s2_e1.json

[{"role": "system", "content": "She’s a C-suite-level executive with 20 years of experience working in corporate finance. Earlier in her career, she stayed at companies for long periods of time. But in her last few roles, she’s been jumping ship as soon as the going gets tough. Is she leaving too quickly, or has she not yet found the right role?"}, {"role": "assistant", "content": "I’m coach AI. And this is Coaching Real Leaders, part of the HBR Presents Network. I’m a longtime executive coach who works with highly successful leaders, who’ve had a bump in the road. My job is to help them get over that bump by clarifying their goals and figuring out a way to reach them, so that hopefully, they can lead with a little more ease. I typically work with clients over the course of several months, but on this show, we have a one-time coaching meeting, focusing on a specific leadership challenge they’re facing."}, {"role": "assistant", "content": "Today’s guest is someone we’ll call user to maintain her confidentiality. She’s a C-suite level executive working in private equity backed companies and has over 20 years’ experience in corporate finance. She likes to fix things and she likes a challenge."}, {"role": "assistant", "content": "user is facing a problem. Earlier in her career, she stayed at companies for long periods of time. But in the last few roles she’s had, she keeps wanting to leave. And something about that just doesn’t feel right to her."}, {"role": "user", "content": "The challenging things for me is when I’m tasked, I get to fix things. And I get in there and there’s all these sacred cows. What I typically do is I tend to then devolve into this, “I can’t fix this. I can’t fix this.” So, if nobody’s going to listen and I can’t fix it, then I got to move on to the next thing, and where’s my next job coming from. And then I go into another fix, and then I find myself in the same situation. So, I can’t really cope yet. I haven’t figured out how to lean into the discomfort."}, {"role": "assistant", "content": "user, isn’t sure if she’s leaving too quickly, giving up or being a quitter, or if she just hasn’t found the right company and role yet."}, {"role": "user", "content": "What I would like to see is I would like to see myself able to see it through. I would like to be able to see through this role to a successful exit or a partnership, a company transaction, or a sale, and actually stick with it, not take my tequila shot and say, “I’m out of here.” But just to take my tequila shot and say, “Let’s start again tomorrow.”"}, {"role": "assistant", "content": "So, the question for user is, how do I see things through even when the going gets tough? Which made me curious about what her experience had been so far."}, {"role": "user", "content": "In the last six years of my career, I’ve moved into these executive type roles, primarily into a CFO roles at private equity backed companies. I really enjoyed these roles. They give me a chance to flex my work muscles and do things that I enjoy. But at the same time, I found myself in this pattern of when I hit a brick wall, then I just throw in the towel and say, “Okay. I’m moving onto the next gig.” And every time I say, “This is the one.” And here I am again. And I’d really like develop some skills to stick it out and find out what’s going on and why I’m leaving so quickly."}, {"role": "assistant", "content": "Okay. Got you. And so, in the first part of your career, what did you enjoy about those roles and what led you to stay?"}, {"role": "user", "content": "I think that in those two companies, every 18 to 24 months, I would go to my supervisor and say, “I’d really like to do X, Y, Z now, this project to work with this department.” And they’d say, “Okay, go and do it.” And I go and I get new activities, good accomplishment, good achievement. And then I go onto the next one. And it really was the reason I really left after the 10 year one was because I run out of places to go, run out of things to do. So, I said, “Well, let me see what else is out there.”"}, {"role": "assistant", "content": "And what led you to take more of these CFO at PE backed company type of roles? What led you down that path?"}, {"role": "user", "content": "I loved that it was a completely blank canvas, and it was like the company was in a little bit of chaos. And so, it mirrored my previous excitement at the other companies where there was something that really needed to be addressed, and I could go in, and I could roll up my sleeves and address it and get success for the company."}, {"role": "assistant", "content": "Okay. Got it. And has that been your experience in the different roles that you’ve been in?"}, {"role": "user", "content": "Primarily, yes. That’s what I see. If it’s not broken, then I don’t want the job. I like jobs that have some chaos because I like putting processes and procedures, and getting people on teams that they’re excited, and they feel like they have something to go for. I was a college athletes. So, it brings back that like, “Let’s go team.”"