[Intro music] Skipper Chong Warson: Hi, I'm Skipper Chong Warson, a coach and design director based in San Francisco, recording in Colorado. Welcome to the second season of How This Works. This is a show where I engage in conversations with experts from a wide variety of fields, diving deep into their specific areas of expertise, plumbing for insights, and learning something along the way myself. In today's episode, Jen Dary joins me to talk about her work as a leadership coach and trainer of managers. Jen, thank you for taking the time to join me. Jen Dary: Thank you, Skipper. I love hanging out with you. And I'm really glad we get to do it in this context for once. Skipper: I know, that's one of the benefits of having a podcast -- you get to invite people that you know and enjoy talking to, so I'm psyched as well. Jen: Awesome. Skipper: Let's start by discussing pronouns. I go by him, how would you like to be addressed? Jen: I am she/her. Skipper: Got it. Thank you. Jen: Thank you for asking. Skipper: Of course. Jen, could you provide a brief introduction about yourself, just a few sentences? Jen: Absolutely. I am from New York originally, and then we lived in the Bay Area for seven years. Now, I live in Arlington, Virginia, which is about 10 minutes from the White House. Basically, we're right next to DC. Skipper: Okay. Jen: And I think I start by location because this can be a longer conversation at some point later, I find my identity is really attached to the place where I am or not. And for me to say I live outside DC, I don't really feel like I'm a DC person, maybe yet, or maybe ever, I don't know. Anyway, that's the first piece of data about me, I have two sons who are eight and 10 years old. I'm married and run a business, which is a big part of why we're talking today. And that business is called Plucky. And with Plucky being almost 10 years old at this point, it is very largely a one-on-one coaching firm where I coach leaders or emerging leaders. But I also teach a class about manager training and, you know, sometimes lunch and learns or speak at conferences about social emotional topics at work. Skipper: Okay. So is there something -- and you're absolutely right, we're gonna dive more into the work matter of it and we might even touch some of the geolocation stuff as well -- is there a surprising aspect of your personality? Or of your background that you'd like to share with the audience? Something that people might not expect? Something that you would feel comfortable sharing? Jen: Oh, yeah, well, I'm a pretty open book. And there's probably 30 things I could say. But one that might be specifically relevant here is I'm the oldest of three kids. And I reach for that not because that's shocking. But there can be some expectations in a family system of an oldest kid. There's also sort of some stuff that comes along with it, like, you're kind of more on the wavelength of the parents a little more often, or you're kind of implicitly in charge of other younger kids more often. And I really can't separate my personality from having grown up in that role, and it leads to so much of what I do on a day-to-day basis, which is, again, aligning, in many ways, with leadership, trying to see their point of view, even though sometimes they come across as super a-holes. Can I say that on this podcast? Skipper: Yes. That's totally fine. Jen: Okay. Like, even though sometimes, sometimes they come across really poorly. And yet the role of founder, owner, CEO, CTO, all these things can also be very complicated. And also, then, you know, I am looking for the folks, it's not that I manage a ton of folks myself, but I'm aware of the dynamic between bringing folks up behind you, and being responsible for other people. And sometimes that's a light touch, like you're responsible for an intern, and sometimes you're responsible for an entire Department of Engineering. But as the oldest of three kids, I think I started feeling that leadership stuff early, maybe earlier than somebody who wasn't in that situation. Skipper: I see. Not to get too far off our topic, but do you find that that question -- that you just brought up where you and your sibling order, were you and your family? Is that something that you often ask either of coaching clients or folks that you're working with? Jen: You know, that's funny, you say that very early in Plucky I remember doing a couple, I won't say trainings, but talks, let's say at a conference, like all agency owners at one point, and I did ask the whole audience, raise your hand if you're an oldest kid, and there was a huge percentage, well over half, I would say, and then of course, you have like, I'm the youngest, but I'm the loudest, you know, they have all kinds of different. I'm an only and so therefore, I got all the attention like, you know, whatever kind of panned out, but I did ask it early on at this point. It only comes out in certain circumstances. Which might be that my client is navigating a combination of where they are and where they came from. Skipper: I see. Jen: So we might explore a little bit about when's the first time you're in charge of something. Or if somebody has a twin -- which is always wild, you know this -- it's all identity, right? That's really what I'm talking about. And so if there's a moment in a conversation where that comes up as something that I think would be relevant to move us forward in the work stuff, I might ask, but I don't ask as often as you think. Now, this is making me want to ask everyone. Skipper: (Laughs) Jen: Takeaway number one. That's right. Skipper: So, thank you for the introductory material. I want to get into the meat of our topic, and the sort of 'this' of How This Works. I gave a little bit of it away in the show's introduction, but I want to hear it from you. What are the subject matters that you're highly knowledgeable in and that we'll be discussing today? Jen: My topics are simply coaching. And that is, in a sense a support system for folks in a workplace. So I am not a soccer coach, not in the athletic sense, right. But I'm a professional coach. And specifically, I am a leadership coach. So that tends to be with people who are either currently in a leadership or manager role or emerging into that, or sometimes eyeballing it from afar, but somebody who's thinking, Oh, leading people, that sounds fun, or that sounds very well paid. I mean, there are a lot of reasons people go in this direction. But if that's sort of on the horizon for someone, they might call me. Skipper: Okay. So Jen, how did you get started in this work? Jen: I said that Plucky is about 10 years old. And right before I started Plucky, I was at a digital agency, and I was the director of employee development. And though I wasn't called a coach, looking back, there were a lot of coachy things going on. And what I kind of mean by that is that I was sort of HR, I was not certified in any of that stuff. But you know, if there was something going on, I was the person that came to me today, we might call ahead of people or people operations, those were not words used a decade ago. And so I definitely had a decent amount of meetings on my calendar where I had to hold confidentiality. And what that meant was that I needed to provide a safe space to hear what was going on and listen well. And for a person to, you know, feel supported in those ways, and hopefully move something forward. So if someone was frustrated with a teammate, and I could hold space for them