You Betcha She Did! Life Advice, Business Tips for Rad Women Entrepreneurs, Leaders, Coaches and

63 | Nurturing Leadership and Overcoming Adversity: Crucial Insights from Coach Jen Dary

• Ladies First Digital Media Company • Season 4 • Episode 63

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What if the challenges you encounter in life were the stepping stones to your greatest personal and professional triumphs? That's precisely the inspiring reality of our remarkable guest, Jen Dary, the guiding light behind Plucky. As a leadership coach to professionals from the world's leading companies, including Google and the New York Times, Jen's insights into the work culture, remote work, and relationship-building in a remote environment are unparalleled.

The conversation takes a heartfelt turn as we delve into the personal side of our formidable guest. Jen graciously invites us into her world, shedding light on her journey as a parent entrepreneur and how she strikes a balance amidst the changing dynamics of work, especially in the wake of the pandemic. As a brain tumor survivor, her perspective on mental health is deeply enlightening. And then, we segue into a vital aspect of professional growth - mentorship. From making a strong first impression to approaching the mentorship relationship, Jen's wealth of knowledge is sure to leave you inspired and equipped for success. So, gear up for an episode that promises to challenge your notions of leadership, mentorship, and overcoming adversities.

Connect with Jen Dary:

  • More at beplucky.com
  •  https://linktr.ee/bepluckster 
  •  IG: @bepluckster 
  •  @jenniferdary @beplucky on socials

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Speaker 1:

Did she really do that, you, betcha? She did. Hello, and welcome back to another episode of you, betcha Sheeted the podcast where female entrepreneurs, leaders and change makers share their wit and wisdom. I'm your host, raina Burkicki. Today, my guest is Jen Derry and she is a highly sought-after leadership coach, entrepreneur, brain tumor survivor mom and a host of a podcast called Be Plucky, and in her business, she coaches CEOs, entrepreneurs and leaders at every level to create healthy work dynamics. Who doesn't want that right? And a better work life for all humans.

Speaker 1:

A lifelong people person, jen started Plucky in 2013. They are currently celebrating their 10-year anniversary. She started Plucky in response to some serious soul searching and has empowered professionals at over 200 companies, including Google, facebook, slack, code for America, the New York Times and many more, so that is some serious client base. Jen also launched her own Be Plucky podcast, with a focus on mentorships and featuring a cast of professionals who shared their experience and insight. She has shared her expertise with the Wall Street Journal. It has guested on multiple podcasts, including the Harvard Business Reviews Women at Work. So, jen, welcome to the show.

Speaker 2:

Thank you. I'm so honored to be here. I love the whole vibe and everything about what you're putting out in the world. Yeah.

Speaker 1:

Well, thank you for that. I want to start with the word plucky. I love that word. It's not a word you hear a lot, so tell our listeners like what does it mean to be plucky?

Speaker 2:

Well, the original part of the story was that when I had my first son, it was kind of this opportunity to figure out what the hell am I doing with my life, yep, and it was like do I go back to work full time? Do I stay home full time? That wasn't really an option, but that was when I decided to start my own thing and I was trying to figure out like what would the name be. And fasauruscom is really helpful because you just put in a bunch of words that you're thinking about and plucky came up in the sentence that the example was R2D2, the plucky little robot, so that's from Star Wars. And I was like plucky, that's such a good word. Nobody ever says that anymore. And so it just felt like it fit. It fit my personality at that point. It fit like all the things that I wanted to be true in the world and the perspective I felt like having a fulfilled life would invite. And I couldn't get pluckycom because of the damn tiny tunes.

Speaker 1:

Oh, interesting.

Speaker 2:

So I had to get be pluckycom, which worked out just fine anyway. But yeah, other than occasionally people thinking I have like an eyebrow threading business, it really Sorry that's funny.