}, {"role": "assistant", "content": "And so, when you were a college athlete, what did that look like? What was your role on the team?"}, {"role": "user", "content": "So, by the time I was in college, you go from being the best player in high school to, I was probably the middle tier. I really took my role as I’ve said, “Well, I’m going to be the one that practices the hardest. I’m going to finish every sprint first.” And I spent a lot of time with my teammates saying, “Okay. Everybody gets a class. Let’s get places on time. Give it all you got at practice.” So, my role was always like, let’s get everybody moving in the right direction so we can win."}, {"role": "assistant", "content": "Mm-hmm (affirmative). And when things got tough there, what was your role as the team player?"}, {"role": "user", "content": "Well, when things got tough, my first year in, I quit the team. So, I said, “Well, I don’t like the way this is going. I’m just going to quit the team and just go right on to be a student.”"}, {"role": "assistant", "content": "And after you quit or left the team, then you had three or however many more years left of college. How did you feel about looking back at your one year basketball college career?"}, {"role": "user", "content": "Well, after first year and my coach asked me, “Hey, will you come back for a second year?” So, I came back the second semester of my sophomore year. I felt like it was the first time in my life in the classroom that I found like, I started to finally be rating success in the classroom. So, I said, “Okay. Well, let me go in this direction.” Because I played sports my whole life, and that was my focus. I’m like, “Well, let me go do the fun stuff in the scholastic atmosphere.”"}, {"role": "assistant", "content": "Okay. So, I didn’t mean to go to your basketball college career, but it feels a little familiar to what you said is happening on the work front. Because if I’m hearing you on the work front, it sounds like what you’ve experienced recently over the past six years is being somewhat of a nomad, in that some place seems exciting. You go there, it seems fun, then something happens, and then you say, “Not so fun anymore. Don’t like this. I’m moving on to the next.” And great for you, there always seems to be a next ready, right? Well, I mean, you’re crossing your fingers, but literally it’s happened six times."}, {"role": "user", "content": "It has."}, {"role": "assistant", "content": "So, it’s pretty good."}, {"role": "user", "content": "It has."}, {"role": "assistant", "content": "That’s a pretty good track record. Right?"}, {"role": "user", "content": "Well, I’m waiting for [inaudible 00:07:15]"}, {"role": "assistant", "content": "You’re way past the three times a charm."}, {"role": "user", "content": "I am."}, {"role": "assistant", "content": "So, or it’s, obviously you have something to add a value that people want, and it’s no similar to what happened with your basketball career in that you left the team, and then your coach came coming back and said, “Hey, will you come back?” Right?"}, {"role": "user", "content": "Right."}, {"role": "assistant", "content": "The question is, what drives you to the side to move on, one. And two, the challenge that you’re coming with is, how do you stick it out, even when things get “hard” or uncomfortable? And so, I’d like to ask you, why stick it out? Why is that even important for you? Why not keep moving when something doesn’t seem comfortable or right for you?"}, {"role": "user", "content": "It’s important for me to stick it out for a couple of reasons. Sometimes I want to see through the sale of the company or an acquisition of the company. So, I feel like I will get the company 80% there and I’ll say, “Okay, they can finish the rest without me. I’m going to move on to something more exciting.” There’s something I do question myself that I say, “Okay, I’m going to move on because this is uncomfortable.”"}, {"role": "user", "content": "And I think sometimes I want to stick it out to show myself that maybe for once I made the right decision. Sometimes I’m like, “Do I just have a really bad picker with jobs? Or I do I not have good coping skills?” I think I want to show myself that I can actually finish something that I’ve started."}, {"role": "assistant", "content": "So, talk to me about situations you’ve been in where it got you to the decision point of wanting to be like, “Peace out, I’m out.” What are the conditions in place that lead you to then say, “I’m at 80%. I’m going to move on to the next.” Or as Ariana Grande would say, “Thank you, next.”"}, {"role": "user", "content": "I love that. I think there would be maybe a couple of different things. There’ve been a couple of times when I’ve had a micromanaging boss. I was like, “I am out of here very quickly.” I would say a couple other times were places that despite my best efforts to ask the questions during the interview process, they were places that were looking for, 80 to a hundred hour weeks round the clock. And I said, “I’m not doing that.” Once I got in, I’m like, “I’m not doing that.”"