to process it, dump it all out, we'd look at it together, we decide what's the right way forward? Is it that they should give feedback? Should they go to their manager? Should I be giving feedback, right? When I look back at that algorithm or what was going on, there was coaching. But I didn't call myself a coach until about two years into Plucky I thought it was a consultant. And I was, and also nobody was a coach back then, except for like life coaches. And although Skipper, I would say, weirdly, that sometimes the coaching I do with people does certainly have implications on their lives. It was like I would rather crawl into the sea than be called a life coach in 2012. It was so not serious. It was so undocumented in terms of diplomas, and I had just completed a few years earlier, a Master's of French lit. So, can we get goofier and goofier with my career? You know, I really had to hold some kind of line. And so yeah, someone said, Hey, do you do leadership coaching? And I was like, Yes, I do. And then I put it on the website. And then that's how the whole thing got started. I mean, I already had Plucky, but I never called myself that until someone asked if I provided that service. And that's just how you make a business Skipper, someone asks you, and you put it on the website. Skipper: Yes and... in the scheme of human-centered design, or human-centered business building, like whatever sort of noun and you want to add to the end of human-centered blah, blah, blah, one would argue that you need to be addressing some pain point in the world. And so someone asked you, you looked at it, you made an evaluation, you said, you know, what I'm doing is either super close or not super far. So let's just add it on and see, I mean, the whole idea of hanging a shingle out, is that right? You put your name and your occupation on a sign and you hang it up outside your door, and if people come people come, Jen: It's entirely right. And that is why leadership is an important adjective here. Because if you just say, I am a coach, nobody will come. Skipper: Yeah. Jen: And if you say I am a new mother coach, I am trying to figure out medical documentation because you have a big illness, I am a person who's a leadership coach, or I am a person who helps work life boundaries -- like if you have a specific flavor to the kind of work you do, that is what really people remember. And then they refer. So they're like, Oh, you know, we should talk to Jen Dary. She's a leadership coach, you just got promoted, call her, she's got a manager training program. Whereas if I'm just like, Hello world, I do everything. Nobody remembers you, right? And then the second half of it, of course, is that congratulations, you put it on your website. But if you suck at it, nobody's coming back. So first, you figure out what it's called human-centric, some connection with the fact that there's a gap in the world that needs you. And then, second, you have to be good at it. And then, you know, you persist, right? Skipper: Understanding that there are a lot of different verticals, leadership, coaching, new mother coaching, design coach, like they're all sorts of different versions of it -- can you pull a couple of things out of this work that's interesting for you? Jen: Well, first, I feel like I should say what I think coaching is not. Skipper: Okay, yeah. Jen: So I kind of alluded a second ago to the fact that there's this word consultant. Skipper: Sure. Jen: And what I often say is that consulting means you asked me a question, and I tell you the answer. And that could be, "Well, I have a lot of experience building career ladders, and here's the template and framework you should use." Right? That is consulting. Skipper: Sure. Jen: Coaching is: you asked me a question and I highly suspect that you know the answer already, but for a lot of reasons, you either don't know that about yourself, or you don't know how to word it, or you're nervous to say it, or, you know, a million different versions of what that could be. And so, I am sort of like a backboard, almost neutral, in a way, like on a basketball court, where you're throwing the ball, but I'm sending it back out to you. And one of my frustrations, although I try not to pay much attention to it, but you know, is this feeling that coaches are these almighty wise gurus, that have -- Skipper: -- like sages on the mountain -- Jen: -- millions of followers, please tell us what you think. Skipper: (Laughs) Jen: And, you know, I'm kind of harshing on a number of things there like social media included, but a coach can have opinions, but in the moment, my loyalty is to the person in front of me. I say that all the time, I often coach co-workers, sometimes they don't even know that. And I have to hear sometimes the same story from multiple angles, and I would suck at my job if I'm just telling them, you know, what you need to do right now XYZ and then the conversation is over. It is an insanely complicated way of listening, where I am looking for opportunities to call out something really intuitive or smart someone said, read it back to them, and see what the reverb is there. Skipper: Yeah. Jen: There are moments that I need to -- it's funny to dissect this because I literally never talk about this with people. But I have to track whether what I am saying, is it too harsh, and now they're feeling like they are defending when they didn't really want to be defending. So then I have to walk that back a little bit. Sometimes, a compliment gives them energy, like that was really smart. I'm not faking it. But you know, if I say, Wow, that was really a smart one. And then they kind of have the energy to keep going further. And my whole goal is that by the end of the session, they leave with a different energy, and also, hopefully, self awareness and belief in their own ability to do something. And I'm sure this all sounds very floaty, and life coachy and blah, blah, fluffy. But in reality, it is a really intricate dance. And I think you can't just say, I'm a coach, I'm so cool, I have a billion followers, and I have the wisdom. Like that is not appealing to me in the least to provide any of that service. It is a beautiful interaction that happens between a coach and a coachee. If things are working well, and it just blows me away every time. Skipper: Yeah. So one thing that I was thinking about, as you were giving words to the process of active listening, reflection (here's some of the things that I'm hearing or asking them to reflect on something that they just said something like, how do you feel about this thing that you're describing?), you know, taking those kinds of inventory. Jen: Yeah. Skipper: I think there are some people who might see a framework like this and think, Well, I can do that for myself. I don't need someone to -- and I actually I have a friend of mine, friend and ex co-worker, who said to me offhandedly something about how coaches are not worth the money, not worth the time, not worth the effort -- can you talk a little bit more about the value side of why should I pay someone X number of dollars for some number of sessions to do a thing that I as a human being should be able to do on my own? Jen: Ooh. Skipper: I packed a lot in there. Jen: No, I love everything. The 'should' you just said is doing a lot of heavy lifting, right, which is, I should be able to do this on my own. Skipper: For sure. Jen: So the first thing I would call out is that it's a human adulting moment where