Get in touch

Postlight joins Launch by NTT DATA! Learn more.

Launching the employee development movement: this week Paul Ford and Rich Ziade talk to Jennifer Dary, the founder of Plucky, “a consulting firm that helps companies with their people.” They discuss the value of retention over hiring, how to reframe thinking about career paths, Jen’s “employee development” approach to human resources challenges for both people and companies, and a pivotal conversation while stuck in traffic on the Verrazano Bridge.


Paul Ford: Hi, this is Track Changes, the official podcast of Postlight, a digital product studio at 101 Fifth Avenue in New York City. My name is Paul Ford. I am the co-founder of Postlight and the co-host of Track Changes.

Rich Ziade: And I’m Rich Ziade, the other co-founder of Postlight. It’s good to see you, Paul. You’re kind of putting it together right now.

Paul: Just getting my day started.

Rich: I know. I know. I know. What does Postlight do, Paul?

Paul: Postlight is a place that, if you come to us and you say, “Hey, I need to build a web app. I need to build a mobile app.” We go, “OK. Tell us what you need.” And we start talking about your business and we figure things out and we talk about the kind of work you do and the problems and challenges you’re facing, and then we figure out what you really need, which, sometimes you just need a little work, you need like a couple weeks of somebody fixing something up for you. But sometimes you need, like, a big old web platform that can handle transactions and deal with commerce and —

Rich: Yeah.

Paul: And do all the tricky stuff that then gets, when somebody opens up the beautiful app in their hand, they’re accessing that platform, actually. That’s how businesses work today.

Rich: Yeah. That’s the other thing, I wanna say one more thing about Postlight without, like, layering it on too thick with the marketing. Sometimes we do high-scale, really complicated big media platforms, and I’m very proud of that.

Paul: Yeah, no, things that, like, 20 million people can hit a day…

Rich: Yes. People think we’re just making little, sort of, three-of-a-kind games, but that’s not the deal here.

Paul: People aren’t thinking about us, which is why we do this podcast.

Rich: All right, enough about us! OK.

Paul: All right.

Rich: We’ve got a guest today.

Paul: Who is our guest?

Jen Dary: Hi!

Rich: Our guest today is Jen Dary. Welcome, Jen.

Paul: Hey, Jen!

Jen: Hi guys.

Rich: How are you?

Jen: So good.

Paul: Jen. Who are you. What do you do?

Jen: Paul. I’m Jen Dary, and I run Plucky, which is a tiny consulting firm out of Berkeley, California, and I’m a leadership coach and consultant for companies about their people.

Paul: Look, this is one of those kind of spongey jobs, like, life coach? Wink, nod, OK?

Jen: Totally.

Paul: So what do you do all day, actually? Can I ask that first?

Jen: Yeah. Sure. That’s so funny, because in a biz-dev call the other week someone was like, “So I just wanna make sure you’re not full of bullshit before I hire you.” [laughter]

Paul: I think that’s a fair question.

Jen: It’s a fair question!

Paul: I think everyone — I get that question all day, frankly. [laughter] So…

Jen: Half my day is spent coaching, it’s all remote, on Google Hangouts. So I coach members of the leadership team, sometimes I do office hours for employees who are…they just need somebody to work through a thing that’s going on at work.

Paul: So people are like, “I have a problem. Can you help me?’

Jen: Yeah. Mmmm hmmm.

Paul: OK.

Jen: And then the other half of my time, I travel to companies to do employee experience audits or company workshops, I love doing annual retreats, like I’ll lead them and teach workshops about how to have hard conversations, or how to build your own career path, stuff like that.

Paul: All right, so people should stick with us to get a little…

Rich: We’re gonna dive into this, yeah.

Paul: Yeah, we’ll get a little, get everybody a little free management coaching —

Rich: Yup.

Paul: Out of the deal. You’re visiting here from…

Jen: Berkeley, Cali.

Paul: From Berkeley, California.

Rich: It’s a smart town.

Paul: It is. A lot of colleges.

Rich: A lot of —

Jen: It is a smart town, but this feels like home, I gotta say. I get off the plane and I’m, like, “What are we doing?”

Rich: Where are you originally from.

Jen: Westchester, New York.

Rich: Westchester, New York. Before we get into this, we have to lay out a disclaimer, Paul.

Paul: Go ahead and disclaim.

Rich: Jen and I worked together for…five years?

Jen: Six?

Rich: Six years?

Jen: Something like that.

Rich: At my old agency, arc90. That’s how we got to know each other. But Jen has ricocheted through life ever since, and she’s doing some really interesting things now, and that’s why she’s here today.

Paul: So now wait, what did Jen do? Jen, what did you do at arc90.

Jen: So here’s what I did: I went in for an interview for no job. Like, really.

Rich: Yes.

Jen: My friend worked for you guys and said, “You’re smart. You should go work for arc90.” And I was like, “…uh, I can’t even turn on a Dell.” This is a problem. Like, why would I go work for a tech company?

Paul: That alone is a hell of a statement. [laughter]

Jen: Right? I know. So I get there and they’re like, “Hey, what do you, what do you wanna do at our company?” I was like, “I don’t know. What do you do?” And we talked a lot, and I…all I really remember was this one thing I wrote in the cover letter, which was, “I’m not into technology, necessarily, yet, but if you want help making your company a community I can help with that.” And I think that’s what started that convo.

Rich: Yeah, I mean, just, a brief insight into the, the deliberations when you came in: like, the partners in the firm were like, “We’re not sure what to do, but we really like her, and she brings a good attitude to the place.” arc90, for better or worse, was kind of a dark place, a little bit. [laughter]

Paul: It was a little dark when I used to go — I mean, physically dark.

Rich: Physically dark, and these were just some pretty intense people that…they weren’t about, “Oh, I made banana bread.” [laughter]

Paul: This, and a big part of that —

Rich: “It’s in the kitchen.”

Paul: A big part of that, I think what’s interesting, right, like, you start arc90, I got to know you maybe about halfway through the arc90 narrative.