}, {"role": "user", "content": "And the third, that was probably the one that probably sticks with me the most is that I’ll do these projects and get all these good wins, and I’ll get to the next project, and I might get a note or, “Hey, the company is not ready to do X, Y, Z.” Or, “Let’s do a different strategy.” Either, it won’t be the right time for the company or there won’t be the buy-in that I’m accustomed to getting. And I think I’ll say to myself, “Well, if there’s nowhere else for me to go here, then I’ll go and do it somewhere else.”"}, {"role": "assistant", "content": "Yeah. Yeah. Okay. Got you. So, there seems to be, at least from the conditions that you’ve spelled out, the micromanaging boss, which is an external condition that you don’t really have full control over, the 80 to 100 hour work weeks that you weren’t able to vet for in advance. And then there’s this third layer of you having had successive wins in your role at that company, and you’re ready for the next win, but then there’s a blocker or a staller that says, “No, we’re not going in that direction.” Right?"}, {"role": "user", "content": "Yes."}, {"role": "assistant", "content": "But you see like, “No, no, no, no, we should go in this direction because it’s another win.” And they’re saying, no. Okay?"}, {"role": "user", "content": "Yeah, that’s correct. And it’s really common in this space, the private equity space. Someone will call you every couple of weeks and say, “I have a new role. Are you interested?” So, when I hit that roadblock, I say, “Okay. Well, I can just go over here.” And I start to all of a sudden, I know when I go to LinkedIn and I put click the box, that I’m now open to recruiters, that for me is always that like, almost like a relapse, if you will, “Can I go? I’m ready to go again.”"}, {"role": "assistant", "content": "Okay. So, when you hit that box or when you start saying, “Ready to go on to the next.” What are your expectations going into the next?"}, {"role": "user", "content": "That’s a great question. My expectations are, “Let me go to a blank canvas, where they really need me to sort things out, because where I am, they don’t need me that much anymore.” I will say like, “I’ve tackled a lot of the things that they wanted me to tackle. So, now let me go to another place that now needs me again to tackle their projects.”"}, {"role": "assistant", "content": "“And so, they don’t need me anymore.” What evidence do you have that that’s the case?"}, {"role": "user", "content": "That is a great question. I’m probably telling myself that. I think usually I associate someone saying no to a project or, “We don’t need this project.” To saying no to maybe to me. And so, I’ll say, “Well, if you’re going to say no to me…” This sounds so terrible. It makes me look at myself like, “Really, you really need everyone to say yes to you all the time. It’s ridiculous."}, {"role": "assistant", "content": "It sounds like what you have identified as your success pattern or your success metric is when people say yes to you."}, {"role": "user", "content": "That’s all the point."}, {"role": "assistant", "content": "Or when you get the win, right?"}, {"role": "user", "content": "Mm-hmm (affirmative)."}, {"role": "assistant", "content": "Or even the way you described what your experience was in the classroom, when you went to college, you said, “All of a sudden it became fun because I was starting to excel academically.” So, you’re defining your own success as the wins, right?"}, {"role": "user", "content": "Mm-hmm (affirmative)."}, {"role": "assistant", "content": "The achievement. And look, there is nothing wrong with wins and achievements. We all want them. The question is, how closely are you identifying with it, so that when they don’t happen, you then translate it as, “Oh, if somebody is blocking my win, it means that they don’t need me anymore.” I can understand why you are where you are, because your whole career has been this constant, “Well, here’s a place where you can add value. And here’s another place where you can add value.” And it’s always associated with an achievement or a milestone, or something that needs to be fixed. And so, the question becomes as an executive, as the CFO, when that is taken away, then how else can you add value?"}, {"role": "user", "content": "Mm-hmm (affirmative)."}, {"role": "assistant", "content": "One of my favorite quotes is, we don’t live our lives, we live our patterns. In user’s case, she’s living the pattern of only being as good as her next win. It’s no wonder every time that win seems threatened, she’s out. So, if her goal is instead to see things through, even when a win is not insight, she has to break the cycle. But first she’s got to be honest with herself as to whether that’s really what she wants. So, I asked her just that."}, {"role": "assistant", "content": "I think there’s a season for everything. You’re just living one season and not willing to see the next. It’s almost like, you want summer, whatever your favorite season is. I don’t know what your favorite season is."