Speaker 1:

Yeah, generally works. Never thought about the eyebrow aspect, but that's that's kind of hilarious too. So you do a lot of work. You know coaching leaders, managers, entrepreneurs. Is there like a general theme of advice that you feel like everybody needs, or like what are some trends you're seeing in that realm these days, post COVID?

Speaker 2:

There's always a lot right. I almost feel like I have like an ear to the universe sometimes because I talk to so many people and I am able to hear well, to use your word trends, but like patterns, almost right, and what's kind of coming across. And I think lately you are seeing people who have had taken new jobs, let's just say, within the last two years, and the rate at which they are able to build relationships with others in a remote company is slower. And I'm like all for remote work. I think it's great and people can live different places, especially with different financial means, and work for different organizations.

Speaker 2:

But lately some of the maybe I'll say like trust between colleagues or peer relationships or anything outside of like a here's the meeting, here's the agenda, here's what we're doing. So any of that more casual relationship building isn't really present, it isn't really happening as easily, and so it makes it a little more intimidating to reach out to someone to ask advice or to get clarification. The bar is a bit higher in terms of just hey, does anybody want to hang out and have lunch over Zoom, especially for a new employee who happens to be coming in without any network there, and I think people are thinking about that more and also there's not an obvious solution to it.

Speaker 1:

Yeah, yeah, I never even thought about that the whole aspect of remote work and not being able to forge relationships really easily, but that totally makes sense. Yeah, there's not an easy solution, but those work relationships are pivotal, key to brainstorming and, like you said, trust is a big thing. So is that something you find a lot of companies are reaching out for help on, or some solutions?

Speaker 2:

Yeah. So one way that it shows up would be in a one-on-one coaching relationship with someone who has sought me out to work together and we might talk about this being like a sticking point for them, that they don't really have enough connection with people. So then we might sort of problem solve there and in what ways could they develop relationships with people they don't know. But the more recent one just this week even.

Speaker 2:

I work with an organization who has like an all hands once a year. So once a year they all get together, which is awesome and honestly pretty expensive for a company to fly like 50 to 100 people all to the same location and put them in a hotel and whatever. But they get that one time a year, which is obviously great, but it's only one time a year. So I am in this capacity, teaching actually a couple classes within that company and as a total random byproduct of that, the folks are getting to have relationships with folks in other departments whereas they normally wouldn't be in the same meeting space or zoom call right. But because they're all learning management or, in this case, leadership skills from me in this class, it's like this random byproduct which is a benefit to them, right To cross, pollinate and folks working across lines and you know just to. Oh, we have that in common. That lady, we were in class together with that lady. So, yeah, it's this random new thing that's showing up as a benefit to offering a class, for example in house.

Speaker 1:

Yeah, yeah, people get to connect and share that experience together, which is that's so important. I want to rewind a little bit and, if you don't mind, I want to hear a little bit more about your brain tumor experience, like what you went through and you know the soul sort of team that happened after such a big life event.

Speaker 2:

Yeah. So the long story short is that in 2016, so my sons were three and eight months and plucky was about two years old I was having a lot of random symptoms None of them seem to match up headaches and eye stuff. And all this Everybody kept telling me you're a young mom, you're stressed, you run a business, all that and eventually I had an MRI and we found a really large, like lemon sized, brain tumor.

Speaker 1:

Holy cow.

Speaker 2:

So that was like not the plan, never saw that coming. I was very lucky knock on wood that it was a benign tumor. So I had brain surgery. Two weeks later they got it out. You know I closed plucky for the time being while I needed to have that happening. And then recovery and the health journey has mostly been, you know, positive up and up. But now I do have seizures and there are other things because your brain really doesn't like when you go in there and mess around in your skull, really doesn't love that. So there are definitely like there is some fallout medically for me, although I haven't had recurrence. So that's great.