Rich: Yeah.

Paul: And I think you started it in a certain place in your own life, and it grew out of that. [laughter]

Rich: That might be true.

Paul: And then about I think halfway through you were like, “I think there might be more to life than this.” [laughter]

Rich: Yeah.

Paul: Like, you got married, you know…

Rich: That’s right.

Paul: You started to, to sort of look at the sunshine more.

Rich: Yeah. That’s right. That’s right.

Paul: And maybe when Jen showed up, you were like, “Oh, sunshine.” Literally, like, here’s a person who is bright and connected, not sure what she’s gonna do, let’s take a gamble.

Rich: Which is something, right? I mean, you…there’s no job rec, like, come on in and we’ll figure it out is a very strange thing, right? It’s like, there’s no role. Usually there’s a role, a slot, and you go and interview for the slot, and then you find people for the slot. Here it was like, “Come in. We’ll figure it out.”

Jen: But let me talk about what that means very tangibly for somebody who maybe is feeling that right now, right? Like, where should I go? I’m feeling maybe sunny, right? Maybe I can offer a company. What that tangibly meant is that I became a copywriter. Like, that’s what, where that interview went. It was like —

Rich: Sure.

Jen: “OK, sure, why don’t you come and write for our product website.” Which honestly was super convenient, because that’s how I met my husband, so great, good job, guys. Thanks for the matchmaking.

Rich: Yes.

Jen: And I started copywriting for the Kindling product website, which was super helpful, because I was, like, a grandma. I was like —

Rich: Yes.

Jen: “What do you mean, API?” In fact, like, some of our older colleagues remember that I used to have this post-it on my monitor: “What is AIR? What is REST?” Which sounds really philosophical, except they were all in caps.

Paul: Yeah, that’s right.

Jen: Like, AIR.

Paul: AIR was the Adobe technology and REST is…

Jen: Yeah.

Rich: An API.

Jen: RESTful.

Rich: Yeah. Which is, you know, I gotta say, when you pause and think that way, and one of the things we took pride in at arc is we liked the idea of demystifying stuff.

Jen: Yeah.

Rich: And speaking in plain English, and not grabbing all sorts of buzzwords and acronyms and what-not.

Paul: We like that at Postlight too, by the way.

Rich: We do like that at Postlight. We love to cut through the bullshit —

Paul: Well —

Rich: And just go to the thing.

Paul: We like to pull the rug out under from people who…are giving you a lot of nonsense and buzzwords.

Rich: Yeah, yeah.

Paul: It’s fun.

Rich: Yeah. That’s a classic consulting move, right, like, “Let me how expensive I am by how confusing I can be.”

Paul: Right.

Rich: And we actually work the other way. And Jen was a great sort of constant sort of monitor of that. If we drifted too far into fancy stuff, she kind of reset us. So you did that for a bit.

Jen: Yep. And then I accidentally started wireframing. Like I would draw stuff on a board — because I think sometimes late at night we would meet QA people.

Rich: Yes.

Jen: So people were like, “Oh, could you stay and go in as a super user or admin and — ”

Rich: Yes.

Jen: “Try these things.” And at some point I started drawing stuff on a board, like, “Don’t you think it should be first I would press that button and then I would get the drop-down, or these kinds of things?” And that’s when Rich one day backed up and said, “Do you wantBalsamiq? Do you want some software for wireframing?” And I didn’t know what that word “wireframing” meant?

Rich: Yeah.

Jen: So I kind of say that I backed into becoming a UX designer because I was really just a grandma in the room who was, like, [grandma impersonation] “What are you saying with those buttons over there?” You know, that kind of stuff.

Paul: Yeah, but you gravitated towards that company, not towards many — you didn’t go to a law firm.

Rich: Right.

Jen: No it’s super true. It’s super true.

Paul: You wanted, you wanted to figure out what was going on in that world.

Rich: And it was a loose place. That’s…

Paul: But there’s also, there’s an indicator here, too, which is you find the loose place and you say, “I’m available to do whatever and I won’t be too expensive and I will work really hard.” And that’s a very powerful signal.

Rich: I gotta tell you, you don’t see that a lot.

Paul: No.

Rich: You rarely — you get a lot of sometimes, uh, “I’m not doing that. I’m this profession.”

Jen: Mmmm hmmm.

Rich: So, which is…I respect it, but also there’s, you know, to bring humility and learn new things is really something, because stuff that you think is below you is something that you actually don’t know how to do, and if you can add that to your list, that’s a powerful thing. So the attitude and humility, you don’t often see it, I have to say.

Jen: This is where I wanna make a plug for people who are studying languages in liberal arts schools. The only reason I could, like, confidently and, like, I don’t know, exist in a boardroom those first few weeks at arc without having a nervous breakdown was the fact that I had lived abroad and I had studied French, so I majored in French, and you know —

Rich: It’s humbling.

Jen: I’ve been to Italy and ordered a pizza without knowing Italian. You read body language, you learn to look at people. Oh, that person in the room is not so satisfied. This one, I could trust. That kind of stuff. And that’s all I would do in those first conversations: I would sit in the boardroom and look at the diagrams of how insurance software was being built.

Rich: Yeah.

Jen: And I just read the room. I didn’t know what those words were, API, like, any of that kind of stuff.

Rich: Yup.

Jen: But I could tell, OK, that person seems pretty confident, knows what they’re doing, they’re empathetic, let me sort of side with that person, and that’s what I always tell people when they’re new to a job, you should be listening for your first three weeks. You’re gonna go in, there’s gonna be a loudest person, you’re gonna think that that’s who you should attach yourself to — you have no idea whether that’s secretly the person everybody hopes gets fired. [laughter] You should be listening, for like, three, four weeks in the beginning.

Rich: That’s a great piece of advice, actually. Listening…when we meet a prospect, we listen. We want to draw as much information as we possibly can. I’m not interested in pitching you the greatness of Postlight for a bit.

