Jen Dary, Founder of    Plucky

Jen Dary, Founder of Plucky

“What did you want to be when you were eight years old?” It’s a powerful question that can open up all sorts of conversations and illuminate the way we work together and where we want to go with our career. But who feels comfortable asking this during a 1:1? We're managers, not Oprah—bosses with a big letter B.

Plucky's Jen Dary has the solution. Drawing on four years of leadership coaching, she’s created The Plucky 1:1 Starter Pack to help leaders and teams be more successful together. Listen in on her story, find out what she wanted to be as a kid and discover how she found her North Star.

Do you know a company with a unique story? Tell us about it!


Curious how other shops cultivate teams and leaders? Join us at Owner Camp.

Carl Smith: Hey everybody, and welcome back to The Bureau Briefing. It's Carl and today we have a return guest to The Briefing, it's Jen Dary from Plucky. How's it going, Jen? 

Jen Dary: Hello Carl, hi everybody, I'm great, thanks. 

Carl Smith: It's good to hear your voice. I saw you not too long ago at Owner Summit, you did an amazing workshop that rated out super well on Owner Fatigue.

Jen Dary: I do?

Carl Smith: And everybody seemed full of energy when they left.

Jen Dary: Yes-

Carl Smith: So well done-

Jen Dary: I think they may have needed a nap but fundamental energy, they seemed a little perkier I will say.

Carl Smith: I was going to say a three and a half hour workshop on fatigue, interesting.

Jen Dary: Next time over in yoga maps. 

Carl Smith: [crosstalk 00:00:37]Wait, I wanted to get you on the show mainly to talk about something new that you're doing, which you've taken the concept of your company Plucky where you help people be better humans and work better together. And you've created a product in these cards, which are also marketing but also helping people and also extending what it is you're able to offer. So I was just like, "How did this happen?" I want you on the show and I wanted to explain it so. Can you just give a little bit of the background, the origin on how the card idea came up?

Jen Dary: Yeah, totally so Plucky, you kind of said it really well but I will just give it one extra detail to say. About half my time with Plucky is spent leadership coaching. So that tends to be pretty heavy on managers that I'm interacting with on a regular basis. And then the other half of my time is spent in rooms teaching, right? Sometimes it's an annual retreat or sometimes it's a manager training that I've created myself. And I have noticed through all about four and a half years of this that sometimes you stumble on a big question, and I cannot necessarily take credit for some sort of I don't know mathematical research driven questions that I found but sometimes it covers-

Carl Smith: Oh, just take credit, Jen.

Jen Dary: No, but I was saying I didn't go to the library and looked them up.

Carl Smith: There's seven people listening. Seven people, nobody is going to call you on that.

Jen Dary: Well, they didn't come from some sort of Harvard business book. They came from very genuine conversation where every once in a while a question came up that pushed us into 25 minutes of real growth and I could feel it and I could sense it. And anyway, I just used to scroll those in the margins when that would happen. Okay, so then four years in, I've got a big stack of Moleskines and with a lot of these questions collected. And I was at a manager training last fall in San Francisco, and I think it was the question, "What did you want to be when you were eight years old?” And that is one of the ... Oh, it's a big one Carl. And the reason I won't deep dive too much here, but the reason it's big is that of course at eight, nobody is going to be like, "Oh, I'd really love to be a senior UX researcher." Nobody says that, right? They say they want to be a firefighter or they want to be a marine biologist or they want to be a teacher or a doctor, these things.

And I got really interested in those answers because it seemed like there was a spark of something when you're eight that might be illuminated in some part of your job today. And it's probably your favorite part of your job. So actually let's start there, Carl, what did you want to be when you were eight?

Carl Smith: An actor.

Jen Dary: Do you ever feel like an actor today?

Carl Smith: Every single moment of my life. I don't know who I am.