}, {"role": "user", "content": "Summer is great one."}, {"role": "assistant", "content": "Okay. Summer is mine too. But it’s like, “Oh, summer is over, shoot. Here comes fall.” No, no, no, no, no. You know what? I’m going to go like, “I just want it to be summer all the time. So, let me resist that fall is coming and winter is coming.” And knowing that at some point summer is going to come again, but in the meantime, I’m like, “Oh, let me be out. I’m leaving.” Right? Not believing that summer is going to come again. Okay? And then I move to the next place and it’s like, “Oh, here it comes winter. Okay. Well, let me move again, right back so I can keep it summer.”"}, {"role": "assistant", "content": "And look, there are people who do that. These are the people who constantly are going from, I’m from New York, so like New York to Florida, Florida to New York, back and forth, so they can stay in summer all year round. That’s their choice. Okay?"}, {"role": "user", "content": "Right."}, {"role": "assistant", "content": "But they can’t say that and say, “But you know what? Gosh, sometimes I really would love to just experience winter.” It’s not going to happen. You got to make a choice. You got to stay in a place where it’s going to be winter for you to experience winter. Okay?"}, {"role": "assistant", "content": "So, I think the first place to start is, user, what is it that you really want?"}, {"role": "user", "content": "As I evaluate it, I do want to develop that skill on myself, where a winter will come and say, “Okay. Well, let me get through this winter and let me get to know what these people, myself, what we’re really made of in a time where it’s not so summery outside.” So, I do want that. I think I get so uncomfortable that I leave, but I’m also, it was easy five years ago because every job would say, “We’ll give you 30,000 more. We’ll give you 30,000 more.” And everybody would escalate it. And now I’m sitting at this top echelon. And so, and I’m an executive. And I don’t have a whole lot of other places to go, so I need to develop the skill to stay."}, {"role": "assistant", "content": "Yeah. Yeah. And what it sounds like is, for a while now, what has retained you are external conditions that would, I don’t even want to use the word comfortable, but that were good rationale to stay. Right?"}, {"role": "user", "content": "That’s it, rationale every time."}, {"role": "assistant", "content": "And after a while you check the box, check the box, say, “Okay. I’ve gotten the higher comp. I’ve gotten the title. I’ve gotten the nice office. I’ve gotten those benefits and blah, blah, blah, blah, blah.” But I’m still not comfortable. Right? Which tells you that that comfort level has nothing to do with what’s happening externally, it all has to do with you internally. Okay?"}, {"role": "assistant", "content": "And so, I want to go back to, what is it exactly that makes you uncomfortable? Going back to the, this when people say no, because it sounds like, and I don’t even think it’s just when people say no, when it seems like there is a barrier to what you define as success. What is uncomfortable about that?"}, {"role": "user", "content": "I think a lot of my career, I have almost felt like a salesperson, if you will, like a salesperson of projects. And I think it’s, I didn’t get the sale or I failed, I lost the deal. Or it’s, I really, really wanted somebody to see what it could have been."}, {"role": "user", "content": "And I think it’s, I’ll see a blank canvas and then I’ll say, “All the way to the end of what it looks like.” When the company is in great shape with good leadership, and this project is done. And I think it’s having to let go of what I hope would be. And so, instead of letting go of what I had seen, I just say, “Well, fine, just let me erase that. It doesn’t feel good. Let me go see a vision somewhere else.”"}, {"role": "assistant", "content": "Mm-hmm (affirmative). Okay. So, the source of much disappointment is when we have a grand vision of what could happen and it becomes our expectation of what should happen, and then it doesn’t happen. And so, what do we do? Right?"}, {"role": "user", "content": "Mm-hmm (affirmative)."}, {"role": "assistant", "content": "And your, what do we do? Is to say, “Okay. Well, then I’m just going to move on to the next, and see if I can make it happen there.” Right?"}, {"role": "user", "content": "Mm-hmm (affirmative)."}, {"role": "assistant", "content": "And then it’s, we go through the same routine. Now, I’m not suggesting in any way that you shouldn’t have a vision and that you shouldn’t have a sense of what you would like to see happen. Right? That’s part of your role as a leader in any company."}, {"role": "assistant", "content": "My question is how tightly do you hold onto that vision that when it doesn’t necessarily happen in the way that you envisioned it, your only option left as of now is to totally abandon it and completely move away from it."