Jen: Yeah.

Rich: I wanna understand what’s up. You had a lot of different jobs just at arc.

Jen: Yeah.

Rich: And it wasn’t even like, career path. You went from copywriting to wireframing to QA to HR…

Jen: Yeah, so that’s what —

Rich: To administrative.

Jen: One day somebody comes to me in the Kindling office and was like, “Hey Jen, so you like to talk to people. Do you wanna run HR?”

Rich: By the way, let’s point out, Kindling was a spun-out startup from arc90. Go ahead.

Jen: So I said, “No. I don’t wanna call it HR, because I don’t have a degree in that. But if we call it something else I would love to do that. Hiring, recruiting, all that stuff.” And so we called it Director of Employee Development.

Rich: Yup.

Jen: Which I super loved, and what I thought was gonna be really fun was the hiring. It turns out hiring is a really boring problem. You have a fantastic person who works at your company. You have a great company, you think a lot about the culture. And then they leave, for like, a weird reason you don’t get. And then —

Rich: You’re saying the reason the slot is open is because someone left.

Jen: The slot becomes open because something happens, question mark, you’re not sure. And then you have to spend a lot of money on job boards to find another great, solid fit culturally, you have knowledge transfer, onboarding, blah blah blah, you lose time. You bring them in, and that’s a boring revolving door. So I got much more interested in the complex problem of retention, not hiring.

Rich: Yeah.

Jen: And that, I think, was a turning point for me, mentally because I started thinking about, well how can I have, like, really helpful conversations and listen to the people who currently work here. That’s why I used to coffee breaks on Fridays with people.

Rich: Yeah.

Jen: To hear what was going underneath, you know, their thoughts. And every once in a while you have somebody who’s like, “I wanna leave because I wanna start a yoga studio.” And at that point you say, “Cheers. Good job.” You know?

Rich: Yeah, yeah, yeah.

Jen: But there’s a lot of stuff that can be fixed, or can be cultivated, especially at small organizations where nobody has such a strict ladder, you know?

Rich: Yeah.

Jen: Where somebody could say, “Hey, you know, my background is development, but I kind of like the idea of managing, or maybe I’m pretty organized, and I could do product stuff.”

Rich: And the truth is many people, if there’s a problem and let’s say it’s a problem because of the, the, a relationship with someone in the office…

Jen: Yeah.

Rich: They don’t talk. They just stew. And that’s a tricky thing. Sometimes you’ve got this sixth sense that you can pick up something’s up, and you say, “Hey, can we go take a walk.” But very often you just get, you just don’t know, and it’s not in their personality or in their, in their sort of experience to go and say, “All right, listen, we need to chat about this.” Many people don’t. Probably most don’t. They just sort of stew with it, and then you kind of get hit with it after the fact. So…

Jen: And I think that’s what really became evident in those coffee breaks.

Rich: Yeah.

Jen: Is that sometimes people just need somebody to talk to.

Rich: Yeah.

Jen: They just need somebody to say their piece to, they vent, and then they just needed me to look and say, “What do you think you should do?” “What does your gut tell you?” is the most powerful question on the planet. Humans know their shit. They know what’s going on.

Rich: Yeah.

Jen: When somebody pointedly looks at you and says, “What does your gut tell you?” they almost certainly know what they need to do. There’s a lot of, like, societal barriers — shame, fear of embarrassment, stuff like that, fear of conflict, that they just don’t say their piece. But sometimes if you just have a, I don’t know, another person next to you who asks you that, like, direct question —

Rich: Right.

Jen: It’s a —

Rich: Leave the office…

Jen: Give me three days —

Rich: Go get coffee…

Jen: You’ll go do it. Once you identify that, you’re gonna go fix it yourself.

Rich: Right.

Paul: So speaking of retention, you quit arc90. [laughter]

Rich: Well she did the yoga studio move. I remember where we were. You said, “Let’s take a walk.” We walked, like, down the street, got coffee, and there’s a little sort of courtyard in one of the apartment buildings. I remember exactly where this was.

Jen: I’m so touched you remember that conversation.

Rich: Yeah, of course. And then you started crying because you thought it was a horrible betrayal. [laughter] And I was like, “What’s wrong, Jen?” And I said, she said, “I think I wanna do my thing!” And I’m like, “You need to go do your thing, and I will help you stand your thing up and whatever you need, let me know. I think it’s great that you’re ready to go do your thing.” You know, I’m an entrepreneur, so when someone says, “I wanna go try the thing,” I’m excited for them. There is someone else who also went and did their thing, Bill Smart, who I actually, I said, I remember having a conversation with him, which was more like, “Every time you come into my office you talk to me about your thing.” Because we were kind of friendish…

Jen: Yeah.

Rich: Even though he worked at my company. And I said, “You need to go do your thing, and please don’t read this as me nudging you out of the company. This is what you love, and I think you should go give it a shot.” And he left, and he did his thing, and he’s doing well. And you went. And did your thing. So describe…

Jen: Yeah…

Rich: Your thing.

Jen: OK. So if I can just take a half-step back…

Rich: Yes.

Jen: I just need to acknowledge that there was a life thing going on for me then, which is that I had postpartum depression with my first kid. And let me just be really honest and say that that brings a lot of questions to your brain. Like, why am I on the planet? [laughter] What am I doing? You know, should I be home all the time with this kid?

Rich: Yeah.

Jen: Do I get to go to work and have an income and have a schedule, like that sort of stuff. And that led me to a little café on Court Street where I made a very long list of every job I’ve ever had, both volunteer and pay. And I wrote next to each job my favorite thing about it, using, like, a little phrase with a verb, so maybe my work on a farm was like teaching kids how to shear a sheep, right? That’s a true story.

Rich: Can I, can we pause for a second?

Jen: Yeah.

Rich: You’re self-awareness is kind of through the roof.

Paul: Well-documented, right? Like, you write it down.

Rich: You write it down, yeah.