Jen Dary: But it's interesting you said it because I just saw you at the summit. You're up, you're in front of people, you’re public speaking, right? You have a facilitator role, a host in the room. Your job is probably to keep your ... I don't know, whatever tough stuff you're going through in your personal life a little bit off that stage, right?

Carl Smith: Right.

Jen Dary: Hold that space for people and I wonder if you feel like that's part of, I don't know, is that one of your favorite aspects when you're in the room with people and in the front?

Carl Smith: Without a doubt. I mean, getting up on stage, having people come up to talk to me about stuff afterwards, even if I don't know them, it's all of that kind of aspect that feeling like a valuable human, that's connecting others, that's, that's the joy I get out of The Bureau, without a doubt.

Jen Dary: I mean, and it shows and it shows that you're just having a really good time with it. And that is exactly what I started to notice, that somehow there was, I don't know, a little kernel of truth and whatever your early dream was, what you'd grow up to be that is somehow resonating today, no matter what literal job you have, there's a tiny metaphorical component of it. So anywho, we're in this training, I use that to open and one of the people in the room said, "Oh my gosh, this is like a mind-blowing question, Jen, how exciting." And I said, "Cool, steal it, take it home bring it to a one-on-ones next week." Right? "Use it," and she looked at me and she was like, "Ugh, yeah but I mean, I'm not like Oprah and I don't feel like I could say that question to somebody." And the whole room, there's some nodding happening.

And I thought about this a lot after the training was over, "Why is it that someone can be confronted with a piece of content or a question that clearly moves the needle for them and opened up a whole conversation and some growth in the moment, they've been ... right? It's been proven a little bit but they don't feel they can authentically use it themselves." And I like thinking about those sorts of things and I'm good at this stuff. That's why I do my job, but I also understand that it's not everybody's facility to say these things.

So I started thinking a lot about like, "Well, how could you make a tangible piece of permission or social proof or reidentity." And I always would tell people, "Just blame me," right? Go into your one-on-one, say, “Listen, I was talking to this lady last week, she asked this question." If you say that, it's okay, right? Carl, it's magic you ... If somehow you're not trying to say, "Oh, I am now showing up as your boss with a capital B with a big question." It's more, I don't know, people will respond better to it. 

So I'm like, "Let me flip back through these books." So I find all these questions. I had probably like 60 or so and I whittled it down a little bit and I started ... I taped them to index cards one day. And I was trying to sort them out, "Oh, are there categories these fall in?" and I came up with like eight categories: work-life balance, and leadership, and innovation, productivity, stuff like that. And then I talked to my friend [Greg Story 00:06:41] who you know and maybe first ... Do you think all the listeners know Greg Story? Do you want to riff on him for a second?

Carl Smith: Sure, Greg is one of the original founders of The Bureau, was at Happy Cog for a long time, went to IBM and was responsible for hiring a bajillion designers over there and now he's over at USAA. So he's just kind of the nicest, smartest, most excitable person. Jen, I've described you as well. So the two of you working together, I think would be too much energy for anyone walking into the room.

Jen Dary: It's a lot but I ... but we complement each other pretty well. Greg has done all my website design and he's such a friend and fan of Plucky too. And I look up to him in many ways because he's coming from a very different historical career than I have, right? It's really different but we complement each other in these ways because I'm going to have these weird ideas like more recently I'm like, "I should have a subscription service where I make a box and in the box is everything for a one-hour workshop and you get it once a quarter and it's like somehow able to give you a workshop that you could do on your own." Right? And he's like, "All right, let's do some market research." And I'm like, "Fuck market research, I don't want to do any of those-

Carl Smith: Oh, the shiny things.

Jen Dary: Numbers.

Carl Smith: Oh, the shiny things.

Jen Dary: Right.

Carl Smith: They're so shiny.

Jen Dary: Right. So he, it's really tangible and grounding in those ways. So anyway, I'm like, "All right, Greg, I got all these index cards now, can you ... would you want to design something that's print? I know it's not digital." And he's like, "Yeah, cool." So anyway, he had a good time with it, I think. I think as maybe a lot of the people listening to this will resonate with it's been a long time since Story was billable for being in the weeds, right? 