sometimes we actually can't do it on our own. And some of us will never agree to that truth. Skipper: Mm. Jen: Some of us will spend the rest of our lives and end our peaceful lives by believing, See, I never needed anyone else. Now, I'm not here to convince people otherwise, right? But I think my honest answer is that if you have someone who is saying, I'm really skeptical of this, and I think it's not worth the money, then almost certainly it would not be worth the money for that person. And they should not call a coach. Because the least successful relationships I have had as a coach are folks who have been referred to me because I will say it like they were they were sent to the principal's office. Oh, you know what you need. Now you need a coach to tell you how to get better, right? Like, Oh, thanks for giving me if designed to fail situation. I mean, I'm good. So I often turn it around, but damn. So if coaching is the reprimand, it's not a great situation. However, if you find yourself in a situation where you're like, I literally don't even know one more idea of how to fix this thing. I have tried so many angles, and I can't even figure this out. And Godspeed, right? Go listen to podcasts, watch webinars, watch Masterclass, talk to all your smart friends, interview CEOs like, bless, go do all those things. And you might end up in a situation where you really still don't know what to do -- in those cases, a coach is really helpful. The last thing I'll say is, as you were talking and kind of laying out that premise, I remember when I had my first son, I was having breastfeeding issues with him. And so we called a lactation consultant, which I never knew was a job. But this is a woman who comes to your house and helps you figure out why your child is not successfully nursing from you. And she blew our minds. And my kid gained like two ounces while she was in our apartment. And it was just so successful. And I will tell you, Skipper, that there are only two times in my life when I needed to call a lactation consultant, if you saw me, Oh, whose I got this lactation consultant Jen, she's amazing. I'd be like Skipper, I'm not nursing anybody over here, I don't need that, right? Skipper: That's right. Jen: So, the validity of it doesn't go away. It's just that I don't need that in this season of my life. And so I would also end on that, that coaching, you probably need a coach for a season. But if you get stuck in a coach, it's the same way. If you got stuck with a therapist, that's not great either. And so I often start my contracts with people by saying, My hope is that you use this as long as you think it's helpful and then you leave. And it's not, you know, there's no shade in that -- we finished the contract. You either renew or you don't. Either way, that's a great victory, you know that you'reasking for what you need. Skipper: Yep. That's a really good analogy. And that notion of things being temporary. Yeah, not necessarily this isn't a, we do this in perpetuity, we do this until it diminishes in usefulness. Jen: And isn't that kind of the whole thing, like all of life, which is that when we get committed or past committed, maybe stuck with a practice or a person or a job or anything that has diminished past the point of being useful or being fulfilling. It's one of the hardest things to do, but to let something go and to say, Well, this is all done now. It's really hard to do. And so that's why I lead with that as a coach, because I don't want people -- I'm sure they'll think I'm nice. I'm sure they won't want to disappoint me at some point or make me feel like I'm sad because they didn't think I was nice, or you know, all the kind of people-pleasing stuff that often coaching clients will have to start with, I don't want to be involved in that matrix for them. I want to be a safe space outside of that. And so I say, You come as long as you need. And then you go, and I'll be really happy for you either way. Skipper: I love this idea of setting a finite amount when you start a relationship. Can you talk a little bit about if there's a typical kind of client that you work with? Jen: Yeah, I'm trying to think of how to paint this with a brush here. Certainly, the largest population would be people in technology. So that could be folks in engineering or design or product or anything in the tech job space, although I also coach professors, academics, and doctors -- I mean, a lot of different stuff at this point, but mostly it's in tech. And then the next cut, I would say, mostly it's in management. And maybe the next next cut, I would say, is probably more than half women. Skipper: Okay. Jen: Yeah. Skipper: I see. So, among these three cross sections of people that you work with as your clients, do you see that there are common challenges that they all face, regardless of either their gender or the field that they're working in? If they're managing or not? Jen: Well, you might be surprised how often I say, Do you want to quit your job? Sometimes, it's a genuine question -- Skipper: Would I be surprised? Because it happens a lot, or would I be -- Jen: All the time. Many, many times a day and week. I say that, because sometimes I'm saying it because -- this just happened this morning, I have a new client and by 10 minutes, and I was like, Are we are we rehabilitating here? Or are we getting out and in some ways, Skipper, I'm asking for myself, because I'm like, All right, what are we doing? And we got a cast of characters emerging in this workplace that is like, woof! And I felt for her very much. Just like, what's our most efficient plan here? Should we just start job hunting? Skipper: That's right. Jen: So sometimes I genuinely want to know, like, do they want to quit their job? Is that part of why we're talking? Skipper: I see. Jen: But sometimes, I use it as a litmus test to get them a little closer to their real feelings about something. So somebody comes in hot like, this happened, and this person said this thing, and then this one said, you know, the thing that always triggers me, etc. So what I might say is, How close to done, are you, huh? And then they might say, Well, I'm not leaving, right. And so even what I just said, There linguistically is, well, there's a boundary. No, I'm not leaving. So I'm testing -- how close are you to the end? And how bad is this? Are you just blowing off steam as you arrive in this conversation? Is it just a lot is on fire and you're tired? Or you're stressed? Or you got a kid or whatever? Or are we actually talking about this here? Because once we've said, Well, we're not leaving. Okay, fine. Now we get to recalculate. Well, what's the work? And if the work is still I'm gonna invest energy, I being a client, and my client wants to invest energy in making that a better situation a better job more fulfilling, blah, blah, then we have really acute things to talk about, like, who should hear this feedback? In what way? When should they hear it? You know, and all that kind of stuff? I can't remember what the question was, I think we're still on track. Skipper: For sure. Jen: Reign me in, Skipper. Skipper: Well, the question was about common challenges that you hear among your various audiences... Jen: Yeah, the other thing I was going to say then, is abysmal lack of support from their manager. And it's not everyone, obviously. Sometimes, I think I might be like an outsourced manager, at least for the career pathing and motivation, and that sort of stuff. I can't obviously