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Being a Boss Isn’t for Everyone… Including Some Bosses | 19

24m 9s

Being a Boss Isn’t for Everyone… Including Some Bosses | 19

In this episode of Radical Cander, hosts Kim Scott and Russ Larroway explore the difficult but crucial question of whether management is the right career path for someone. They share Hunter Walk’s personal journey—from a successful product leader at Google managing 40 people to transitioning into venture investing—highlighting that management wasn’t fulfilling for him despite his technical excellence. The discussion emphasizes that only a small percentage of people are naturally suited for management, with most strong individual contributors being better off in non-managerial roles. Signs that management may not be right include a persistent preference for individual contributor work and a lack of genuine prioritization of team success over self-interest. The hosts present a candid checklist for those who have decided not to become managers: first, double-check the decision by discussing it with trusted mentors; second, tell your boss directly and only about the change to avoid team uncertainty; third, be open and honest about your rationale after the transition; and fourth, clarify your growth path—through deepening or broadening expertise—so you can continue to grow without management. The episode urges listeners to recognize that growth comes from learning, not just leadership, and to seek companies that offer clear career progression for non-managers. The message is clear: being a boss is not for everyone, and it’s courageous—and valuable—to make an honest, self-reflective choice that aligns with personal values and energy.

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(upbeat music) - Hello and welcome to Radical Canter, a podcast from Panoply and Gretchen Rubens' Audward Project about how not to hate the boss you have or be the boss you hate. I'm Kim Scott, co-founder of Canter Ink, former executive at Google and Apple, and CEO coach at Twitter, Qualtrics, and a bunch of other great companies. - And I'm Russ Larroway, also co-founder of Canter Ink and career-long operational manager across the Marines, Google, and Twitter. - So as you all know, we've been talking through our episodes about being a better boss and working better with the boss you have. But today we wanna talk about deciding whether you want to be the boss, whether management is a right thing for you. Maybe you're thinking about becoming a manager. Maybe you are the boss, but you're wondering if that's actually what you wanna be. - In today's episode, we'll share a story about making the decision that management might not be the right fit. - We'll talk about some ways to decide whether management is right for you. - And we'll wrap up with the candor checklist, our practical tangible tips for you. Let's get into it. We're really excited to have with us on the show today, one of our investors, Hunter Walk from Home Brew. For a little bit of background, Hunter spent some time at Second Life in a product role there. He was also one of the great product leaders at Google and at YouTube specifically. And most recently, he started a super successful, early stage investment venture capital firm called Home Brew. Hunter, thank you so much for being here. - Thanks so much for having me. - Hunter, you've had a really interesting career path. And I think you've struggled with something that a lot of us have struggled with. The question of whether or not management is right for you. So, going back in the past, you had become a really important product leader at Google, you're managing 40 people, which is huge on a product team. That's like managing in sales, probably 5,000 people. And you decided that managing people, being the boss, wasn't what gave you pleasure in your career. It wasn't what gave you strength. And you say it all started with a promotion itself. Can you tell us a little bit about your promotion to a leader? - Sure, you get promoted to management based upon the strength of your abilities as an individual contributor, not necessarily experience that you've had actually in a people manager role. And the help you get sometimes is inadequate or not as sophisticated as could help people, I think, move from a product manager of a successful team to a product leader who's actually managing those individuals. And so that was something that I had to figure out over time. And ultimately decided that it wasn't something I loved, that it was important that I enjoyed the chance to be in a place in the organization where my ideas, opinion, and input was important enough to help determine strategy. But that while I was happy to work in service of the product overall, managing 30 to 40 people wasn't what gave me energy. - Right. - After doing that for five years or so, that's what helped contribute to my decision to move from the operating side to the investing side where I could still very much care about people, care about founders, interact with them at a very human level, but in a different way, in a different relationship than you do in a sort of classic reporting tree. That's a pretty hard thing to realize. How did you decide what to do next? How did you decide even to think about that? - Yeah, it was really hard because I got stuck knowing that that was true about myself, but also not wanting to give up the position in the work and not wanting to be downstream from strategy. And I couldn't figure out how to separate the managerial responsibilities from the impact. And I just, I guess, recognized or realized that within some of these large companies, it's difficult to do that. And so that's where I sort of stepped away a little bit. I don't think I could have figured that out without taking a little bit of a sabbatical. I took sort of two months off in the summer of 2011 and was working through that question when my partner here at HomeBruzaccia left his job at Twitter. And so I sort of shifted my thinking from how am I gonna resolve this conflict of wanting to have impact, but not wanting to be a manager of a large team to, oh, what can such an I create together? - So it was really kind of perfect. I mean, the timing that you guys were both in this transitional phase. What would you guys have done if this hadn't happened so perfectly? - I think what I probably would have done would