Carl Smith: Right.

Jen Dary: Designing stuff, so I think that scratches an itch for him to sometimes mentor people like me or be involved on the ground with other brands. And so he designed them. And, of course, I was like, "Let's go, let's go, let's go." And it just takes a long time, right? So we had a sample pack that came and the sample pack was the size of a deck of cards and it seemed good. There are a couple things that I thought we could change but it seemed good. And I was like, "Let's order these." And he's like, "I think it should be a lot bigger. I think they should be the size of flashcards." And he ... you should interview him sometime about that decision because I'm not a designer but he had-

Carl Smith: Yeah.

Jen Dary: Instincts that it would feel more luxurious and also more like a tool if they were bigger. So they're like about the size of my hand, they're pretty big. And he ... Yeah, he just he made these things and then I got the sample pack and I just couldn't believe it. I'm sure you have things like this in your business, Carl, but like-

Carl Smith: Right.

Jen Dary: You're holding this in your hand, you're like, "Holy crap, this was an idea I had based on these old Moleskine notebooks-

Carl Smith: [crosstalk 00:09:42].

Jen Dary: Now, it's a thing." And I think the most exciting part, honestly, was imagining, especially ... I ordered a hundred to start, was looking at this box ... these three boxes of a hundred packs of these cards. And we called them a one-on-one starter pack. And just imagining the fact that one-on-ones are happening all around the planet right now because this card ... this pack of cards exists and people are able to maybe talk to each other differently because they can blame the card. They say, "Pull a card, let's answer a question together." And a manager and a report can build trust in this new way that maybe was really awkward before.

Carl Smith: Well, see, and that's what I love about it is that, and I didn't realize this until you started explaining it but it makes it a game, even if you make you bigger and it's a tool, it's still a game. And it's the kind of thing where I don't know, which card we're going to get next.

Jen Dary: Yeah.

Carl Smith: Even if the manager stacks the deck, right? It's ... And then if you're sitting there and you're both taking a turn answering the question, you are building this baseline of familiarity that then you start to understand each other a little better. And to your point, it's not somebody comes in to lead the one-on-one.

Jen Dary: Right, right.

Carl Smith: Right.

Jen Dary: Well that's-

Carl Smith: That's brilliant.

Jen Dary: This is the thing, right? Is that I cannot ... I have no long-term scalability for Plucky if I have to be necessary all the time, right?

Carl Smith: Exactly, yeah.

Jen Dary: I know I'm a good coach and that's great in as many conversations as I can have but there's a lot of world out there that I will never be able to touch, right? So the cards is this ... Well, it's two things. One, is something I can send literally anywhere that people can embrace and sort of start using but second of all, in terms of cost, it's the ... So the pack is $35 and in comparison to monthly coaching or an annual retreat or things like that-

Carl Smith: Totally.

Jen Dary: I really felt an itch that Plucky needed to respond to verticals that are hungry for some of these human-related tools and resources but perhaps don't have the same profit of budget or just money frankly to throw around that tech does. So for me, it feels very important that Plucky have legs in those other places on earth.

Carl Smith: So do you think this is the kind of thing that could help families not just companies?

Jen Dary: Yeah, I mean, I was just laughing about this yesterday with somebody that they were like, "What must it be like to be at your dinner table, Jen?" Because it's so true we always, as we sit down to have dinner, we say like, "What did you learn today, everybody?" Or like, "What ... who was your favorite conversation with today?" It kind of is having one-on-ones every night at my dinner and breakfast table. I definitely think so and I had a trippy moment probably about two weeks ago now. I have a coach myself. And she was coaching me through some just mess of parenting stuff I was handling and struggling with. And she said, "Well, hang on, didn't you just invent some cards? Why don't you pull a card? Try to answer that [inaudible 00:12:46] of parenting." And the card I pulled was, "What is something that worked really well in a previous job? How could we adopt it here?" And it made me reach for the fact that I have a lot of skills professionally, how could I apply one of those to my family?