Speaker 2:

And I actually just finished writing a memoir about this. It's called I believe in everything and it's about that story and how do you come out of that and parent differently and run a business differently Kind of the things that you're alluding to, which is what is the outcome, what is the takeaway? Or it's maybe a little too mathy, but just sort of like what is the invitation to change after something so harrowing? I don't know. In short, I was like screw it, let's do it, yeah, so like what is that? Like we have walked up to the death line.

Speaker 2:

What else is more stressful, right? So, like I started a manager training program called so Now You're a Manager, I'd always had the idea I find those like screw it, we're doing it. Got a location in New York, threw it together and I'm now on the 27th cohort of that program, so I've taught it so many times now. I invented some products over here and then Again it just permeates into all things. I know you're not a parenting podcast here, but certainly the way I parent my kids, both in almost like a resilient way that I know they'll be okay in certain ways, but also an emotional way I can handle a lot of things.

Speaker 2:

and then I just dropped my kids off for back to school two weeks ago and I definitely cried on the way home.

Speaker 1:

Not because I was like my kids are growing.

Speaker 2:

It was more like I'm so lucky I get to still be here. That circle comes back with all those graduations, birthdays. Like I'm a mess on all those things, mostly out of gratitude.

Speaker 1:

Yeah, I love that though. Thanks for sharing that. I had a good friend who a similar story. Her husband in 2020, got diagnosed with a brain tumor too, and they didn't know where it came from. It was benign, but the whole surgery and the seizures and all that stuff and definitely looking at life differently after that, I'm like I get that we should all embrace gratitude, but I love hearing these stories because it's a good reminder to just live in the moment instead of thinking of the future in the past and getting trapped in those areas.

Speaker 2:

I mean it also affects so many things that I didn't predict. Actually, tomorrow I'm about to fly to the UK for almost two weeks and I'm going on a writing retreat and doing some stuff like that. I had options. My husband and I, long story short, had decided each of us should take a really cool trip this year. Awesome, he went to Japan in May and I had again a lot of flexibility. Where did I want to go? I found myself so reticent to pick what my option would be. I've lived in Paris. I got my master's over there. I've lived in Europe before.

Speaker 2:

A big part of this that I finally figured out is that what if I have a seizure? What if I'm in a country that is in English speaking? Let's say, what if I lose my seizure meds? All this stuff, as a 42-year-old, is real different than when I was studying abroad, when I was 22 and 23, where I was like whatever, let's go and train to Italy, exactly. And now I'm just a grown-up in certain ways, and so I never really thought it would affect solo travel. But yeah, it's another surprise, and I kind of assume that through the rest of my life there will be moments that keep coming up that remind me oh, different ballgame. Remember that.

Speaker 1:

Yeah, yeah, yeah, and there's nothing wrong with that. You just embrace different seasons of your life and what you need to work through at that particular moment. Well said, yeah. Well, actually, a lot of our listeners are I mean, it's mostly women, but they're a lot of entrepreneurs, a lot of parents, working parents as well, and what are some of the biggest challenges that working women especially face? I feel like moms in particular. It's just really hard to find the balance and stay true to who you are without losing yourself. I mean, what are your thoughts on that gigantic topic? How many podcasts episodes should we?

Speaker 2:

record right Irina, 9,000, everyone. This is pivoted to the new podcast. Well, I will say that you just mentioned that Plucky just turned 10. And I said earlier that I started it when my son was almost one. So I have never really been an entrepreneur without being a parent and I have almost never been a parent without being an entrepreneur. So that kind of has always been true and therefore I have always been insane. It has always been a balancing craziness, but to the point where sometimes I wished I had a boss to kind of set a boundary, like I wished that I could say dude, I got a meeting till five, you're doing whatever Aftercare at school or something. And because there's not a definitive bad cop, so to speak, in my life for work, my flexibility while it is completely great and I love the ability to go help at school sometimes and help with PTA, it also means that I am tired very often, because I don't necessarily hold that line for myself. So I would say that, to use your word from a minute ago, season.

Speaker 2:

There have been seasons of being an entrepreneur where I was more a parent and then seasons where I was more an entrepreneur, and that has kind of just been negotiated over the last decade.

