.

So I just commend you on even having the courage to step towards COO and then obviously also kind of redirect as needed this year. But I hope that if there are other CEOs listening or folks in the C-suite who are wiped, this is my gentle nudge to them to hand over the reins at some point. Because you'll get a paycheck, I’m sure you can figure that.

CHAD: [chuckles] Being wiped was one small part of it. And I had Diana on who's the new CEO, and we talked about this. We had grown to a certain point. Also, to toot my own horn, I had done a really good job of building a team of managing directors who were really good at what they were doing. And I was no longer the best manager for them. I was no longer what they needed in order to continue to grow. I could do it, but I wasn't the best person for it. So that was the overriding reason to make the change, and being tired and needing to not always be the one that everyone was looking to was certainly a part of it. But yeah, it's been good.

JEN: Yeah. I figured we would get there at some point, but we talked a little bit earlier about how I have this new product coming out in September. So the product is called Manager Weeklies, and it's basically...I got to figure out the exact noun for this. I guess this is the marketing moment. [chuckles] But it's basically a small notebook. The way I think of it is it helps you take a deep breath before your week starts. And so I'm not messing with your to-do lists. Everybody has different versions of that, Trello or wherever the heck you keep it. But before you start the week, it is so important to wonder where's my energy at? What's my perspective? What are the couple of priorities? What am I blocking? Just a couple of invitation questions there.

And then the idea is that you then can do this on whatever, a Sunday night or Monday morning. And then the rest of the week has, I feel like I've said intention 50 times in this conversation but has intention in it. You can decline those three meetings because they're not the highest priority. You can make some space to actually do the work that comes out of the meetings that you're in. And what I have watched over the last maybe three years are my coaching clients who get themselves together at the beginning of the week who have some sort of practice about setting things up in a good way are the most successful. They get the promotions because they look like they know what they're doing because they do.

So anyway, it's called Manager Weeklies. So it's a small notebook. Each notebook is for a quarter. And then, because I'm a coach, I also filled it with other good stuff. Like at the end, there are all kinds of prompts for ways to give praise to people on your team, ways to give feedback, ways to handle conflict, ways to say, "Yes, no, maybe." And then there's a Work Wheel tool at the very end.

And so my hope is that people who just feel like they show up on a Monday already behind that they would find some help with that intention. And I feel like what you're saying is that self-awareness component that came through for you, Chad, to say, I'm not the best at this, and also, I'm a little fatigued and so, therefore, deep breath. Here's the strategy going forward. It wasn't reactive, but there was some thought behind it. And so we'll see this fall people get a chance to try that out.

CHAD: That's awesome. I feel like it's getting back to your roots but also building on it. So for people who don't know, the Plucky Cards were actually the first way that I was introduced to you was someone showing me a pack of those cards. So, where can people find out more about that?

JEN: The best way for people to find any information is just to subscribe to the newsletter. I send it once a month. It's usually a reflection on work, life, something going on there. So if you go to, then you'll be first in the know. What's very funny, Chad, is I have a former coaching client who holds the record now. He was the first one to buy the first pack of cards. He was the first one to buy the second pack of cards. [laughs] And he was also the first one to do this Small Group ticket that I recently did as a little offshoot of Plucky. So anyway, in my mind, I always laugh, and I wonder, I wonder if he's going to grab the first pack of Manager Weeklies this fall.

But you're right. They certainly plug and play with the cards very well where there's even space in the weekly template to say, what's the one-on-one topic for the week? So it could be a card that you pull, and you use, or it could just be something else going on in the world that you want to bring to all the one-on-ones. But I feel like there are a lot of things I'm not great at in the world, but the things I am good at are people. And then I listen to people over and over again through all of these experiences. And I try to hear what else do they need? What weird little thing can I invent that could help them with some of these things that they struggle with?

And I'm also just really mindful of the fact that not everybody has the budget for coaching or for manager training. And I would love for Plucky to be a brand that even if you work for a nonprofit or if you don't have the money to pay for some of those more expensive things that you would have 35 bucks for a pack of cards or 20 bucks or whatever the pricing will be for the notebooks and that you can engage with my brand, even if you're not very wealthy. And I feel like as a person who works and serves an industry like tech, that is always really a priority for me to not only coach or work with the people with the most money.

CHAD: Yeah. If I remember right, you designed the cards, right?

JEN: Oh my God, I wish. No.

CHAD: Oh, okay.

JEN: For the first pack of cards I worked with, I don't know if you know him, Greg Storey.

CHAD: Yeah.