Paul: I have some puzzle about myself at this moment, I will go to a coffee shop with a notebook and I will make a list and I will calculate the verbs. Those are, that’s the word you used.

Jen: And you know, the reason that I say that is because there may be people listening to this who have no idea what their next step is, and what they think their next step is is a title, and that is bullshit. I will just tell you that. People say titles and they mean lots of different things by them. So I think what I wanted to do, which is, like, a good echo of what I do with things today —

Rich: So you’re in the coffee shop, you make this list…

Jen: Yeah! Like I wanted to find out what the hell do I want next, right?

Rich: Yeah.

Jen: And so the three most popular verbs on that list were “leading,” “connecting,” and “writing.” So I thought, cool. If I stay at arc, I need to push for a role in which that is my focus. If I go to another company, I need to look for a role in which that is my focus.

Rich: So you broke it down.

Jen: Yeah.

Rich: You’re not looking for “senior vice president — ”

Jen: Exactly.

Rich: Of blah blah blah.

Jen: I’m looking for verbs. What the hell do I wanna spend my billable hours doing?

Rich: Right.

Jen: And the tiny scrap of an idea also existed that I try to do something similar with what I was doing at arc across the market, which was the people stuff. Because you know what? Leadership teams do not go to therapy because the code is too hard. They go to therapy because they don’t know how to say, “I can’t give you a raise this quarter.” Or they don’t know how to say, “I’m sorry you’re not getting along with that person, but you need to figure that out.” Or, you know, those sorts of things. It’s the people stuff that send people over the edge, and I thought, yo, that’s my jam! I’m really good at that stuff. And I saw that there was space in the market to help at more of a level than just internally somewhere. So that’s why I started Plucky.

Rich: OK, so led to our conversation…

Jen: Yup, yup.

Rich: We have coffee. You’re ready to take the leap. You take the leap. It’s a weird leap, right?

Jen: It’s a weird thing.

Rich: Your feet just don’t land somewhere, do they?

Jen: No.

Rich: You’re just sort of floating for a second.

Jen: And you know, I will take this time to tell a teeny story about how I saw Rich at my little boy’s birthday party like, a month in. And so I said to Rich, he said, “Yo, how’s Plucky going?” And I said, “I don’t have any sales yet.” This is, like, maybe four or five weeks in. And he just laughed and he said, “Oh Jen, you’re not at that point yet.” He said, “You’re planting seeds.” And that —

Paul: Yeah, I love, like, four or five weeks, I mean. [laughter]

Jen: I know! But guys, I’m very…you know, I’m ridiculous with sometimes ambition.

Rich: Yeah.

Jen: And so I swear, I think of that probably twice a week. You’re planting seeds. Because even though now I have a healthy business and it’s running really well and I’m doing a lot of stuff that I just can’t even believe is my day job, I still need to be planting seeds, right? Like that’s called biz-dev. And that was such a powerful metaphor for me to think through, and marketing sometimes feels like slimy and weird to me, but planting seeds does not. And I just always think of that.

Rich: Yeah, it sounds beautiful. Like…

Paul: It does.

Rich: Tulips are coming. [laughter]

Jen: Please write a book. Yeah.

Paul: Well sometimes you plant seeds and something slimy and weird…

Rich: Yeah. [laughter]

Paul: That’s happening. That’s how you grow marketing. OK so what is Plucky?

Jen: Yeah. So Plucky is a consulting firm that helps companies with their people. I think that’s maybe the shortest way to say it.

Paul: So I come to you and I say, “Jen. I have a problem with my people.”

Jen: Yeah. So, uh…

Paul: What do you say next?

Jen: I don’t say anything. I say, “Talk.”

Rich: Are you an HR consultant?

Jen: No.

Rich: OK. So…

Jen: This is an SEO problem for me, actually, but that’s a whole other podcast. [laughter] I am not an HR consultant, because I don’t have a background in HR and I cannot tell you how to get, like, employment insurance information for all your 28 states’ employees, right?

Rich: Right, right. Yeah.

Jen: But I wouldn’t say anything. I would say, “Tell me, Paul. Like, tell me about your people. What’s going on?” And then you would describe things. And maybe I would say, “It sounds like your leadership team could use some coaching, because they haven’t had management training.” And so maybe we would rotate through every week for half an hour, I would talk to somebody different on your leadership team, and we’d just keep going like that, and sometimes, like, that fits squarely with what I was saying earlier, where sometimes people need to talk, but also sometimes people need to talk to somebody who’s gonna normalize what they’re going through. Like, I’ll be talking to somebody and say, “Can I just tell you that this whole week has been, for whatever reason, about underperformers? Like, let me reassure you that that’s a problem for other managers, too, and here’s some ideas for how other people are handling that.”

Rich: Let’s dive into this —

Jen: So that’s the coaching stuff.

Rich: By example, right? Let’s say, um, you do a little analysis and you find that the leadership team could use some coaching.

Jen: Yeah.

Rich: Half hour a week, and I’m one of the leaders now. Go.

Jen: Like, coach you?

Rich: Yeah.

Jen: How’s work?

Rich: OK.

Jen: What’s going on?

Rich: Um…it’s going well. The team performs well. I’m having a little bit of trouble, let me pluck a typical kind of situation, uh, gaining, um…the position and respect from the team. I was promoted two months ago. There’s a great one.

Jen: Promoted two months ago and you’re worried about the level of respect.

Rich: We were five widget makers.

Jen: Mmmm hmmm.

Rich: The owners of the firm said, “You’re a very good one. You’re now the leader of the widget makers.”

Jen: Yeah.

Rich: And that’s weird. And I’m struggling with it.

Jen: So do you miss making widgets?

Rich: I still make them, kind of.

Jen: Yeah, you’re still a little billable.

Rich: I’m still, yeah, for sure.

Jen: Mmmm hmmm.

Rich: For sure. But I’m also responsible, quote-unquote, for my team.

Paul: You’re the first among widget makers.

Rich: I’m the first among widget makers, yeah.