Speaker 2:

This past year, I think, things evolved a little bit, where I also started carving time out for writing and, like I said, I wrote a memoir and I'm currently working on a novel and what I realized is that Plucky had been my only almost like venue or channel to be more than a parent, and so it absorbed a lot. It absorbed like OK, cool, like I'm a mom over here and then I'm Jen over here, and Jen was synonymous with working. And just this last year I have been able to separate that as, like Jen who runs Plucky and Jen the writer, and I don't know how fast people can get to that. For me, again, it took 10 years, but it is so great to not overload my entire individual identity on my work. Yes, that might be sometimes. You know, one of the Achilles heels of entrepreneurs who are also parents is that you kind of end up with this binary I'm either parenting or I'm working on my business.

Speaker 1:

I know Exactly, Because that's like another kind of baby you know, yeah, I know, and then you don't have any time for those other parts of you that exist but that need to be nourished. And you, I feel like I'm kind of at that same spot too, where I either been a parent or I'm working on my business and I'm ready for more. I'm ready to have more of me Free, you know, I know, I know, and it's like it was fine before like I said, it was a season but now I'm kind of I'm almost feeling like desperate to claw out of that and have some other interests.

Speaker 2:

Yes, and I would say that, if I listen, even underneath my own words, I'm like coaching myself here. But like I, you know, the only way I found to make space for another part of myself was to assign it a project right. So, like writing, and sometimes, if you can't just be like I'm enough, I'll be spending one day a week on myself, like for me that is too slippery, I'll end up doing laundry or I'll end up, you know, like guilting myself into some kind of exercise routine or like whatever For me. At the moment I'm parking that through a writing project, which I'm not going to be too mad at myself for it right now. But for people listening, if they're having a hard time or some of what you're talking about, there might be a project that is not work related, that makes you $0, that you just kind of do because you're really drawn to it. That might be a safe space also for you to feel more yourself. That is outside the you know bounds of parenting and working.

Speaker 1:

I like that this kind of goes along the same lines of this conversation. So, you know, like during COVID and then the rise of remote work and just the whole dynamic of working, the way we do work, how we think about work, work-life balance, has been shifting, I think, in a lot of healthier ways. You know, bigger focus on mental health and be more flexible, which is good. But you know, do you feel like companies want to see this trend continue or is there some fallback happening where they want to kind of bring it back more to the old days? What are you noticing out in the world?

Speaker 2:

Oh, it's such the big question, right? I mean, my general take on all these things is you nobody's going backwards Like you have opened the box.

Speaker 1:

Pandora, Pandora welcome.

Speaker 2:

So all of this sort of like, reticence, or like let's go back to the office, like, okay, there are certainly some practices like dentists are not working remotely, like what are we going to say? Right, yeah, I guess robots, maybe one day they will be able to, but for the moment, dentists be in house, okay, and so you know? I mean, the truth is that we can either look remote working in the face and say, given this new landscape, this new set of requirements, how do we maximize it? How do we set expectations differently? Somebody definitely will invent something that helps people build trust that you and I have just been talking about with space for that. I don't know if it's an app or a game or a lunchtime thing or a drone that drops the same thing off at everybody's house at the same time. I have no idea.

Speaker 2:

Somebody's working on that, clearly right, like it's a very innovative society. So I don't know. Instead of complaining about the problem, let's figure out some solutions and let's find some options moving forward. Now, that said, I think it can be bruising or just confusing for folks who grew up and got careers in a certain way and now find themselves in a very different landscape, and I have empathy for that, particularly for folks who are maybe north of like 50, 55 years old, who maybe don't really have the patience or hunger even to reabsorb a brand new look of society and to that end I would say some kind of support system, a coach, a therapist, somebody that kind of helped walk you through.