JEN: He's great. Greg Storey did my first deck of cards, and then he moved on, and he's doing other interesting things with his career. So I have a designer who helped me with the second deck of cards called the Manager Pack. So that's questions for managers of managers to bring to one-on-ones, and then the Manager Weeklies are coming out. I've been collaborating with a woman who runs a design little shop called YupGup in Delaware. So her name is Joni. So it is so wild, Chad. I wish that I had any design sense. But it's like, I make these things which look like a terrible PowerPoint. I'm like, here, then there will be a bullet. And then I give it to a designer like Joni at YupGup, and all of a sudden, she has a logo. And then she has some emojis and colors. And I'm like, this is how I felt when I was pregnant, and someone showed me a sonogram, and I was like, (gasps) there's a baby in there.

CHAD: [laughs]

JEN: This is how I felt when she showed me them, and it was so exciting. And I will never be good enough to even be talented at all to make these things myself. But I hold the idea, and then I find someone who wants to help me make that in the world. It's just magical. That is so fun for me. And so I just ordered them. Actually, I ordered 1,000 of them about three hours ago. And so they'll come in August, and I just know it will be very surreal when I open the box and look at them and think about how many people in the world and pens in the world will be used to set intention, to set up people's weeks and hopefully, make a softer and more fair and thoughtful place to work.

CHAD: And one of the things I love about your business and products is that you know you're having an impact beyond that 1,000 notebooks that you put out in the world because each of those people manages 3, 4, 6, 7 people. And if you can make work better for those people, then you have a 7,000-person impact.

JEN: Yeah. And it's funny you say that because I think that recently...I keep saying I'm about to go away for a month or just be out of work for a month as a break after this whole COVID time. Since starting Plucky eight years ago, I didn't really have a model. I am not a traditional business. And even though many people kept saying, "When are you going to hire? When are you going to build the team? When are you going to do all of that?" That is not the shape of Plucky medium-term or long-term. I'm not going to be a coach factory. I certainly could, but then I'd end up super burned out and not liking my job. And then I'd have a sad company, and it would be bad. So I don't want to do that.

CHAD: And that's literally the opposite of Plucky.

JEN: Right. I mean, in the name, right? So, where I have landed as a model is to look at what artists do. And you would never take an artist...I really like Lisa Congdon in Portland. She's a cool, cool artist. And I've heard her speak, and I like her a lot. And what would Lisa Congdon's team look like? She sure isn't hiring other artists to do the work that she's over-signed up for. You get Lisa. And so she has a shop, and then she has partnerships where she teaches at different universities. And as I move into the ninth year here, I'm thinking a lot about what's standing between me and Plucky's shape and what an artist like Lisa Congdon has going on?

And honestly, fully transparently, I think it's that I need to own that Plucky is me. And it's so messy in marketing. Do you use the royal 'we'? We at Plucky? Who is we? And I think that there's some good growth in front of me this fall and next year to say, yeah, I'm Jen, and I run a company called Plucky. And I'm putting this stuff out in the world, and I hope to have ripple effects. And it won't be by hiring 100 people. It'll be just like you described, selling things to X people, and then those people's reports, those ripples will follow down. And I'm really grateful to have found myself in this place because I love coming to work every day.

CHAD: Awesome. Well, even though you love coming to work every day, also enjoy your vacation.

JEN: Oh my God. Thank you.

CHAD: And your time off and your time to reflect.

JEN: Yes, thank you so much.

CHAD: You already mentioned the website, but again, mention that, and then are there other places that people can follow along or get in touch with you?

JEN: Yes, sure. So the newsletter, like I said, is On Twitter, you can look at @BePlucky. I'm on LinkedIn, too, obviously for Plucky. And then I have basically a behind-the-scenes account on Instagram because it was too annoying...Like, what do you take pictures of, Chad, when you're a coach? You can't take pictures of confidential conversations.

CHAD: [laughs]

JEN: So Instagram, I was like, I don't know what to do with this anymore. So anyway, I just have a behind-the-scenes one over there, which is called bepluckster because somebody else had it. So yeah, so all those ways.

And also, I just generally say that if you're a person listening to this podcast and you just wanted to say something to me or ask a question, you should always just email me. It's just I love just hearing from people. And I might not be able to send you a three-page essay back, but I really love just interacting. And if something moved you or made you think about something, whether that was something I said or Chad, you can always just shoot me a note and tell me what you're thinking. I am not precious about that.

CHAD: Awesome. Likewise. So you can subscribe to the show and find notes for this episode at If you have questions or comments, email us at You can find me on Twitter @cpytel. This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thanks for listening. Thanks for joining us, Jen.

JEN: Thank you.

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