}, {"role": "user", "content": "I mean, I think there were two things that you said that really resonated with me. And that was when I see a vision of what could happen, I start to internalize it as this is what should happen. And so, I get really married to it. And then when it doesn’t happen, it’s this giant letdown. And so, maybe instead of holding it a little more loosely, like this is one of the paths that we could take, I look at like, this is one of one and that’s it. And I think something else that was an aha, was that I will leave. And the exact same thing will happen again. We hear so many times the definition of insanity, doing the same thing over and over, and expecting different results. I think I’m looking at my vision and getting so entrenched in it, that I leave and then it happens, and then I leave. So it’s, how do I adjust that vision to be an option, not an absolute."}, {"role": "assistant", "content": "Yeah. How do you adjust that vision? Because adaptability is really the muscle that needs to be built. And how do you create other options for yourself? Right? There’s an author and psychologist by the name of Dr. Shefali Tsabary, she articulates it in a really nice way, where she says, for any given situation, you really have three options. Option number one is to stay and accept, right? Option number two is you stay, but you change your response to the situation. Notice, I didn’t say change the other, meaning change the board, change the managers, change your response. Option number three is to do exactly what you’ve been doing, so it’s not a wrong option is to leave. You have excelled at leaving."}, {"role": "user", "content": "Yes. I can simply say I’ve mastered number three."}, {"role": "assistant", "content": "Right. Which again, I mean, I will tell you that usually is the one that’s really hard for people. Okay."}, {"role": "user", "content": "Right."}, {"role": "assistant", "content": "So, right now, if indeed you are motivated by being able to demonstrate that you can have longer tenure somewhere."}, {"role": "user", "content": "Yes."}, {"role": "assistant", "content": "If you were to stay, if you’ve reached that point where it looks like winter is coming, right? What are your options that would allow you to stay?"}, {"role": "user", "content": "I think it is probably sitting down with my boss, who’s the CEO. And I would say, “Hey, I saw us going on a trajectory. Okay. Now, that we’ve changed from path A to path B, how can I make myself the most useful? And what can I do to our future partner to make sure that we perhaps feed our highest sale price to that partner?” Or that I learn a bunch of skills within the M&A sector, I may not have learned because I jettisoned out so quickly, how do I take the next year and really learn a lot of great skills, so that I’m best suited. So, I mean, now that I talk that out, it makes a lot of sense."}, {"role": "assistant", "content": "Let’s take a step back here. Through our conversation, user becomes more and more aware of how her strong expectations for what should happen, drive her to leave when they don’t happen. There’s nothing wrong with having expectations, but when held as tightly as user does, it can cause tunnel vision rather than the openness and adaptability leaders need to see the options available to them. Now, that user knows she has choices, she can decide which move best serves her in the long run. To do that, I asked user about her sense of purpose. What is her why?"}, {"role": "user", "content": "My sense of purpose internally is to show myself that I’m able to grow and not just stay stagnant. I think my purpose with my team is to see an entire deal through. And instead of just investing in people’s lives for one year and then saying, “It was nice to know you. I’m out of here.” So, what I’ve cobbled together are all these really temporary relationships. It’s developing deeper connections. I think it’s gaining confidence of a board, “She took us all the way through an exit. She was here with us in the good times and the bad times. And she’s just somebody you can count on through thick and thin.” So, I think it’s really the personal growth and the deepening connections with other people. And I think particularly for me, it’s with the CEO that I wasn’t his fly by night, fix it on this consultant type role that left, and left it for the next person. But yeah, she was my right hand all the way to the very end."}, {"role": "assistant", "content": "Okay. So, what I’m hearing you really articulating user, is a redefinition of the type of leader that you would like to be."}, {"role": "user", "content": "Mm-hmm (affirmative). That’s right."}, {"role": "assistant", "content": "Okay. And again, no judgment on being the leader who is the, I think you said fly by night, but fix it, come in, fix it, and move on to the next. look, being the turnaround person. Right? But what I’m hearing you say is, “That’s what I’ve done and I’ve enjoyed it, but I really have a yearning to be the through thick and thin, “I’ll stick by you.” The long run. Stick by my team. Stick by the CEO. Stick by the board. Stick by the company to try to get it to where it needs to be for as long as I possibly can. It doesn’t mean for eternity, but for a long enough time. Okay?"