And I was like, "Oh my god, coach, you're ... [Kelly 00:13:05], she's blowing my mind right now." I literally read through the card. She's helping me see them in a new way. I think people can use them not just in one-on-ones but to kick off a client meeting or brainstorm. You could have them in your Monday morning things with people. It ... Again, it's all really blending down to the fact that I want to talk to you about a real thing but for whatever reason, I don't feel like I can ask you that. And so the card becomes the proxy through which that human interaction is possible.

Carl Smith: I have not got a deck of cards, Jen, and I'm killing myself right now that I didn't grab one. [crosstalk 00:13:42].

Jen Dary: Let ... oh my gosh.

Carl Smith: Because I want one so bad right now. I was just thinking, so some friends were some of the people over at Cards Against Humanity and their origin story was that the founders were going to a party and they were worried it was going to be boring. And so they created the game on index cards. And they went over there and it was a huge hit. And they ... I think I don't think they've even quit their day jobs today. Most of them are like computer scientists and biologists and stuff. Anyway, but I was just thinking, are you going to do holiday packs? Are you going to do special packs?

Jen Dary: I'm going to do stuff. So I don't know whether the next product will be a pack of cards but I ... What resonates a lot for me about Cards Against Humanity, I don't actually own the game but I of course seen it in the wild. I know that ... I think, aren't they the people that dug the hole? That one year or something?

Carl Smith: Probably. They've done the craziest stuff. They sold ... they literally sold poop one year and so over $50,000 worth of poop.

Jen Dary: Yeah, that's what I'm talking about. So okay, what I love about that branding is that they are not a company. They are kind of like an idea that manifests in lots of different ways. And often, it's a pack of game cards but sometimes it's also these like generous, weird projects, or whatnot. And I feel like Plucky is my art project, that it is a company, but I have always believed that Plucky is more than a company—it is a movement. And I am really compelled by empowering the concept of what I call adult development in workplaces, which is the fact that adults, just like kids, are growing and developing. You can track that growth. You can see how the hard stuff that's going on outside of work impacts work and vice versa. 

And so these cards are really fun, sort of dipping a toe in the water of product, which I definitely think I will keep doing but like Plucky's going to be five in September and I just had a coffee last week with a guy who has a lot of big ideas about the spaces that digital and human interactions kind of overlap or maybe I should say digital and in-person. And I have a big intention to have a big kind of worldwide art project happening for Plucky's fifth birthday. And that won't make me a penny, but it's not about that for me. It's about reach and it's about getting people to talk differently. And I think especially given a lot of what's going on in our current events and everything in the world, like we really need that, not just in offices, everywhere.

Carl Smith: Well, and if you look at it, I mean, you're a business person. You're providing for your family $35 at a time, right? It's going to take a lot of cards to be the equivalent of a workshop or a coaching session or that sort of thing, but at the same time, those cards can sell themselves while you're having dinner with your family, right?

Jen Dary: Mm-hmm (affirmative). Mm-hmm (affirmative). 

Carl Smith: That was the thing that got me about The Bureau when I realized we were a product company. It was when I was at a baseball game and suddenly we had a little run on tickets and I went, "This is the weirdest thing." I'm here having a hot dog and a beer with some friends and yet the revenue was coming in whereas it used to be I had to be in with somebody and convince them of something. And so that's one of those crazy things but also what's ... what I think if it's intentional or if it just happened, those cards are going to land on somebody's desk who's never heard of you.

Jen Dary: Absolutely, oh, they have totally have. I think ... we're almost up to 300 packs sold. There's no doubt. They're ... They've ... I think I had my shop assistant pull numbers the other day that I think we are in 11 countries right now and 32 states.

Carl Smith: Whoa.

Jen Dary: Yeah.

Carl Smith: So you're going to have to transcreate these.