have been to take a year or so and step back a little bit, do maybe a variety of projects work on smaller teams, like leave Google and see if my kind of, let's call it my well replenished. Was it a situation? Was there something about the dynamic that was otherwise sort of convincing me that I wasn't happy or getting energy from managing or was it just a true statement about the sort of type of person I am where I was in my career? And I was gonna do that partially by talking to some folks who sort of self-described as loving being managers and see how much of what got them excited, what gave them energy resonated with me, as well as try to seek out people who'd been in my situation before, what did they do to resolve it? Did they just power through it? Or did they maybe decide that, you know what, they needed to be CEOs. For me, it was gonna be up the ladder or off the ladder and I picked off the ladder. - Yeah, it's really interesting, Hunter. As you know, I love managing teams, but the emotional labor that is involved in being a leader is can be exhausting. And when I decided to leave Google, I went from managing a team of 700 people to Apple where I was managing no one where I was an individual contributor again. And the irony there was in order to really think about how to operationalize management, I had to stop doing it for a good number of years because it takes so much energy, there wasn't energy leftover to operationalize what I was actually doing day to day. And also because when you've developed something that you know in your gut, getting it out of your gut and into your head and then onto paper requires you to take a giant step back. - Yeah, that's a really good point, Kim. Sometimes you just have to take a step back before you can see the larger picture. And Hunter, it seems like not being a manager there and going in a different direction was totally the right decision for you. Just a better fit, can't discount that at all. Really great story. - Hunter, thank you so much for being here. You are a walking living breathing example of radical candor and I'm really grateful to have you as part of our company and as a friend. - Thanks so much for having me on, Kim. - Thanks so much, loved hearing your story. (upbeat music) So I was talking to someone at Gallup recently about the different things we're doing, the candor coach and things like that. Many people I think might have heard of Gallup or at least read their name because Gallup had historically been associated with doing like exit polls around elections and things like that, but actually as a company, they've transitioned over the years and what they've become is more of a research-based performance management consulting company. So they're sitting on an awful lot of data about things happening in the workplace. And so in this conversation I was having with this guy at Gallup, he shared some really interesting data about management and I'll give you the rough kind of breakdown here, but basically he shared that somewhere in the neighborhood of 10% of people are pre-wired for management. You can actually often identify these kids on the playground. That person should be a manager. And I think as a parent, I've seen this before and of course I feel like I probably don't quite have that right, but through this conversation it became kind of clear that usually if you're having that instinct about someone, that might be one of the important markers that this person could potentially be a good manager. - What do you think, my daughter Margaret? - 100%, 100% Margaret will be a great manager. And then I'll sort of skip over the middle bucket and say there is some very large number of people, the numbers when the neighborhood of 50 to 70%, the population just shouldn't be a manager. There's no, there's really no case. And so it's this middle 30 to 40% that while not necessarily naturally predisposed, can absolutely be taught. I think this is really important. In the data, this data is directionally correct. I'm not quoting directly from the research study, but the really important takeaway is a really small number of people are ready to go out of the box to manage. A very large number of people should never do it. So I think what happens in a lot of companies, Hunter mentioned this in his interview where the top individual contributor ends up getting promoted to management. As I noted, I think that's pretty arbitrary, selection criteria. I think the problem is that how do you communicate to a team of people that someone other than the top performer is gonna get the highly coveted job as manager? Like, can you imagine telling a team, yeah, we're gonna take the lowest performer over there and we're gonna make them the manager of the team. - Well, probably not the lowest performer, but. Maybe if we had a less arbitrary selection criteria, it could be that the worst sales person on the team is the best candidate to manage the team. Yeah, you're right. Actually, I'm sold. So it's possible that even though you're great at your job, you shouldn't be managing the team. There's lots and lots of people who are in that situation. Yeah, and look, if you're not supposed to be a manager, if you shouldn't be a manager, if you don't want to be a manager, it doesn't mean you're a bad person. Just get in touch with what you really want and what you really care about like Hunter did. So you may be wondering about this. You're starting to doubt whether or not you should be a manager, whether it's the path that you want to take. Let's talk about some of the signs that you might not be destined for management, that you might hate being a boss. I think one of the tell tale signs out there is that you constantly find yourself gravitating toward or enjoying individual contributor stuff. And this one's a little bit, even maybe after you've become a manager, you still find yourself gravitating toward the individual contributor stuff. I think that if you're moving toward projects and individual contributor type responsibilities, you're almost necessarily abandoning your management responsibilities. And so if you find yourself moving away from traditional management responsibilities, which we'll get into in a moment, toward traditional individual contributor type stuff, that's a pretty important sign that maybe this isn't quite the right gig for you. Another sign that being a boss might not be the right role