Speaker 2:

Well, who would you be? What would your new identity sort of be? To match the expectations until you wanted to retire or change or start your own thing. But yeah, we're not the first people to handle this. Definitely our grandparents. They worked at factories and they didn't. They did other stuff maybe. So evolution happens and things keep moving and I find that in general, like the stasis of like keep everything the same, or especially like let's go backwards in time to when it was really good it's, you're just punting, it's all coming anyway.

Speaker 1:

Yeah, you can't stop progress. It's going to happen, so embrace it Exactly. Yeah, tell us a little bit more about your podcast, be Plucky.

Speaker 2:

As I'm sure you encountered when you started yours and at some point people are like why don't you have a blog?

Speaker 2:

Then they're like why don't you have a podcast? You know, like it's like a thing, almost like a rite of passage. I feel like we're entrepreneurs at some point. And what I really didn't want, reina, is I did not want another obligation. So I was like I kept like people would say to me all right, I'll push it off. I'll push it off, maybe I should have a podcast. You know, because I'm not a podcasting company, it's not as significant of a project for me as yours. I decided, well, I'm going to do a season, like how TVs have seasons. So I was like let's do a season. And the theme of that season was mentorship, and that was because I had just launched a new product which we can talk about at some point later if you want. But anyway, one of the products is this mentor pack, and so it's full of cards with questions that you could talk about with a mentor, because people are like get a mentor, get a mentor.

Speaker 1:

But I know what do you do when you get one. It's so awkward, exactly.

Speaker 2:

You're like, hey, can you give me a connection? Like what? That is terrible, so anyway. So I made this mentor pack and then, as part of that, I was like, well, maybe with launch I could do a season of a podcast that would interview mentors. Yeah, so that I did eight episodes.

Speaker 2:

I picked a theme for each episode. Things like first impressions, performance reviews oh my gosh, no, I'm totally blanking. But stuff like that, right, career oriented, often, leadership vibes, how to fire someone, you know, like stuff like that and building trust and those sorts of things, the kind of stuff that people never know, they want to hear about until they see it and they're like, oh my God, first impressions. I've never thought about how I give a first impression, or should I do? I get a second impression, you know. So I picked people that I thought were really savvy with those things and that you know. That's what the podcast is. There's eight episodes, it's one season. If one episode speaks to you more than the other, you don't have to listen in order, obviously. And there's nothing that says I won't do a season two. In fact, I probably expect it in my life that I will, but I don't have that obviousness yet. So I'm waiting for the next kind of call, almost to figure out what that would look like.

Speaker 1:

I like that. Okay, speaking of first impressions, do you remember any of the advice that was imparted in that episode? Oh, not to put you on the spot, but yeah, I'm like I'm curious. What did they say about that? I know, I do want to know about that.

Speaker 2:

So the woman I was interviewing is Dr Evelyn Carter and she has been the president at a DEI research firm called Paradigm. So her first impression advice was kind of twofold. On one hand it was the notion of being intentional about your first impression. So in a job context that would be showing up looking like you're ready, you're prepared, maybe you've done a little bit of research, like, for example, today I listened to some of your episodes Like I knew I was meeting you and I did a little bit of recon about who you are, like, how do I show up and not look unprepared? So first impressions might involve intention and preparation ahead of time.

Speaker 2:

And then there's also invisible first impressions that people are noticing and some of that you can't really change and that might be something like patience or the way you cut people off Once it's pointed out to you. Then you might think about it. But there are probably some habits or just you know this goes deeper than just personality, but ways you interact in the world, privilege, other things like that that you don't always realize are coming along with you when you make a first impression. I thought it was really illuminating for her to talk about how you might prepare for something ahead of time, and then also how you might be self aware or more self aware about the other things you're conveying. You know, even when you walk into a Starbucks, or you know when you're walking around looking at your phone, like there are all kinds of ways that you're giving out passive data to the people around you. It was really good talk, actually.