Jen: So some of what you’re going through —

Rich: By the way, I don’t love this.

Jen: You don’t love the managing.

Rich: I thought that was the right place for me to go.

Jen: Right.

Rich: But now a third of my time is the managing, and I like making the widgets.

Paul: And I feel kind of bad about it, a lot of the time. Like, I’m not doing a good job as a manager.

Rich: I’m not doing a good job as a manager, and I know what I’m killer at.

Jen: So let me pause and say one thing: you can always choose to go back to widget-making. That is not a demotion. Uh…managing widget makers is a, kind of a new identity for you, right? It’s a new currency. Instead of widgets, it’s humans. And that’s a fundamentally different job, friend-o. That is a different ballpark. So I will tell you that I’m maybe just giving you a giant permission slip, but like, at any point, you could decide this isn’t really my jam. But if itis something you think you wanna stick with, there needs to be a little bit of an identity shift for you. Does that resonate at all? Do you see that?

Rich: Yeah…

Jen: That people need to see you differently?

Rich: Well let’s go back to your first suggestion. You know what the thing about that suggestion is? It can’t come from the company.

Jen: Absolutely.

Rich: Because you can’t say, “Hey, why don’t you go back to where you were. It’s not a demotion.”

Jen: Yup.

Rich: You just can’t do it. So having an outsider have that conversation is, is pretty meaningful. Because the truth is, it’s really not.

Jen: No, it’s not.

Rich: And how do you explain it, because all they do is see the ladder, that’s what they see, and, and see progress, like, professional progress, for them. It was an old engineer who I used to work with who used to say, “If I get too good at what I do, I won’t do it anymore.”

Jen: Mmmmm.

Rich: That’s a weird thing, right? Because if you think about it, the best managers aren’t the best engineers, or the best designers, or the best whatever, right? Because it’s a very different role, in fact.

Jen: No, but they think they should be. And I always, I have a lot of clients who —

Rich: Well, money’s tied to it. Let’s be real, right?

Jen: Oh, yeah.

Rich: Usually it’s more money. Usually it’s more, uh, stature, if you’re into that.

Jen: But I will say, like, people worry that they’re gonna, like, phase out of tech. They’re gonna lose their Python skills. They’re gonna, all that sort of thing, whatever the…the weeds were of what their former job was.

Rich: Yeah.

Jen: They’re, like, “I’m gonna be not as good or not…you know, best on the team of that.” And I say, “That is not what needs to happen.” I could literally manage a team of developers. I’m not the CTO. I’m not gonna make technical choices. But my framing of what a manager is is you’re more of a coach. You’re, like, guiding those people.

Rich: Yeah.

Jen: You’re figuring out, well hang on, what’s your deal at work today?

Rich: And do you love that?

Jen: And do you love that.

Rich: right.

Jen: And sometimes that’s really authentic, and I know, like, one company, when you come in, you self-identify as, “I want to be on a mentorship track or I want to be on an expertise track.” Which means that at some point along the way, if I choose “mentor,” yeah, I’m interested in managing. And maybe those people were, like, RAs in college, or, you know, the oldest of three kids, or like, those sorts of life things. Or maybe they say, “I wanna go the expertise track.” At which point they become somebody who speaks about Python, or you know, goes to conferences, tweets about it, those sorts of things. But point being that at that organization, from moment 1 when you are there, you self-identify, not “I want to be promoted to manager,” but that that’s kind of part of me, you know?

Rich: You’re touching on something really, really meaningful here, which is hierarchy is the only paradigm in companies.

Jen: It’s busted.

Rich: It’s all there is, right? And, and doing good means you go up the hierarchy, and the truth is it’s way more complex than that, and the truth is the role changes, and the responsibility changes as you go up the hierarchy. Nobody bothers to stop and say, “Does this fit in with what makes me feel good, etc etc etc.”

Jen: Let me tell you a quick story. So when I got to Director of Employee Development, I started doing performance reviews at arc, right? And we had a young designer who was right out of college who was killing it, and the first year for performance reviews, I said, “What do you wanna do in the next year?” And he said, “I wanna be creative director.” And that was a super weird thing to say, because we didn’t have titles.

Rich: Right.

Jen: And also he was, like, 23.

Rich: Right.

Jen: And there were a lot more people kind of ahead of him, quote-unquote, in line to do that. So I kind of just gave him the best advice I could, [laughter] I was like, “Keep doing what you’re doing!” Then the second year comes by. Same thing, killing it…

Rich: Says the same thing.

Jen: Says the same thing. [laughter] And I was like, “Ugh. OK…” And we get to the third year and he says, “I want to be creative director.” And the third year I started listening, and I said, “What does creative director mean to you?”

Rich: He truly was killing it, though.

Jen: He was killing it.

Rich: This guy —

Jen: He was a super unicorn.

Rich: Saw where he was…

Jen: Super unicorn.

Rich: Yeah.

Jen: So anyway, when I asked him what that meant to him, he wasn’t able to say these words, but it, he was talking about authority, vision, respect, opportunity to mentor. That shit I can work with. So I got him, like, an intern that summer, to report to him, right? So he could test that, before he decided, “I’m going to go into the management track,” right?

Rich: That’s great.

Jen: And so what I’m saying is sometimes we don’t have language for these things. We say titles —

Rich: Yeah.

Jen: For a shortcut, and then you need somebody who can really parse out what you are saying.

Rich: You know, this is huge, because when someone says this, and sometimes we do get approached and say —

Jen: I’m sure.

Rich: “I should be this.” We view it as a crisis. The management team gets together and, like, “What do we do?” I, we don’t want to upset the person —

Jen: Yeah, because it feels like an ultimatum, right?

Rich: They’re very talented. It’s crisis. And the breaking down of it like that, I think, is something that just doesn’t come to mind in terms of management, you know?

Jen: This is what I’m talking about. Everybody gets very paralyzed by this aspect of conflict, but really what you should do when something really intimidating walks into your room, you should get psyched. You should thank it as an opportunity to listen, and say, “Tell me more things.” Don’t respond at all, just let them talk.