give them direction on their tickets and their deadlines and releases. But yeah, either that the manager is checked out, or they're overwhelmed, or they're toxic, or a lot of other things. And what's frustrating is that, as we problem solve their way through it, we have to make space for and account for however this manager is going to digest my client's actions moving forward, right? So if the client is like, I'm going to set this boundary that they can't text me at 9 PM. We also have to spend time in that conversation. Will How will your manager receive that information? And oh, my goodness, it's really, when you look at it, it's like, so inefficient, and so expensive to figure out how to even set a boundary of 9 PM texting, you know, how many hours did someone need to talk to a coach or a therapist or a priest or like, whatever, you know, to get brave enough to say those things? And yeah, it's that feeling of not only not being supported by but often kind of being thrown under the bus by someone that you report to -- it's rough and sometimes that stuff sticks with me, depending on what the content is, and I gotta walk it off or something at the end of the day. Skipper: One thing that you were talking about is asking that question: Do you want to quit your job? Are you done? Like, is this a line in the sand for you? Whoever this person is, whether they've come to you because someone has told them they need to go to coaching or is just signed them up, pick a time on a Calendly, and meet with Jen. However it is that they've come there, there has to be some notion of opting in because -- Jen: Yes. Skipper: You can show up for a coaching session and just sit there for, I mean, I don't know why you would seem, it would seem like an incredible waste of time and energy, but sit there for 50 minutes and not, not talk, I guess or not talk about anything important. So, everyone has different economic needs in terms of what they want. But jobs are things that we sign up for. Jen: Yeah. Skipper: If this isn't a good job, you know, for the return on investment of your time, emotional space, and all of the things that you bring to a job, and that money doesn't pay off for you, it feels like you should be able to opt out. And that's quitting or, you know, putting in your notice, or, you know, whatever it is -- finding something different. Jen: It's real. And often, people don't have someone to say that to you. Skipper: Yeah. Jen: Like it would have a huge amount of stakes to say that to your partner, I might want to quit my job, that's really bigger loaded conversation, because it could have implications on another person's job, or the family's lifestyle or health benefits in this country, a lot of different things, you're probably not saying it to your manager, because of obvious reasons. Skipper: Right. Jen: And your friends are all going to have their own levels of expertise or ability to hear your side of the story without them putting their own stories on it. And so if you do need to unpack, like in a quiet sense, Am I ready to leave this thing, you need someone who really has no involvement in the game. And that can be really useful to parse out. And I'm also not a warm body, I have experience here. And so I will ask you questions, like, the reason we work will change across our lives -- so you might (and listeners, you might ask yourselves this, as you're listening here), What is the purpose of work in my life right now. You may stereotypically start your careers, the purpose of work is, you know, to fund your life, right, like pay rent and food, also to gain experience. And, you know, for some of us, it was like a social life. Skipper: Sure. Jen: I remember I met my husband at work, you know, we played beer pong, back in the days where you were not remote, you know, all these sorts of things were true for the purpose of work, or it was my first job in the industry, there's a lot of stuff there. But then, equally, there will be seasons, where the reason you work is to pay your mortgage or to have health benefits. And there will be other seasons where you make no money, but you're so alive because of the co-workers or the mission or these things. And I say that equally with the fact that there's privilege in us even being able to unpack this a bit. But you are right in that we are saying yes to something every day we show up. And so even if it took three years to quit, if you started that conversation, knowing actually the purpose of work next is not for me to be like ride or die, this product will save humanity, but rather I have a kid and I want to go home at five and I want to spend my weekends with my family. You know, it's valid -- people can work for that reason, it doesn't mean they're mailing it in. But it's really powerful to know that answer, because then you can measure up, Is this job I have, does that fulfill that? Or do I need a new job in which case I should look for a job that allows me to leave at five and go on the weekends? You know, it becomes this really great filter of sorts to figure out which experience you want to say yes to next. Skipper: Yeah. To switch gears to something else that Plucky does. I actually met you several years ago at a manager training -- the So Now You're a Manager product. My manager at the time asked me if I wanted to go to a manager training. And my initial thought was, well, I've already managed people, I'm not a new manager so I'm not sure, but I thought about it more deeply. And I thought, well, I don't have a degree and people management. Right. So I don't know all the ins and outs. So yeah, I'll go to a manager training. It was one of the cohorts that you lead through that training. Can you talk a little bit more about what manager training looks like at Plucky? Jen: Yeah. Well, I think you're right, Skipper, in that we have had experiences of will use of verb managing, but I also mean, leading holding responsibility for maybe even coaching, supporting, we have probably had some experiences before were promoted to manager, because that's probably why you got the job, right? Like you had some kind of intrinsic interest in people and moving them around. Skipper: Whether you were an oldest child or something else. Jen: Exactly, exactly. And so when you come, it's not because you're like, Oh my God, I've never thought about any of this before. Skipper: Right. Jen: Ideally, however, there are some from my perspective, the reason I run this program is number one, because I think you need some real basic skills. And we need to name those things. And we just need to see them in action. So I don't know if you remember, but when we were together, your cohort was in Austin, and I demo-coached someone. So I brought someone up in the front of the room. And I taught you all levels of listening. And then I coached her. And then I would pause her and turn to all of you and say, What are we hearing? What's going on? Not because I wanted you all to say, Oh, she should quit her job. But I wanted you to say she's, she's like kind of bouncing in her chair, I think she's nervous. Or she just said, I'm fine. I'm fine. I'm fine, like three times in two paragraphs. And I'm trying to teach you to listen underneath what her words are saying. Skipper: Yeah. Jen: Because as managers, that is a huge skill, you don't have to have it, but it's a lot easier if you can tell a little bit more about what's going on based on facial expressions. And again, word choice, all that. Skipper: Sure. Jen: So part of my goal with this manager training is for you to either get introduced to or refreshed by some of these skills, listening, how to measure performance, how to fire someone, how to hire someone, retaining people, all that stuff, but almost equally as important, I really think we can do hard things when we're with other people doing hard things. So I wanted community to be a big aspect of this. And so that's why we have cohorts. And that's why every cohort has a mascot. And that's why I bend over backwards to try to make ridiculous metaphors that everyone can remember with fondness, you know, like inside jokes for all 12 to 20 people that were in the room. And that's why we continue in a Slack channel afterwards. And everybody can continue connecting on there. And the reality is, if I could teach you how to be managers in three days, I'd be a billionaire. But that's not how life works. You have to learn stuff, and then go try it, and then learn, and then try it again and reflect on it and laugh about it, and then try it again. Skipper: Right. Jen: Especially some of these social, emotional, and people skills, there's no way you're getting it right the first time; you shouldn't. You will earn your Girl Scout badge along the way, and you need other people to laugh with you alongside. And so that has been really fulfilling for me to see people continue to talk after the class is over. And it might be sort of shocking, but people will sometimes reach out. Hi, Jen, I was in your cohort, I'm sure you don't remember me. And I'm like, Are you out of your mind? I totally remember, you have a kid who's allergic to bananas or you know, whatever it is. Yeah, I know you. I remember you 100%. And, you know, we're at, like, 400 people now. So my brain is very full of personalities involved. Skipper: Sure. Jen: That's a random skill set I have. I'm pretty good at people's names and I'm pretty good at remembering their life stories. Do you remember SNYaM? Do you remember the experience? What do you remember? Skipper: What do I remember? Oh, that's a great reflection question. I -- and you still do this sometimes in the Slack channel, and I think sometimes even post it up on LinkedIn -- but the pizza. Jen: The perspective pizza. Skipper: Yes, the perspective pizza, that's something that I've used off and on, especially -- so this is going to lead into my next question, because doing an in-person training is different than a hybrid or remote or, you know, whatever split it is. And nowadays, some people have had to go back in the office some amount of time. But a lot of companies are doing this, you know, three days on, two days off, lalalala. How either the training, I think it's probably both with the training happening remotely -- actually, you've gone back to in person, right? Jen: No, it's all remote still. Skipper: Still remote? Jen: Yeah. Skipper: Okay, how is the remote piece different than the in-person piece? And how does that parlay into the way that people are working? Jen: Yeah, it's a big old mess, listeners, hang with me here because I'm gonna get very specific, but it'll come together. Skipper: Okay. Jen: So when we were in person, we did two days in a row. Skipper: Yep. Jen: 9:30 AM to 4 something. So, two long days, and it was in a city. So the first 11 cohorts were done that way, then COVID shows up. So then we adapt to a virtual setting. And I should also say that the in-person attendees were probably 20 to 22 people in person. Skipper: Okay. Jen: In the remote Zoom version of this, we are capped at 12 people. And it does not happen over two days. It happens three Fridays in a row for three hours. Skipper: I see. Jen: And there's a bit of science there going on in that. First of all, nobody's nobody's gonna be on Zoom for two days in a row. Like that's not happening. Especially me, can you even imagine? I would peel off the floor by then. And so then the question was, what should we do one day and then one day should we do for half days? And what I came to figure out was that if I made need it more than three classes, I think you'll skip one. Skipper: Mm hmm. Jen: If I make it three, I think I can keep you. But they should be pretty close. So like every week. Skipper: Yep. Jen: If I make it Fridays, it's easier for your boss to say yes. Skipper: Yeah. Jen: And if I make it three hours, I could do 12 to 3 PM Eastern, which means that my Pacific people can join at 9 AM, my Eastern people can maybe like, just check out for the rest of the day. And then there's one optional hour after the second class one, like on Tuesday evening, between classes, not everybody has to come, but I teach like this one specific activity there. So I say all of the detail on that, because it's kind of a fundamentally different class, in a lot of ways. I modeled it off of a part time MBA, where you learn, and then you go practice it. And there's something really great about that, that I think the two days in person didn't allow you to do, it was like, I'm gonna fill you up all the way -- bucket exploding of information. And now, good luck remembering some of that when you go back to the office, right? So I think that was a little overwhelming. But I will also say that the connections between the people are not at all the same as when we were in person. And sometimes that's okay. But that's also a huge reason why I turned that number down from 22 to 12. Skipper: Got it. Jen: So that you had small breakouts, one one-on-one homework with somebody, stuff like that. Lately, I've had alumni assisting the class, so the last couple of years, I've, you know, reached out to somebody who took the class and had them assist, which is a nice dynamic, too. But I haven't gone back to in person. And I think part of it is that this year, we're in a recession. And it's been hard selling tickets anyway. So I don't also want to add the cost of a hotel and a flight and those things. Also, companies are not paying for that as much anymore. So I don't know, it's a little TBD what happens, but those are very fatiguing months for me, when I have the three classes in a row. I'm pretty much working all the time, because I'm monitoring Slack and they have questions around the homework. So it's a really different experience. Still great. Skipper: How is it different helping someone who's either a new manager or wants a refresher course, like you said, how is it different to prepare someone for managing in this mixed mode construct that we have? Hybrid, remote, in person? Jen: (Pause) Skipper: Because the example that you called out of our cohort, this notion of live coaching, you can still do some version of that, I think, where you live coach someone and other people -- Jen: Yeah. Skipper: -- listen in or comment, observe. But I imagine that when you only see people from the top of their head to their shoulders, or whatever their, you know, work camera view -- Jen: Yeah. Skipper: -- there a lot of things that can hide around the edges? Jen: I mean, you are 100% True. And also, it is not unlike their actual job managing people remotely. So even in their actual job, they likely don't have access to more than just the Zoom square anyway. Skipper: Sure. Jen: And yeah, I do demo coach like that. It's still very fun. I will be talking to one person and then time them out and say, Okay, what are we hearing, you know -- it's been adapted, and it is, definitely, it feels different. But like I said, I think we're all swimming in that new language