for you is if you cannot say truly in your heart, the people on this team, their success, is more important to me than my own success. And you've got to be really honest with yourself here. If you say this, do you really mean it? Be honest. You don't have to tell anybody what conclusion you reach. But you really, I just firmly believe to be a manager. You've got to put your people success ahead of your own. And I've seen enough managers out there who just don't operate that way. Again, not because they're bad people. It's just not really where they want to be. A lot of good people become bad bosses because they don't really want to be a boss. Yeah. And we're just trying to help you get in touch with that a little earlier. I recently had a meeting with a woman named Heather Kirkby at Intuit. And she had a great quote that I love. She's working in learning and development and helping get some of their manager programs, you know, redesigned, refurbished. She's really sharp. And she said, I want to restore the dignity to the office of management. I love this quote because, like, we've been in this game a long time. I've been operational manager for 23 years. And I have to be honest, I don't love this. Oh, there's a difference between leadership and management. Like, you know what? I'm with you. That is such BS. So it's, it's okay. Great. Let's have this wonderful intellectual discussion about that. I don't. Management matters a ton, right? You need to be able to have effective one on one. So you don't waste people's time and you get more leverage out of your team. You need to focus on the growth of development of your team. You need to prioritize how the team can best use its time. You need to learn how to say no, run staff meetings, give feedback. All of this stuff, you need to be good at to be an effective manager. And I love that Heather is taking this idea of I want to restore the dignity to the office of management. It matters. The stuff that managers do matters. And you've got to be excited about those things. You've got to be able to enjoy the one on one. So if you just view them as calendar clutter, you're not going to have good one on one. Absolutely. So think about those things that managers have to do and say to yourself, to those things seem exciting to me. That's how I'm going to be spend of my time, right? I'm going to be moving away from the individual contributor type projects and toward those other activities. Does that seem fulfilling? Richard Tedlow, who was a great mentor to me at Business School and also at Apple, used to ask a really good question. Do you want to be the boss or do you want to do the things that bosses do? If you don't want to do the things that bosses do, don't become a boss. That's an outstanding quote outstanding because a lot of people fall in love with the idea of being the boss. Yeah. For some. But they really want to do is they want to be King Kong and pound their chest. And that's not the reason to become a manager. Okay. That's exactly right. Hopefully asking yourself these questions and evaluating these ideas will help you progress your thinking about whether management is right for you. Look, being the boss is just not for everyone. So we want to encourage you to be open to the idea and not feel forced in a direction that doesn't make you happy and excited. Now it's time for this week's candor checklist. We've talked about how to ask yourself if management is right for you. Our tips today are going to be geared toward those who have made the decision. They've decided that management is just not for them. So if that's the case, if you've decided that management is not for you, here are our specific tips for what to do next. Tip number one, double check the decision. So even though we think it's really important to be honest with yourself and if you don't think management's right for you that you should not do it or stop doing it, it's still a really big career decision, right? And so find people you trust. Tell them why you decided this. Walk them through your thinking, your rationale. Look, I think a lot of people are going to tell you that you're crazy, but get them to tell you why they think you're crazy. At least who is behind the glass on our podcast, she leads marketing for us. She was telling me a story about this for one time. She mentioned to a mentor that she was doubting whether management was right for her. So, which by the way is already like really glad she's having this conversation and she's thinking about this and making it explicit. And the mentor said, look, you're way too early on to decide that. You'll close off a bunch of opportunities. For Elise at this stage of her career, this was actually I think pretty good advice. It made her realize she was actually still just in kind of the doubting phase, et cetera. But this is the kind of advice you're going to get and it might be good advice, it might be bad advice. And Elise's case was actually really good. But if people are counseling, you look, just be a manager because that's where all the opportunity is, you should start to raise that big giant red flag that you might not be, they might not be thinking about management in just the right way either. Tip number two, tell your boss if you don't want to be a manager anymore. If you are already leading a team and you've decided that you don't like being the manager, you don't like being the boss, you've got to go and tell your boss that you've made this decision. The reason is that your boss needs to help you manage this big transition. Even if it doesn't seem like that big of a deal to you, it is a big deal. It's a big deal to each and every one of the people who's working for you. It's a pain in the neck to get a new boss. And now you've put your boss in the position of making sure that your team remains happy throughout this transition. And along those lines, I would say at first especially only communicate with your boss. Because once you make this decision, if it sort of gets out, that'll cause a lot of churn, a lot of angst. So don't snatch defeat from the jaws of victory by having loose lips about this. Just go to the boss only and start to put in the right kind of transition plan to make sure your team has a good experience. Even while you're making a very high quality decision, you think they'll be better off without you. That transition is still very jarring to them. So