Rich: Yeah.

Jen: They will lead you to where they want to go.

Rich: Yeah.

Jen: You will understand what the value is of that title to them. Sometimes it’s literally that, like, their dad always dreamt of that for them. At which point you can then talk about, you know, “How’s your dad?”

Rich: Yeah.

Jen: “How can we make your dad proud?”

Rich: Right.

Jen: You know, like those sorts of conversations.

Rich: Well let me ask you this, I mean, just to push back a second.

Jen: Sure.

Rich: Sometimes people just are into status, and are into more money.

Jen: Yeah.

Rich: What if they just say that?

Jen: That’s…

Rich: “Look, man, I want to be the shit, and I want more money.”

Jen: That is…

Rich: “I’m smarter than everybody.”

Jen: That is a super helpful data point, as their manager —

Rich: Yeah.

Jen: Because now you know what motivates them.

Rich: Right.

Jen: And there may be a certain point in their work tenure with you where that doesn’t fit anymore.

Rich: Yeah.

Jen: And that might mean a departure.

Rich: Right. If those are sole motivators, you’ve got a bit of a challenge, right, potentially?

Paul: Yes and no.

Jen: Well if you’ve got money coming in, and you’re good —

Rich: Well maybe no! They’re killing it!

Paul: If they’re killing it —

Rich: If they’re killing it —

Paul: And look, that’s the sort of person who very clearly will stand up one day and go, “Not getting it here. Gonna go.”

Rich: Yeah. You’re right, you’re right. Sometimes you’re killing it.

Paul: The key is —

Rich: Sometimes the person is just not where they think they are, right?

Paul: Well that’s everybody. Everybody in the world. [laughter] Everybody in the world…deserves a promotion, right? And that’s just life. But what I think with that is, like, you get in trouble when that person is…

Rich: Killer.

Paul: Well when they’re — no, when they’re killer that’s actually great because you’re like, that’s a transactional relationship, and they’re, they’re —

Rich: They’ll get you there.

Paul: I will say, I think one big difference between arc and Postlight is that Postlight is very discipline-focused, so the fo…people come here, and what we encourage them to do is get really, really good in their discipline, rather than simply be loyal to Postlight, and the Postlight ethos. You should be focused on being the best engineer, the best designer, and the best product manager you can. And our responsibility to you is to deliver challenging work that lets you level up, and then we build the business on top of that.

Rich: And then avenues to level up.

Paul: That’s right. That’s right.

Rich: Like…

Paul: And so you —

Rich: That’s the mission.

Paul: You can measure us, and you can measure them very clearly, you can say, like, is this the best engineering team? Is this the best design team? Is this the best product management team? And are we delivering the right kind of work? And you’re always gonna fall short. Always.

Rich: Yeah. Right.

Paul: But you can look at that gap. And that has been very, very helpful as a framing mechanism, because it’s gotten us out of some of those loyalty-based dynamics.

Rich: Mmmm hmmm.

Paul: And some of the, like, “Do they love Postlight enough?” questions.

Rich: Yeah.

Paul: Which are very dangerous, I think.

Rich: Yeah.

Jen: Yeah, let me tell you my simple paradigm for what I think work is, is like two sides of a circle, or two sides of, I don’t know, I need a better metaphor for this.

Rich: A coin?

Jen: Kind of…not really…well, whatever. Two things that connect, right?

Rich: A hockey puck?

Jen: I used an Easter Egg in a recent blog post and I think I sounded like a lunatic.

Paul: Oh, like a plastic Easter Egg!

Jen: Yeah.

Paul: That’s a very mom or dad thing to say, right? [laughter]

Jen: I know. Well it was right after Easter.

Paul: No, exactly, I put — I had to put so many jelly beans in so many Easter Eggs. Yeah.

Jen: Right? And then that click happens, right? So here’s —

Paul: And you run around the house…

Jen: Oh, it’s weird…

Rich: I don’t know what you’re talking about.

Jen: The bunny.

Paul: You didn’t put any jelly beans in plastic…

Rich: No. We just boil them. And put parsley in them —

Paul: No, I spent, like, an hour and a half, we like to recycle the eggs.

Rich: OK.

Paul: And use them year to year.

Rich: OK.

Paul: And then you hide them around the house.

Jen: Oh yeah.

Rich: OK. All right.

Jen: Anyway. Point is — [laughter]

Paul: Click.

Jen: I think you’ve got one side, which is an employee, who has a skillset and a hunger for something. And on the other side you have a workplace, which has a budget, and also has a need. And if those things line up, click. That’s the right hire, right?

Rich: OK.

Jen: Now the problem with humans and companies is that they keep evolving. Aw, freaking annoying humans, right? So at some point that human is gonna be more interested in a different skill, or want to push deeper into something, right? And that’s, that’s gonna unclick for a second, right? And if the company is fine with that, and can absorb that evolution, then click, you’re back. And that’s called retention, right? To make sure you have channels of communication that make sure things keep clicking. At a certain point, one side or the other may decide that they need something that they’re not getting with the other side, and that’s just a departure. So that might mean the person quits, or the company lets them go. And there’s no poison in that. It’s just a very authentic moment of mismatch where —

Rich: Yeah, I can’t get you what you’re looking for, or —

Jen: Exactly.

Rich: Or you can’t get me what I’m looking for.

Jen: And that’s why I really used to push at arc towards the end for that concept of alumni. arc90 alumni, right? Which is that when you leave here, nobody’s mad at you.

Rich: Yeah.

Jen: It’s that you moved into a different circle where things just weren’t working out anymore.

Rich: Yeah. That’s tough. It’s…

Jen: It is tough.

Rich: You try for it, but it’s tough, right?

Jen: Absolutely, absolutely.

Rich: There’s a lot of…

Paul: It works in big consulting firms…

Rich: Yeah…

Paul: It works a few places. It’s very hard to pull off at a small level.