anyway. And so it does kind of port over. But there are things even as a person, So Now You're a Manager or not, I just miss sometimes the energy of teaching live in a room of people. And I miss the little moments and the like body elements and you know, just like walking up to somebody and tapping them on the back and like how are you doing over here? Are we awake yet? As a teacher, there are so many invisible moments that you're consciously and subconsciously pushing out to the room that this is a good time. You're okay here, I got you. Don't worry about work right now that it's hard when we're on Zoom. And then I say, Okay, everybody go pee. I'll be back in 10 minutes, you know, or sometimes you have people who are secretly working on a second screen -- like it both crushes me and I also understand it, but oh, man, it's a different experience to teach like that, as all teachers who taught during COVID know very well. Skipper: Right. We're recording in August of 2023 and just over the past few years, there's been an incredible amount of change in the world, right? Politically, economically, socially, I would say lots of different adjustments. What do you see looking into your crystal ball -- or whatever future sort of pair of glasses you put on? What are the things that you're hearing about from people that you coach or within your business, like, what do you think are the next frontiers in terms of how we're working, how we interact? Etc? Jen: Oh my god, I gotta love this question. Skipper: Thank you. Jen: Well, I'll start with an observation. Skipper: Yep. Jen: More and more and more people are starting to say things like, I'm 48, and I want to retire. I'm 39, and I want to retire. I'm 25, and I want to retire -- more and more people are talking about that earlier. And I see if I unpack that, I think part of it is financial success in tech is so very different that I mean, if you were working in a very different industry, you would, you wouldn't say that until you're like 68, you know. And so the temptation is there, or even the, the chance that something could go public, and that you make some money off of something is obviously greater, although not guaranteed by any stretch of the imagination, but in tech, it's greater. So part of that is the industry and the money that flows through there. But another part of it is that people are waking up in a way to saying, like, I have options. And the great part to me about tech is that, you know, let's say I'm coaching someone, I said, Do you want to leave your job, and they're like, Ah, maybe. One option that they often will say is, I kind of think about doing my own thing. Skipper: Yeah. Jen: "My own thing" is a phrase that I have already pre-selected as a class I will teach one day. Skipper: (Laughs) Jen: And I can't figure out exactly how it manifests; I would love for it to be like a three-day retreat somewhere, where people say I want to step away, I want to do my own thing, I'm going to come and figure out what that needs to look like. Because I don't know whether reality will go in this direction, but Skipper my dream is that like the largest company we have is five people. Skipper: Right. Jen: Obviously, that will never happen like that. But I as many people as possible, I'm always trying to get my girlfriend to start their own businesses. Skipper: Right. Jen: As a woman, I can either work for someone else and wait with cupped hands and hopeful eyes to be promoted into leadership and the C suite. Or I can literally just start at the C suite. Skipper: Sure. Jen: I can start my own thing and be CEO from day one. And I think there's a lot of like fear stuff that came out of COVID, like, oh, women are all quitting their jobs take care of their kids, oh, no, we'll go back in time back in time. And I'm like, right, or they could start their own businesses and have a new bloom of direction. Skipper: Right. Jen: Women have very good intuition about what holes there are in the world and what roles haven't yet emerged. And I'm really very much in support of them taking something and driving with it on their own. And you know, every once in a while, somebody refers somebody for coffee, and I talk with them about their new business. And, you know, I'm always in huge support of that. But if I were going to have a hopeful crystal ball moment, I would hope that more people are able to take agency themselves for their careers. And that might look like a small consulting business that pays all their bills and lights them up in a way and they can live the whole life they want not just their work life, because that's what I feel like Plucky has become, in the beginning, as you probably would guess, I needed like this hustle. You know, everybody was like, when are you gonna hire, that was a pressure. And it turned out that just wasn't the right shape for me in my business. And it was not fulfilling to me to have that. I mean, you're amazing, and you were part of that project. And I just didn't feel like I could manage the staff and continue to give to my practice what I was giving. And now I have Plucky, my kids are growing up a little bit, I wake up at 6:15 in the morning to write a novel I'm working on like, I have all of these other things that are stretching me in very fulfilling ways. So I would like that for anybody else who's interested. And the last thing I'll say on that is, you know, we talked about this a second ago earlier, but I mean, people come out of the woodwork to become coaches now. Right? I should be a coach, I should be a coach, I should be a coach, and people call me obviously after they met me or worked with me. Skipper: Right. Jen: But sometimes Skipper, I think what they are reacting to is a person like me who is very aligned with her work. I am fulfilled by it. It is energizing to me, I love it. And I'm aligned with it. And I think sometimes people see that, and then they think, Oh, I should also be a coach. But maybe they should actually -- Skipper: -- the should, yeah -- Jen: -- just find a job that's aligned with them. And it might not be a coach like you know what I mean. I think they're stealing the wrong takeaway from me, if that makes sense sometimes. Skipper: That absolutely makes sense. It's part of that should that we alluded to earlier. I should be able to manage this myself. But I need -- I don't believe that any one person should be doing it by themselves, I think you need a team. And whether that's a social support team or you have that structure within your relationship at home, you need to have that support to -- even if it's something as simple as like, you walk in the door, and you say, I need to, I need to talk about something that happened today. Or maybe these days, you're walking downstairs, you know, and you say, I need to talk about something that happened today. And I just need a couple of minutes to blow off some steam. Jen: Yeah. Skipper: That's valuable as well. But I, anyway, yeah. So it's about that should -- Jen: Absolutely. You're also kind of connecting another thought for me, which is, when I say that companies would have maximum of five people. I think this is also something brewing in me about what do we lose when we make things bigger? And that is both in our companies, or -- trust me, I go to giant, I buy Ritz Bits, my house has processed foods, I'm not that person. But what we lose when nothing is handmade, nothing is made from scratch, nothing is that -- what do we lose, when we have, here we go, I'm