please, please, please talk to your boss only to your boss and work through that transition in a high quality way. My husband Andy puts it very well. People can deal with change pretty well, but they cannot cope with uncertainty. And if you announce that you're leaving as the boss, but it's not clear who the new boss is going to be, you create a lot of uncertainty. Tip number three, be open and candid about your rationale for not wanting to pursue management. And just to be clear, this is after you've gone through the transition that we talked about in tip two, certainly make sure you don't create a lot of angst and uncertainty for the team by talking about this ahead of time with anyone but the boss. But after this is all rolled out, the transition happened and you're in your new job. Absolutely. Be open and candid about your rationale. Talk to people about why you made the decision that you made. Making this call is courageous and unusual. And I think it's a thing that more people should be doing. Again, I base this off of my experience. I base this off of some of the whack we get emails in about these bosses out there that are doing some crazy stuff. I mean, crazy. I can't even believe the stuff's happening out there. And a lot of those people would have done a lot of other people big favor if they would have decided earlier on not to manage people. And so most people instead, they tend to hang on. They just can't let go of this idea that the only way to advance or grow is management. And so you have an opportunity to be a positive role model here, right? And all you have to do is share your rationale with people and maybe help some other people avoid making a big career mistake as well. Tip number four, get clear on where your growth will come from. Just because you don't want to be a manager doesn't mean that you don't want to continue to grow in your company. A lot of companies don't have great growth opportunities for people who decide not to become managers. So it's really important to think about this. Some opportunities that you may take are to develop a really deep expertise or to broaden your expertise. So one path is let's imagine that you're a hardware engineer and you go really deep into audio engineering. Or if you're a hardware engineer, maybe you also want to try your hand at some software engineering. The first one being deepening, the second one being broadening. Exactly. You want to maybe look for some increase in scope. Maybe you can take on some new responsibilities that don't include management. - I mean, look, growth really comes from learning, right? Growth isn't inherent in one role or another, one job or another, growth comes from learning. And it's just important to get explicit about what direction are you gonna get your learning from. And of course, you should talk to your boss about your thinking on this. Now, one note here is be careful asking about this before deciding not to be a manager. And then, because you just realize you're at risk 'cause you might hedge a little, right? You might not see a path for growth ahead of you as a non-manager, and therefore you might say, you know what, I'm just gonna go on in and I'm gonna be a manager and it still might not be the right call for you. If you can't learn and grow where you are, you might need to find a new place. - If you start looking for a new job, if you go to a new company, talk to the hiring manager about how you'd like to grow in your career without becoming a manager and make sure it's a good fit for you. One of the things I really admired about both Google and Apple was the fact that both companies created a really clear career path, especially for engineers who didn't want to become managers. They could continue to grow in their career to have more impact to become better and better engineers, to keep learning, but they didn't have to become managers in order for all those good things to happen. And I think it was, it's part of the reason why both companies are so successful. - So to summarize, once you've decided, management is not for you. Tip number one, double check that decision. Tip number two, tell your boss that you don't wanna be the manager anymore and only your boss. Tip number three, be open and honest about your rationale for not wanting to pursue management and tip number four, get clear on where your growth will come from. You can revisit these tips and the show notes at radicalcander.com/podcast. We'd also love to hear about your journey through this process. So please feel free to reach out at [email protected] or by leaving us a voice message at 2626Cander. We'd love to feature your stories on the podcast or on our blog in the future. Believe us, others are going through similar situations and it can be so helpful to them to hear stories about people who are like them. - And that's it for this week's episode of a radicalcander. Our producers are Kristen Minter and Jennifer Leye. Thanks also to Laura Mayer and Andy Bowers at Panoply and to Elise Lockhart at Cander Inc. Our theme song is written in perform by Cliff Goldmacher. Please let us know what you think of the show and share your stories and questions with us. You'll find us on Twitter at Cander. Our email address is [email protected] and our website is radicalcander.com. - You can turn these ideas into action with the Cander Coach iOS app. You can get it for free in the app store. Also check out the radicalcander book, which is available as hardcover, ebook, audio book and the audio book is narrated by Kim herself. If you like the show, please help us spread the word and make sure to subscribe to us on iTunes Stitcher, your favorite podcast apps that you can automatically get each new episode. - Radicalcander is part of the onward project, which also includes side hustle school and happier with Gretchen Rubin. In a recent episode of side hustle school, we hear the story of an engineer who makes a thousand dollars on the side by snuggling. - Snuggles, that is definitely not my side hustle. There's no doubt about it. That's not mine. - I am a big snuggler. - Well, by the way, Kim, it turns out it's actually not that kind of snuggling. - Oh. - Yeah, so, curious? - Absolutely. - Yeah, well, you need to listen to side hustle school to find out what in the world this is all about. - I'm Kim Scott. - And I'm Russ Larroway. - We'll talk to you next time. - Thanks for listening.