Rich: Yeah, yeah.

Paul: Where there’s a lot of personal dynamics.

Rich: That’s right.

Jen: It’s true, but honestly, if you have healthy communication all along the way, I could have always predicted the next three people that were gonna quit. I just knew it. Because I watched those humans. You could see: somebody had a breakup and they were no longer tied to New York, so that was an opportunity for life, right?

Rich: That’s a big…

Paul: Mmmm hmmm.

Jen: Like, all that kind of stuff. You just, if you know those humans, I think you can watch for that. I was never surprised by anybody flipping a table and quitting.

Rich: We’re close to running out of time, so I want to talk about a couple of other things.

Jen: Let’s do it.

Rich: So Plucky’s doing well.

Jen: Plucky’s great.

Rich: Effectively, you are a one-person consulting firm?

Jen: I’m a one-person shop.

Rich: Shop…

Jen: You know, the thing is, after you get married, everybody’s like, “When are you gonna have a baby?” After you start a business, everybody says, “When are you gonna hire?”

Rich: Yeah.

Jen: That’s the thing.

Rich: That’s funny.

Jen: And so for the last, almost four years —

Rich: Have you thought about it?

Jen: I had an assistant about a year and a half ago, and then other stuff happened.

Rich: Full time?

Jen: No, she was part time.

Rich: But you don’t see getting more people to actually go and do the consulting.

Jen: No, I don’t see, I don’t think that Plucky’s headed towards a whole team of coaches. I think Plucky is gonna be a movement. That’s what I believe. I believe in, um, something that, well, maybe I’ll lay it out like this: you have accountants and you have sales people. They share a currency, money, right? But you would never confuse those personalities.

Rich: Right.

Jen: You have HR, and you have what I’m about to hopefully release to the world, which is that concept of employee development.

Rich: Yeah.

Jen: And I think those are different personalities, although they’re kind of all shoved into HR right now. And I want a movement of employee development. I want companies who are, um, thinking about the currency of humans in a very fundamentally different way.

Rich: Is it a role? They should…

Jen: Oh yeah, sure.

Rich: If you’re big enough, you should hire for it.

Jen: In fact, that’s sometimes my work, is helping an organization find somebody. It’s usually, like, an office manager. It’s the person that everybody cries to. Like, Paul, when you were talking earlier, I thought, “God, he totally could’ve turned into director of emp-dev.”

Rich: Nobody…yeah.

Paul: Nobody cries to you because you’re just gonna blink and look at them. [laughter]

Rich: I…what can you do? This is me. People cry to you, Paul?

Paul: Not so much anymore.

Rich: Mmmmm.

Jen: Yeah, there’s power dynamic stuff.

Paul: Yeah, it’s not a comfortable thing. But when I was, when I’m at someone’s level, yes. People are pretty transparent with me.

Rich: Yeah.

Jen: You know —

Rich: You have nice, just, just warm eyes.

Paul: Right now the only person who would cry to me at Postlight would be you.

[pregnant pause]

Rich: All right, let’s continue, Jen.

Jen: Well let me just say, actually, Rich, I also think about the fact that, you know, I was a very low person on the totem pole at arc, but I remember the times when I got your attention. It was when we were stuck in traffic on the Verrazano Bridge, going to a client. And we had, like, long conversations about life and stuff. And so I would just like to say for people that career path moments are not always in an office.

Rich: Sure.

Jen: They are, and I also don’t want to say they’re always at happy hours, because that’s very limiting —

Rich: Yeah.

Jen: For people who have kids and don’t drink and all those sorts of things.

Rich: They’re also not the place.

Jen: Not always.

Rich: You end up talking about hockey and movies.

Jen: Yeah. I mean, that can, like, raise a social level to a relationship.

Rich: Yeah. It was a happy hour when I found out that Jen was involved with one of the best engineers arc90 ever hired. Actually one of the most talented engineers I’ve ever worked with. And…you know, arc was this sort of cold, dark place, but love grew…

Paul: Someone found light.

Rich: Someone found light at arc, and I just want to say that, you know, people have this, you know, well, I’m not gonna say it. Whatever.

Jen: Thank you. My love story.

Rich: I’m glad we got stuck in traffic on the VerrazanoBridge.

Jen: Me too! Because —

Rich: And you found out that I’m not a cold-blooded capitalist. [laughter]

Jen: No, that’s what I’m saying! Nobody was weeping in that car, but it sure was a moment where I thought, holy crap —

Rich: It’s out of the setting —

Jen: I was stuck with the CEO. I’m gonna ask him about his life, and I learned so much about you and your family and, and vice versa, and I think that those moments are —

Rich: Which demystifies a lot, right?

Jen: Yes, and I think you trusted me differently after those times, right?

Rich: Yeah, I think that’s true.

Jen: I think you knew where I was coming from, and…and you know, you can’t, like, trap your CEO in a car and hope that helps your career path, but I will say that those strange moments can really be powerful in relationships.

Rich: That’s called kidnapping, just to clarify. [laughter]

Paul: Here’s what I would say on a meta level with that, right? It’s that you went in to arc and you said, “Let me be useful,” Jen.

Jen: Right.

Paul: “Let me find a path here.” And you sat down with Rich eventually in a car, and he knew you were useful, and you guys sort of opened up and talked a little bit, and he then had a better model of you. He was just, like, “Oh I get her a little more now.” And that makes it easier for him to help you. It makes it easier for him to say, “You should talk to Jen about that.”

Jen: Well said.

Paul: Right? And that, that is the dynamic you want. It’s less about, like, getting the attention, and just making sure that they know, like, where you’re trying to go, and it’s, it’s sometimes as a, as a boss, you need to be asking, and sometimes you need to be listening, and sometimes you need to just monitor all the Slack channels.

Rich: Yeah.

Paul: But there’s no, like, outcome to what I’m saying here. I’m just sort of, like, there is a dynamic there, it’s not like, getting in the car with the boss and getting their ear, because that can also be really bad and exhausting, depending on the boss.