Speaker 1:

Yeah, that makes sense, like it'd be. That's a great way to kind of be coached on it. Like you said, you don't even know you're doing these things, but then once it's pointed out, you're like oh yeah, light bulb ding, ding, like I need to change that or think about that again.

Speaker 2:

Yeah, or it also just is almost like the math behind why some things are working for you and why some things are not. And Well, anyway, we could get all psychological with it. But I think that self-awareness is, I always say, the number one quality I would hire for in another person. If somebody knows who they are and knows who they aren't and can show up, it doesn't mean they're not able to grow or learn or develop. It's just sort of like I'm not tricking myself into anything. So I'm going to be way easier of a person to manage because I know my limits and I will ask for help when I need it. That's all. Managers want for you to not be a black box all the time and they have to kind of figure out, based on your emojis on Slack, how the hell you're doing.

Speaker 1:

I hear that. I have one last question before we kind of wrap things up, and it goes along the lines of mentors and mentorship. I think that's something that all businesses should do, but I often feel that the mentees again don't know the questions to ask, and then the people who are the mentors have never really been properly trained as a mentor, so they're not really sure how to do that as well. Could you give us just a few tidbits for both of those positions the mentees and the mentors like just some guidelines or some pro tips to help us out with that?

Speaker 2:

Absolutely Well. Mentorship is a funny little echo or mirror of coaching, right? And so I will say that when I start working with a new client, I have them fill out an onboarding form and that has them tell me, why are we coaching, like, what are you interested in, and also, what would your goals be for coaching, and I keep track of that. After a couple of sessions, we check in Are we going in the same direction? And I think that kind of structure could be really helpful. For we'll just take the mentor section, if you're a mentor, to have some sort of simple basic form that you both fill out together and you set up those things, especially things like how long is this mentorship going to go on? How often will we talk? Will it be in person? I mean mentorship's like some of them just never die and they're still alive, but people just keep canceling and it's just like break up already.

Speaker 1:

I know.

Speaker 2:

It sounds horrible. It's like this is why nobody's mentor. I know it's like, oh god, I'm getting into a marriage, I can never meet. So I think setting up that structure, while probably feels really uncomfortable and weird, that's part of what is in this deck. Here is some basic questions for you to figure out, like in the beginning. For example, what are the goals in this mentorship? What would success look like for each of us? How often will we meet? How long are the meetings For what duration? Should we structure what we talk about each time? Or do you just let the mentee come and bring a topic? And how do you like to communicate? So, do you like email, text, slack, whatever? And then the endings card is kind of like a bookend for that.

Speaker 2:

Did we accomplish our goals? In what ways were we successful? Was there anything we were expecting from the mentorship that wasn't achieved? What are the mentees' next steps and what was the best part of this mentorship experience for both of us? So it's a little structured, but hey, man, welcome to the world.

Speaker 2:

A little bit of intention up front and intention at the end means a really well-rounded experience and if you can be honest with each other about well, I was hoping I'd get more network out of this, like OK, cool, I'll take that away as the mentor and as I encounter other people in the world that I think might be a good connection for you, I'll let you know. It's like OK, great, well, we both said the things and obviously outside of those two cards, the whole rest of the deck are things, questions to ask each other, like ask the mentee who or what do you compare yourself to? Most often, like these are the kind of questions that you can sink into and realize I am comparing myself to someone. Who is it? Why Is that appropriate? Should I get a new role model? You know all this kind of stuff and I think it just takes down the daunt at figuring out what in the schedule should we be covering.

Speaker 1:

Yeah, that's fantastic, just really great guiding steps to help both ends of that party get what they want out of it.

Speaker 2:

Yeah, totally.

Speaker 1:

Well, on that note, jen, thank you so much for being on the show. If you're interested in learning more about Jen Derry, her book, her podcast, I'll have all those links in the show notes, as always. Thank you for listening to you, betcha, she did. Don't forget to share the show with your friends. Don't forget your besties. Maybe your sisters, your mother-in-laws, they might need this information Until next time. Music].