Jen Dary: Yeah, yeah, I'm reminded also that another interesting component to this story ... So I have two little boys and the older one is five and he really loves Legos. And we took him for his birthday to the Lego store in San Francisco. And it happened to be right around Halloween and they were doing this little mini build, I think they called them, which is basically in any Lego store. I guess once a month, you could sign up ahead of time to come in for this free little workshop and you get this little tiny package of Legos. And in October, the one was for a witch, right? For Halloween, you could build a little witch. 

And I'm watching this go down in the Lego store and I'm thinking, "Boy, you know what's an interesting job? The person who decides what the build is going to be and who writes the curriculum. That says, 'Every Lego store, here's what we're doing in October. It's a witch. Here's how you teach the kids. Here's what you need to capture, the email address of the parents, the birthday of the kids so you can send a coupon later,'" whatever it is. And I'm thinking, "Now, that is a way ... There's this tiny little thing. It literally is zero dollars. You just have to get on the list for the kid but it's this tiny thing then they take home. What a positive experience they've had with the Lego brand. And it's this little tiny seed pod that maybe then one day you get them to go to Legoland, right? Or maybe you don't but you get them to keep going to Lego store."

And I feel strongly that these cards could be like that too. They are the seed pod that can go many places and maybe I'll get a little trippy here with you in this conversation, have you and I talked about, have we talked about my very long-term vision? I can't remember, maybe not.

Carl Smith: No, we haven't, go ahead.

Jen Dary: Okay, so maybe some of your listeners know the last time we talked on your podcast, we were talking about the fact that I had brain surgery two years ago. I had a brain tumor and I'm okay. And the night before brain surgery, I was an MRI and I had this vision. I didn't tell you about this?

Carl Smith: No.

Jen Dary: Okay, well here we go. So I had this vision, the night before brain surgery, I'm in the MRI, I had this vision of my future. And the vision was I had this really big feeling I was going to be okay. And I saw myself standing in this framed out building that I was building. And I had bought land. It was really green all around. And I was building Plucky Institute-

Carl Smith: Whoa.

Jen Dary: Which is a center for learning, yeah. And so that is ... I'm almost at my two-year mark post-op. And that has been my North Star.

Carl Smith: Wow.

Jen Dary: So I know that for Plucky Institute, I'm going to need money, I'm going to need land, and I'm also going to need reach. And so, for me, my day-to-day business is of course serving clients but that is only a component of it. All this other work, these mini seed pods, right? These mini builds, these cards, these ability to cross verticals, all of that is going to need to really be a momentum if I'm going to get anybody to come to the center and spend their annual retreats there or bring their teams there for retreats or come and learn. And so it's the long game for me. And the cards are really exciting. And I'm so thrilled to imagine them out there in the world changing relationships today, but they are also building something more foundational for this vision I have.

Carl Smith: So when you think about the Plucky Institute as your North Star, I'm just curious, as somebody who doesn't have a coach, who's had guidance from friends things like that but this idea of a North Star, how often do you ask yourself, "Am I headed in the right direction?"

Jen Dary: Oh.

Carl Smith: Or are the things that trigger it? Is there something that you go, "Okay, I've got to make this key decision, which one gets me closer to the Institute?"

Jen Dary: I will be honest and say that until I had that two years ago, I think I was ... I had the instinct of vague direction. I mean, I knew what I was doing with Plucky was resonating with people, right? I was not having a problem finding people who wanted to work together but I didn't really know what it looked like long term. But since I had that vision two years ago, I think about it pretty much all the time. And it's ... I ... sometimes it's as concrete as which decision would get me closer to that but more often than that, it's just really calming, whatever happens to be on fire today is not a problem. It's like, "Okay, this is stressful today, totally cool but this is not the be-all-end-all. There is a longer term be-all-end-all. And whatever I do today will be in service of that. And so even if I mess something up today or even if I don't ... whatever sell the number of cards I wanted or whatever it is." That is not the metric, the metric is something much bigger. 