Rich: Yeah.

Paul: It’s much more about, like, do they know what I want?

Rich: Yeah.

Jen: Yeah. And wow, way to hit that on the head, because nobody knows what they want.

Paul: Right.

Jen: That is the thing. If you know what you want, you will probably get it, because you are so focused and directed. And I will say that it is OK if you don’t know long-term what you want, if you haven’t calculated your verbs, but you, just know what you want next, right? That’s all you need to know.

Paul: So everyone should go out right now and calculate their verbs.

Jen: Yes! You should! And then you should come to work tomorrow and freaking ask for your three verbs. Like, find a way to make that tangible in the situation you’re in, the environment you’re in. Whenever people say their thing about quitting their job, I say, “Don’t quit. Right now you make a bucket list of everything you could get out of that job before you left. Maybe there’s a colleague you always wanted to work with. Maybe there’s a skillset you wanted to develop. A client’s office you wanted to see…”

Rich: Is this the place for you to pull some —

Jen: I just —

Rich: It may be empty.

Jen: Oh, it is! For sure it is. You can get anything out of anywhere if it’s va — I don’t want to say “vague,” but general enough. If you’re just, like, “I want to practice responsibility a little bit more before I leave, right, because I want one more line on my resume before I leave,” do that. Don’t flip a table and quit, because you are losing an opportunity to leverage a lot of stability, people you know, and all that kind of stuff.

Rich: Right.

Jen: So you make that list. And then you get that stuff and then, often, if you start raising your hand for those things before you leave, that’s actually a retention moment, and you don’t leave, because you realize that you had the power and the control to ask for things, and they came your way.

Paul: And regardless, that’s good for all parties. You’re leaving on a high note.

Jen: Absolutely.

Rich: Yeah.

Jen: Absolutely.

Paul: You’re saying, “I’m gonna give this another try. I, it could be both sides, it could be me, it could be them. I’m gonna do this thing. And if that works out, great. And if not, I’m on my way out, but I’ve done a, I did the best job I could.”

Rich: Exactly. And it’s less contentious and a little smoother.

Jen: Yeah, very graceful.

Rich: Yeah. Um, so what do you got going on?

Jen: Mmmm, OK. So my first Google Doc that I ever started with Plucky’s email was a doc called “So Now You’re A Manager.” Because I used to approve budget for, like, developer conferences and design conferences, but I used to watch these people get promoted out of code and pixels into humans and there was no training for them. And so I made an outline, of a course that I wanted to teach, called “So Now You’re A Manager,” and now, almost four years later, I’m doing it! I’m doing a mini conf in Brooklyn this summer, June 28th, 29th, and…

Rich: Where?

Jen: It’s at 61 Local, which is a great bar.

Rich: OK.

Jen: And they have an event space upstairs.

Rich: That’s awesome, you’re doing it in a bar.

Jen: I know!

Rich: That’s great.

Jen: It’s my old hood.

Paul: Which neighborhood is this in Brooklyn?

Jen: Cobble Hill.

Paul: Cobble Hill, OK.

Jen: Yeah. And so I’m gonna teach managers for two days.

Rich: Very cool.

Jen: And tickets are for sale. And I —

Paul: Wait, where are they for sale?

Jen:They are for sale on my website, actually.

Paul: Which is…?


Paul: So I am a recently-appointed manager and I’m a little perplexed about my life…

Jen: Yeah.

Paul: I should go to —

Rich: Or I’m a company —

Jen: Absolutely.

Rich: And I wanna encourage my managers…

Paul: OK.

Rich: My new manager to go.

Jen: Yeah, in fact, I would say, definitely either direction, but like, if you’re a leadershipteam and you have just promoted a manager,be responsible. Give this person some training. Because ‘see you in T-minus 6 months with a major, weird, I don’t know, social problem on your hands, you know?’ Like, the widget guy, right? If you’re promoted out of widgets, let’s just talk about some of that skillset, because that’s not bullshit. That’s a real thing, and could mean the success or not success of that promotion.

Rich: Very cool.

Paul: And it’s…is it all day, two days/

Jen: All-day two days.

Paul: OK, so two days of your life, and you get a good reset, you understand, you’re able to transition a little bit from widget maker to widget maker manager.

Jen: Totally. Plus it gives you a peer network of other people that are going through that.

Rich: Sure.

Jen: So if you need to have a coffee some day and say, “Oh my God, how did you handle this?” You’re gonna get that.

Paul: And it’s at a bar.

Jen: And it’s at a bar.

Rich: And it’s at a bar.

Paul: So it’s two days at a bar. [laughter]

Rich: Two long days at a bar!

Paul: Talking about management.

Rich: Let’s do this.

Jen: And I’m really friendly.

Paul: All right. Now I wanna go. Partly to be in a bar for two days. [laughter] Partly to, uh, to level up my management skills, because I could always use that tune-up. Thank you for coming on the show.

Jen: Thank you.

Rich: This was really cool. Very cool.

Jen: Thank you so much. I have to say that, um, sometimes you don’t know what you think until someone asks you, and it’s very lonely to run your business by yourself, and I love opportunities to talk about it, because it helps me remember what I’m doing.

Paul: Damn.

Rich: I know.

Paul: All right.

Rich: How do you respond to that? Great seeing you, Jen.

Jen: Thank you.

Rich: You’re in Berkeley, but you hop into New York.

Jen: I’m everywhere.

Rich: So let’s see you whenever you’re in New York.

Jen: Thank you.

Paul: So you’ve been listening to Track Changes, the podcast of Postlight, a digital product studio. I am the co-founder of Postlight, my name is Paul Ford. I’m also the co-host of Track Changes.

Rich: And I’m Rich Ziade, the other co-founder and co-host.

Paul: Let’s get out of here.

Rich: Thank you so much. Rate us five stars on iTunes.

Paul: And if you need anything, send an email to We love your emails.

Rich: Yes we do.

Paul: See you soon.

Rich: Have a great week.