getting a little much here. But like mega churches with 45,000 people in them, what is happening, you know, like, none of that is intimate to me, and interesting to me. And so the older I get, even though I'm a massive extrovert, and I get very energized by people, I really have very few people that I talk to, on a very regular basis. And it tends to be friends that have been with me for a very long time. It's a smaller circle. It's an older friendship. And even, the community that we live in here outside DC, it's very few that have kind of come in the walls, I guess I'll say, and that I have either had the bandwidth to embrace or, you know, 10, things need to line up right -- that my kids interested in their kid, we're kind of on the same wavelength. Skipper: Right. Jen: You both don't work in offices, you know, I mean, the algorithm to make a friend when you're 42 is very complex. But it's real, that I really think less is more in a lot of ways in the world. And the hubris of the American innovative spirit, is the opposite of that. And so I would like to be a voice to reclaim a smaller, more conservative, reasonable, but full to the brim of fulfillment version of a business. Skipper: Yeah. Plus one to that. I think I love that you used the word hubris to describe the American entrepreneurial spirit, because there's a lot that's loaded into that and that idea of success, and that it needs to look and feel a certain way, even if it's a sham that exists on social media. Jen: Totally. Yeah, well, that's another thing, right? Like your follower count. This is, you know, a parallel conversation. But I have a memoir that I wrote, I was very sick in 2016. I wrote a memoir about it, and it's ready to go. You cannot get into the Big Five publishing industry. It is so hard. And I'm like a pretty networked, savvy gal. And so I had to readjust my strategy this year, and instead have met all kinds of really interesting people at small presses, and indie presses, people who do not expect that their full time job would be a writer. Like, they have a different job. And then they write on the side. Like, my neighbor is a poet who works at the State Department. What? That's so cool, what a weird combo, right? Oh, just stuff like that. Skipper: Yeah. Jen: And again, like the openness, the creativity, the community spirit with some of these smaller presses, is chest way more interesting to me than the song and dance and beyond that you have to do to get like agents to represent you with these larger publishing houses. And may it be so, you know, maybe that happens to me. And that would be as long as I felt like that was the right fit. Maybe that happens one day, but it's just another echo of the same thing, you know, which is that smaller is more intimate and more authentic. Skipper: Yeah, I love that. You've mentioned your book, and I was hoping that we would talk about it a little bit. So whether it's about your book or your work with Plucky or something else. Is there a topic that we haven't gotten into that you want to get into? Jen: Yeah, I'm gonna negate all those and step back a minute into some of what we were just talking about, because I think there's a level we didn't get to that would be valid to talk about. Skipper: Awesome. Jen: And this maybe the audience for this is other coaches or therapists even but as a coach, I have to admit that there is a limit to what I can do for someone. I kind of said before that depending on the content of what comes up in a coaching session, there are sometimes things that are very heavy at the end of the day, especially if there's a pattern like these things happen in certain weeks. It's like I hear the same thing over and over again, there was a week last year when like, the behavior of CEOs, even at small companies was so preposterous to me Skipper, I just shut my laptop and went and rage baked for a couple hours, because I couldn't even handle what I was hearing. And as a coach, I can't blow up in the moment. I mean, I can say things like, You are fucking kidding me. What did he say, you know, I can say that. But ultimately, I then have to wind it back down. Because it's not about me in that session. However, the accumulation of that over the course of a day or a week can have a real effect on who I am and what I believe about the world. So it's important for me -- and again, maybe other coaches or support people -- to rebalance myself, I guess I'll say. And sometimes it necessitates me changing who I hang out with. Like, I've noticed that this year by and large, I am having coffee more often with women, or women who want to start their own businesses. Now this is not clients, right? We're just talking about, like, what do I do with my precious social hours here? And it's not to leave people out. But there are certain points of inflection where I'm like, I don't even want to see any CEOs for coffee right now. You know, like, even though I know, some and for sure, like it could be social. And I could ask about their kids and all that sort of stuff. And I just say that because I am not immune to what I'm hearing about. And there's only one time I cried during a coaching session -- and that was just the empathetic weight of the stuff that was coming out. I am not HR, I can encourage for folks to go to HR, but I ultimately can't. There's a limit to my control, like I said, and so I think that's just another aspect of coaching that again, nobody talks about, because we're the wise gurus on the tops of the mountains. But when people say real shit to you, it is an honor to hear it. And it's so precious. And it also does stick with me. So, yeah. Skipper: Understanding that we could, we've already been talking for over an hour. Jen: Sorry. Skipper: We could -- it's all good. No, no, please don't apologize. We could keep talking about this, I think, for another hour. But I think we're at the point where we're gonna wind down -- Jen: Pull it together. Skipper: Exactly. And we have some closing questions that -- I have some closing questions, isn't the 'we' a funny thing? Jen: I love the 'we'. Skipper: When you know that other people are listening? Jen: Yes. Skipper: But it's really just me and you talking. Jen: You and the listeners? Skipper: Yes, that's right. I have some closing questions that we ask on the show. Is there a significant lesson that you wish you had learned earlier in your life or your work? What would that be? Jen: This is a personal version of it so I don't know, obviously, other people may not have the same thing, but that I'm smart enough. Skipper: Say more about that. Jen: That I am a smart person. And I didn't go to an Ivy League school and I don't have an MBA, and I didn't get series a funding. But the work that I do in the world is good. And I'm good at it is really what I mean. It's also altruistic, but I'm talented at it. And I think it took me a long time to feel like I wasn't just sort of convincing people to pay me to talk, like both of us talk but the reality is, I'm not talking. I mean, I'm listening, and I'm asking questions, and sometimes I'm making a tiny reference to my own life, but that I have real talent. And it came up in a really funny career shape. But it took a while for that to sink in. And for me to not feel false. Skipper: Yeah. Is there something that in your life, whether it's a book, a TV show, a podcast, a movie? Is there something that you're super psyched about, something that's really igniting your enthusiasm? Jen: This is so