And it's really fun too to sit around and think about what I would want in that Institute or I had a friend visit last week she's a Victorian lit professor and to think about, "Oh now, this could be an interesting prophet of stuff happening at Plucky Institute," right? Managers in the Victorian era like, "What?" Who doesn't want to go to that three-day [inaudible 00:23:07].

Carl Smith: What?

Jen Dary: Like these sorts of intersections. And I really feel like part of my long-term professional goal is to get everybody to not only use professional development dollars but also sort of self care dollars to realize that investing in their own growth is what's going to make them explode with possibility and live these really interesting lives. So I don't have the curriculum on any level for Plucky Institute but I sure have met a lot of very smart very interesting people that I would love to invite to come teach something there one day.

Carl Smith: Well, I have no doubt it's going to happen. I have no doubt [crosstalk 00:23:45] Institute.

Jen Dary: Thanks, Carl.

Carl Smith: No, I mean, when you set your mind to something ... And you've got ... The core about following a North Star, as somebody who's never had a coach and never really coached, I think is a successful idea that will keep you afloat because heading toward your North Star in a sinking ship is not going to work, right?

Jen Dary: [crosstalk 00:24:03].

Carl Smith: You're going to be submerged before you get there but you've got Plucky, which has a fan base, right? Much like The Bureau has a fan base and we have a responsibility to those fans at the same time, we have a responsibility to ourselves and our families and everyone else. And so that's when we find that alignment. And this institute makes perfect sense that even if it's a location where people can go for the training and it eventually evolves into something, all of that just makes perfect sense. So we're coming up on time. And I hate that, even saying that but-

Jen Dary: That's fine.

Carl Smith: I have one final question for you.

Jen Dary: Okay, do it.

Carl Smith: Jen Dary, what did you want to be when you were eight years old?

Jen Dary: What a masterful bookend, Carl Smith. I wanted to be a teacher and I-

Carl Smith: That would have been my guess.

Jen Dary: Yeah, I set up my stuffed animals and my siblings in front of a little chalkboard and I used to teach them what I learned in first grade. Nobody really wanted to be there other than me. But they were younger siblings so I could make them stay for a little bit. And I went into education, at college I got all the way through to the last class. And then the professor was kind of teaching us, I was going to be an English teacher, and the professor was teaching us how to write a curriculum or a syllabi. And I kind of raised my hand. I said, "Well, what if there's a New York Times bestseller that comes out mid-year, mid school year like January and you want to get budget from the school district to buy that book for your class? Right? What if you didn't have it ahead of time the summer before but what ... how could you kind of be relevant through the year?"

And he looks at me and he's like, "Oh, Jen, don't rock the boat." And I was like, "I'm out, I'm out." And I literally that day went and I dropped education as my double major and I picked up French and writing and that was going to be a minor anyway. And for a long time, I felt like maybe I had betrayed that about myself, right? That I had wanted to be a teacher and go into education and then I went and got a master's in French it. I lived all over the world and did all these really weird things, ended up in tech, what's happening? 

But this is what kind of prompted my initial attraction to this question is I was talking with husband all night. And he said, "Honey, what are you talking about? Of course, you're a teacher. You're just not in like a high school classroom." And he was right and it is my favorite part of my job whenever I get to teach for sure in person in classes but also coaching. I love that spirit of it and so I totally feel like a teacher and the cards are like this tiny way of sending mini teaching moments everywhere where I can't be.

Carl Smith: Well, and the best teachers learn from their students, which obviously these cards came from that so it embodies both sides, which I think is just beautiful.

Jen Dary: Yeah, absolutely.

Carl Smith: Well, Jen, thank you so much for being on The Briefing today. Again, it's always a pleasure, and I'm just so glad you were able to be here with us.

Jen Dary: Yeah, same here. Thanks, Carl.

Carl Smith: You got it. Everybody listening, we'll be back soon and thanks for tuning in, we'll see you then.