}, {"role": "user", "content": "Right."}, {"role": "assistant", "content": "So, that’s what you’re pivoting to. And that’s what you’re saying, “Hey, you know what? After all these years in my career, and I’ve had multiple successes, I really want to try to be that leader.” Then you need to align yourself with that vision of what you have for you as a leader."}, {"role": "user", "content": "Mm-hmm (affirmative)."}, {"role": "assistant", "content": "And so, there’s a notion of what you do in this moment, how you act in this moment, the decisions you make in this moment, the way you behave in this moment, inform how you show up in the next moment. Okay?"}, {"role": "user", "content": "Yeah."}, {"role": "assistant", "content": "So, if you take that and expand that to your leadership, if how you want to show up five years from now, is as the leader, who using your words, the leader, who stuck with it through thick and thin, how do you need to show up today, this week, and the next month, and the next six months in order to increase the probability that that’s what you will show up as in the long run."}, {"role": "user", "content": "So, I think for me now, when I go to a meeting and something isn’t adopted or there isn’t the buy-in that I’d like to see, I think instead of in the back of my head or the front of my head saying, “Lobby out of here anyway.” I think it’s to say, “Okay. Let’s focus on the things that we are adopting and let’s focus on those three tasks, and let’s start to really optimize and implement those, and see where those take us. And then after that, let’s see what’s next, what’s the next step that we’re going to take that people will want to go in that direction.”"}, {"role": "user", "content": "And I think it’s instead of going to the staff or some of my smaller groups and saying, “Well, I didn’t want to do this. So, we have to figure out what that means.” I think it’s, instead of taking that mentality, it’s saying, “Okay. Listen, the great news, we got buy in on three or four things. Okay, let’s start attacking this head on.” And it’s looking at the 80% and 90% wins and diving head deep into those instead of sitting with that 10% and saying, “I’m out.”"}, {"role": "assistant", "content": "Right. I mean, I think that it’s very interesting that when you said it, because you said, when you’re in those meetings and you hear the like, “We’re going in a different direction.” Or, “This is what you’re going to do.” In your head, your mindset, the operating assumption is, “I’m going to be out in a year.” And so, because you have this operating assumption of, “I’m going to be out in a year.” Then you behave in a certain way, right?"}, {"role": "user", "content": "That’s exactly right."}, {"role": "assistant", "content": "You’re like, “I’m not going to pay attention.” Or, “Let me go tell my team, but I’m going to do it half-heartedly.” So, I would be curious if your operating assumption, whenever you hear something that is contradictory to what your vision of success or where you thought you should be going with the company, if your operating assumption, instead of it being, “I’ll be out in a year.” If you shifted that to, “I’ll be here in a year.” What difference would that make?"}, {"role": "user", "content": "I think the difference is instead of disregarding it and checking out of the conversation, if it were, “I’m going to be here in a year.” So, while we’re not going down X path, we are going down this alternative path. So, what am I going to do to make sure that this alternative path is the best it can possibly be for the financial health of this company? And whomever we sell to, how can I make sure that I’m all in on this alternate path?"}, {"role": "assistant", "content": "Yeah."}, {"role": "user", "content": "So, I think you’re right, it’s a simple phrase. Instead of saying, “I won’t be here in a year.” Saying, “I will be in here. So, what does this mean that I’m going to do to make sure I do it right?”"}, {"role": "assistant", "content": "That’s right. That’s right. And underlying it is, how much commitment are you willing to give it today? Now, it doesn’t mean it’s forever. Notice, I didn’t say, what if you’re here in 10 years? I don’t want to stretch you too much. Right?"}, {"role": "user", "content": "That’s a bit much."}, {"role": "assistant", "content": "Let’s start with baby steps. But if it’s a year, and even though you’re not… Who knows what’s going to happen in a year? We don’t know. But our assumptions or what we think about it, help drive again, what’s the next step we take forward? And all we can look at is, okay, so that if you’re right now like, “Okay. I’ll be here in a year. So, what am I going to do next?” And then the next time something happens, you ask yourself the same question. And you ask yourself the same question until maybe one day you’re like, “You know what? I’m not going to be here in a year.” Right? But get into a practice of at least asking both, right?"