Podcast Summary

Key Points:

  1. Hunter Walk, a former product leader at Google and YouTube, realized that managing large teams wasn’t fulfilling and shifted to venture investing, where he could still impact people in a more human, non-hierarchical way.
  2. Research suggests only about 10% of people are naturally predisposed to management, while 50–70% are not meant to be managers, emphasizing that many strong individual contributors should never take on leadership roles.
  3. Key signs that management isn’t the right path include a consistent pull toward individual contributor work and an inability to genuinely prioritize team success over personal success.

Summary:

In this episode of Radical Cander, hosts Kim Scott and Russ Larroway explore the difficult but crucial question of whether management is the right career path for someone. They share Hunter Walk’s personal journey—from a successful product leader at Google managing 40 people to transitioning into venture investing—highlighting that management wasn’t fulfilling for him despite his technical excellence. The discussion emphasizes that only a small percentage of people are naturally suited for management, with most strong individual contributors being better off in non-managerial roles.

Signs that management may not be right include a persistent preference for individual contributor work and a lack of genuine prioritization of team success over self-interest. The hosts present a candid checklist for those who have decided not to become managers: first, double-check the decision by discussing it with trusted mentors; second, tell your boss directly and only about the change to avoid team uncertainty; third, be open and honest about your rationale after the transition; and fourth, clarify your growth path—through deepening or broadening expertise—so you can continue to grow without management. The episode urges listeners to recognize that growth comes from learning, not just leadership, and to seek companies that offer clear career progression for non-managers.

The message is clear: being a boss is not for everyone, and it’s courageous—and valuable—to make an honest, self-reflective choice that aligns with personal values and energy.

FAQs

Look for signs like enjoying individual contributor work, finding your energy in team success over personal success, and being genuinely excited about managing people and having one-on-one conversations.

Yes — many people thrive in individual contributor roles, and strong performance doesn't always require management. Growth and impact can come from deep expertise or broader skill development.

Double-check your decision with trusted people, talk to your boss privately about stepping down, and be open about your rationale to set a positive example for others.

Absolutely — companies like Google and Apple offer clear paths for engineers and professionals to grow through deeper or broader expertise, without taking on leadership roles.

Ask yourself whether you'd sacrifice personal goals for team success. If you're honest and consistent in that belief, it's a strong indicator that management is right for you.

No — only share the decision with your direct boss to avoid creating uncertainty. Once the transition happens, you can openly discuss your rationale with the team in a positive, supportive way.

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