random, but I just watched this documentary called "The Andy Warhol Diaries." Skipper: Okay. Jen: I really did not know anything about Andy Warhol. I vaguely knew the Campbell's Soup cans as a thing. Oh my gosh, Skipper, I'm like ready to drive to Pittsburgh right now to go to his museum, the museum about him. What I took away from that show was, weirdly an understanding of how the decades like the '70s, '80s, '90s -- how culture shook out. I was born in '81. And I never really understood like the 70s seems so trippy, and everybody was like, hi all the time. And then the '80s were like Reagan. And I, I was like, maybe that's just because I didn't grow up in New York City. But now I can, like I came to understand what happened to art and what happened in politics a little bit more, and then definitely the AIDS crisis. And, you know, I was a kid growing up, so I didn't have that perspective on the history, it was too close to my growing up years. So I really loved watching that movie. And, of course, hearing about him, you know, pros and cons, but I loved the, like almost American history takeaway I got from that. Skipper: It's such an interesting thing when you look at it through the lens of an artist, and Andy Warhol produced art for a long time, and he had very specific philosophies about art, whether you agree with them or not, you know, we are products of our time and space. So that's really interesting, say the title of it. Jen: Again, it's called "The Andy Warhol Diaries." And it's based on his diaries that were published after his death, I guess he had his friend Pat take notes every day for his whole life with him. And I mean, it sounds like a whole project. But one of the coolest parts about it, is that they use AI, with his voice, I guess, like all compiled in there, and then they have it read the sections of the diaries. So it's as if he's reading it. I mean, it's kind of creepy. And you're like, Oh, God, this is kind of my dystopian nightmare, but it's also kind of interesting. Skipper: Right. Jen: So, I recommend it. Skipper: I almost imagine -- and I don't know a ton about Andy Warhol -- but I would imagine that he is a person if he were alive today, he would probably embrace something like that and be like, yeah, let's give it a shot. Jen: That's what they say. Oh, yeah. They were like, Oh, yeah. Andy Warhol would be really into this. Skipper: Yeah. So if you had an unexpected day off, and unlimited resources, ability to defy even the constraints of space and time? What would you do, Jen? Jen: I am between two answers. One is I would go somewhere for a long hike. Like alone. It's the kind of thing that on a regular Tuesday, I can't leave all the obligations, I have to go do it. So it has to be an intentional decision to run away, basically. And the other thing would be to learn a new language. You said space and time is fine. Skipper: For sure. Jen: Go, you know, live with a host family in the south of Italy, or wherever and just by osmosis, pick it all up, I would love it. I love learning new languages. It's the cutest and most fun. It's the only way to be a kid again because you're like, Do you prefer a bath or a shower? Like you can't say anything for, like, two years, you know? Skipper: Right, right. Jen: All you can say is, And you? Sandwich or soup? You can't talk about anything. But the meaning is there. And you know, there's a fully functioning adult behind the sentences. This makes it so funny. Skipper: For sure. That's such a great analogy. So the last question is -- and we'll link to beplucky.com and all the things that are in your biography, but -- are there certain places that people should look for you to find out more information about you? Jen: Yeah, there are two things that comes to mind. The first is the newsletter. So if you go to the website, and you scroll down, there's a place to put in your email and stuff. I send one newsletter a month. And I always tell a story in there. And I give a couple links for stuff that might be interesting for people who like to think about this. And the second is I am on Instagram -- I'm not on Twitter anymore -- and every Monday I make a little reel, telling everybody here's what's going on in my week. Here's how I'm prioritizing. Let me tell a random story. Skipper: Yeah. Jen: Hopefully, as people are listening, they realize, I think about work, but I think a lot about how it intertwines with life, too. And so yeah, if you just need a positive way to start your Monday, you might go check out my Instagram. Skipper: So you have your own Instagram, but then you also have your writer Instagram -- Jen: I have like 30. Yeah, it's so identity complexifying here. Yes, it's @bepluckster because beplucky was taken -- so @bepluckster is Plucky and then I have @jendarywriter, which is my writing one. Yeah, that's right. Skipper: Okay, okay, Jen, thank you so much for taking time. This has been a great conversation as I thought it would be. Jen: Thank you for having me, Skipper, and everyone listening -- Skipper is also a coach, so you could definitely call him if you need help. And you were like that lady's weird, but I'll call Skipper definitely. I'm gonna refer you, this my referral to Skipper. Skipper: That is very sweet -- and so on the podcast, even though I've done it for a few years now. It's actually only been the last, there's one episode that's out but I never introduced myself as a coach first. Oh, great. I buried it inside the intro. So that's actually a note that I have for myself. I may not be a really good salesperson, but then it becomes a self-fulfilling cycle. I know, yes, I'm not a good salesperson, but it doesn't matter. Jen: But you're smart. As we learned from my one lesson in this planet earth experience. I'm smart, same for you. Skipper: That's right. That's right. Well, thank you, Jen. I appreciate it. Jen: Thanks. Skipper: And thank you for listening to How This Works. We appreciate your support and would love it if you'd subscribe and leave a review wherever you get your podcasts. We're in our second season, and it would mean a lot if you could share the show with just one other person, highlighting why they should listen. You can find us online at howthisworks.show, that's four words with no dashes. Again, that's howthisworks.show. We're also active on various social media platforms. I hope you gained some valuable insights from today's conversation with Jen. I certainly did, and we'll talk again soon. [Outro music] Jen: Yeah, I speak French. And my kids never remember -- Skipper: Oh, right, French literature, right? Jen: And they they say like, Mom, do you speak Spanish? And I'm like, No, French, it's the word French. That's the language I speak. They don't remember. And we were on a train last weekend. And the guy that sat next to me is from Belgium. And anyway, I heard him speaking French to his kids. So I said hi in French, and we were off and talking. And my kids were looking at me like I was a robot weirdo. And they were like, What are you saying, Mom? Imagine your mom comes over. It's like, blah blah blah blah saying words you have no idea. And it came out of nowhere, and she has never talked to you like that in your life. And all of a sudden, like the aliens have taken over your mother to talk to the guy next door on the train. That was what they looked at me like and I was like, Oh, they're going to Florida and they're like, Oh my god. So, my monolingual sons were blown away by this extra talent. Skipper: Nice.