}, {"role": "user", "content": "Yes."}, {"role": "assistant", "content": "What are the different scenarios? Rather than staying stuck in this automatic exit strategy before the going gets really, really tough."}, {"role": "user", "content": "Yeah, I do. And I think reminding myself, just because my personal focus is to grow some roots, and maybe roots look like two to three years in private equity. But I think for myself in that meeting, when I say, “I won’t be here for a year.” It’s telling myself, “Yeah, but you’d be at another board meeting.” And you’d be saying, you wouldn’t be there in a year either, because you’d be at the next board, and you’d say the same thing. So, if you want to get out of the cycle and instead of saying, “I won’t be here in a year.” Saying, “I am going to be here and what am I going to do? Because this is going to be different than before.”"}, {"role": "assistant", "content": "It’s also a lesson of how do you reach this intersection between what is your individual purpose, right? And commitment to self, which you absolutely need to have. And what is the organization’s purpose or the organization’s purpose, the company’s purpose and your commitment to the company? And when you are particularly in a leadership position, it is very unsustainable when there’s not an intersection between the two. And then you have to ask yourself, “Okay. What still keeps me locked in?” But it’s going to change. It’s no different than a relationship"}, {"role": "user", "content": "But it’s going to cycle in and out of… I think back to the company that I did work at for 10 years, I think back to in a three-year period, there were some 50 year awards for people that have worked there for 50 years. And they started when they were 15, and here they were in their mid sixties, retiring. And I remember thinking like they spent all that time here and all they’re getting is this card and this cake. And I thought, “I am not going to be sitting around for a card and a cake.”"}, {"role": "user", "content": "And I think it’s really, like you said, I over-indexed on, “No, I’m not going to do a card and a cake.” But now I have to tell myself, “Look, you’ve gotten where you wanted to go. You wanted to do C-suite roles.” And I think for me too, is now I’m leading groups of people that I really care about. And what does that saying about me? That I’m not emulating it all for them to put the company’s goals and strategies even into their purview. And if I want to model these things to find that intersection, that’s really poignant to me."}, {"role": "assistant", "content": "Yeah. And look, I mean, yes, it’s very endearing to say, “What am I emulating to others?” But I would suggest you really start with, what are you emulating to yourself? You’ve shown a really great track record of user as being true to yourself in terms of what’s important to you. I love it, when you said, “I’m not going to stick around for a piece of paper and a piece of cake.” Right? That’s not going to work. At least, give me the watch. Right?"}, {"role": "assistant", "content": "So, you’ve been very true to herself. And I don’t think that necessarily changes in this notion. I think again, I think what you haven’t explored is what does it mean to be true to yourself in these circumstances? What does it mean to be true to yourself when what you want is to stay?"}, {"role": "assistant", "content": "So, let me ask you a question. Let’s just imagine that this current gig you’re in, let’s imagine that you’re there two years, three years from now, let’s say three years. How would you define success three years from now for yourself? And the conditions are, you’re still, you’re there. Right? So, what would success look like?"}, {"role": "user", "content": "Success for me would look like I can have high performing teams and some deep industry connections that lasts. That I have a longer term bond with my CEO. The thing that keeps coming to my mind is success to me is when something goes wrong, I don’t say, “I’m out of here.” It would say, “You know what? I’m not the shiny new penny here anymore. I’m not impressing all the people anymore. I’m just here being a Steady Eddie. And it’s really working for me.”"}, {"role": "assistant", "content": "And have you had other times, whether it’s work-related or not work-related in your life where you’ve done that effectively, meaning it was difficult and you still stuck with it?"}, {"role": "user", "content": "Yes. I would say that I have had that in my marriage. Obviously, it does always go right. And you want to move here, I don’t want to move here. These kinds of things. And I would say in one particular job where I was there for 10 years, there were times where they like, “This won’t work.” I have done it a couple of times with the success."}, {"role": "assistant", "content": "Yeah. When you stuck with it."}, {"role": "user", "content": "When I stuck with something and been able to stay for the long haul. And it felt really good. In relationships in the beginning, it’s like, oh, you’re falling in love. And you want to stay on the phone all night, and say like, “You like the color blue? I like the color blue.”"}, {"role": "user", "content": "But I always say, I wouldn’t trade the deep into the double digit years of a marriage for just knowing someone, forgetting them, for someone being able to look at you and saying, “I’ve got you.” And I always say, but I think in work, that’s what I’ve done. I’ve gone for all these first dates."}, {"role": "assistant", "content": "Yeah. You’ve gone for all the first dates. I mean, gosh, wouldn’t we all have that."}, {"role": "user", "content": "Well, yeah, and I think that’s become my default is like, swipe right. Somebody will love me for a year."}, {"role": "assistant", "content": "I love it. Swipe right. Right. So, I mean, you have lived the fantasy. And good for you that it’s lasted so long. And it’s not to say that you have to go through difficult times. That’s not what this is about. It’s that we also don’t want to live in a fantasy. We want to live in reality. And the reality is there are going to be good times, “good times.” They’re going to be “bad times.” I don’t even want to say good or bad times. It just is the nature of how companies run. Right? There’s going to be, business is cyclical just like nature. I mean, we talked about the seasons, just like the seasons. Right."}, {"role": "user", "content": "And it’s like earning seasons. You have good earnings, you have bad earnings."}, {"role": "assistant", "content": "You have bad earnings. Do you calibrate who you are and what your success is based on the seasons of what is happening externally from you, or do you calibrate it based on what your own north star and what it is that you want and desire, or where you see yourself in the moment, or for the foreseeable future? Right?"}, {"role": "assistant", "content": "Something that you’ve said user, over our conversation is that what also attracts you and really charges you is the ability to continue to learn and to grow. And you even, when you talked about marriage, you said, “I wouldn’t trade in the years for the ability to see somebody.” And that person to see you and to be able to grow with that person, and for you to grow in that relationship."}, {"role": "assistant", "content": "And there’s something to be said for any type of relationship, whether it’s with a company or whether it’s with a person that the true measure of success is not necessarily in the longevity of it, it’s in your ability to grow, right? And in your ability to continue to evolve as a leader, evolve as a person, so that you’re contributing to yourself, but you’re also contributing to others. And how we define that growth is what’s critical."}, {"role": "assistant", "content": "You’ve defined that growth as a series of first dates, the transactions. And all we’re talking about here is it may be time for you to redefine what growth looks like. My guess is if you’re redefining your growth as being able to see something through, being able to nurture the connection, being able to model over the long-term to your staff, that a natural outcome of that will be your desire to stay. So, not necessarily making the staying the longevity, the 10 year cake and plaque, the milestone. That’s not it. It’s based on what you now see as your purpose as a leader, your growth as a leader, does it make sense for you to stay?"}, {"role": "user", "content": "Mm-hmm (affirmative). A hundred percent. A hundred percent. I mean, I think that’s right. And I think it really, it makes a lot of sense when you say, the way I’ve been doing it, it’s not a bad thing. People make careers out of that, but because I want different, then I have to think different, and see myself different."}, {"role": "assistant", "content": "Yes."}, {"role": "user", "content": "And that’s to say like, “Okay. It’s time to get a different mindset because I want personal growth and I want to grow into this kind of leader.” And that’s what I want and I’m going to do it."}, {"role": "assistant", "content": "So often people are stuck with this question of, “Is it time for me to leave?” They stay in situations that don’t feel like a good fit or don’t fulfill them. Here, user faced the opposite issue, when is it right to stay? And more importantly, how do I stay when it feels like I’m in the thick of it? But at the end of the day, it really comes down to the same core issue, asking yourself the same questions, what do you want? What kind of leader do you want to be? And how do you align your decisions and actions with that? Okay. Only when you take a step back and uncover what really drives you, and where you want to be driving towards, can you discern whether it’s time to stay or go regardless of the season."}, {"role": "assistant", "content": "That’s it for this episode of Coaching Real Leaders. Next time."}, {"role": "assistant", "content": "Thanks to my producer, Mary Dooe, music composer, Brian Campbell, and the entire team at HBR. Much gratitude to the leaders who join me in these coaching conversations and to you, our listeners, who’s sharing their journeys."}]