Do I Really Want to Be CEO?

I'm Muriel Wilkins, and this is Coaching Real Leaders, part of the HBR Podcast Network. I'm a longtime executive coach who works with highly successful leaders who've hit 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. Today's guest is someone we'll call Chloe to protect her confidentiality. She's worked across a number of different industries and geographies as she's pursued new professional opportunities and challenges.

And I thought, you know what, this is a great opportunity to go from HR director, which was kind of the level at which I was functioning, into that C-suite role and grow it. I ended up getting to help a couple of companies scale up to go from, say, the mom and pop. up to you know larger corporate structure so everything seemed to fall into place but chloe's most recent move wasn't quite what she had planned

She just became owner of the company that she had joined due to unforeseen circumstances that put the company at risk. She's since then been working to stabilize the organization.

But she's not sure whether this level of leadership is really for her. I guess here's the thing for me that I struggle with is I don't have any aspirations to be leader of the free world. I don't necessarily want to own a company, be the president, be the CEO. I work in public sector, and I was a fabulous cog in the wheel. You know, I performed really well. I fit together, worked well with the team.

I don't have any of that natural drive to want to be the boss. I'm finding as I do this role that I'm good at it in some respects. I guess part of it is I don't know... Do I want to really commit to this, to being C-suite, to changing from being focused on operations, tactics, logistics, and really take that next step into being a strategic leader?

I think I can do it. And now I need to figure out where do we go from here? Do I want to continue with this moving forward into being a true... C-suite executive and functioning at that level on a day-to-day basis or am I genuinely more happy in the operational side of things, letting someone else deal with the headaches of all this?

Over the course of her career, Chloe has found herself in the middle of new exciting challenges and always jumped right in. But now she's at a crossroads, questioning whether she wants to remain in a C-suite role. and if it's the right fit, personally and professionally. I think there's also an element of wondering if I can do it. I am...

I know I can learn things. I've always done well in school. I've always been able to achieve things. But I am a little bit scared about what if I fail. I now have... employees who are relying on this it's like the stakes are higher if i fail their health insurance goes away those sorts of things that i feel like

There's an ethical obligation that goes along with owning a company. It's not just about, can we make a lot of money? Can we go public? Can we, you know, these things, but people's lives are wrapped up in their work. And it's a different experience to feel that level of responsibility. I can barely show up at work with my pants on some days. I'm like, really, do I want to care for people in a way that this requires? And I think that's a serious obligation.

Understood. So it's a level of responsibility that makes you feel like the stakes are higher. For sure. As a C-suite leader. Yes. So there's a distinction for you between, do I want to do this? And can I do this? Yes. And what's the difference between the two for you? So the want to do it is probably.

my escape mechanism i can tell myself well i don't really want that and that way i don't have to figure out can i do it or can i not do it or do it well the can i do it i'm so opposed to the concept of imposter syndrome i feel like it's a false modesty but i also realize there's this real feeling that each of us carries that maybe i'm not good enough And here's the other thing. This isn't brain surgery. This is basically managing a business with...

four million in revenue a year. We're not a big player on the overall scorecard. So I feel like I'm just kind of stuck in my head too much about making everything a bigger deal than it needs to be. Yes, there are complexities with running any business, especially in certain states. Everything's going to be different. These are all manageable, and yet I work myself up into thinking, maybe I can't do this, or this isn't right for me.

So let me ask you a quick question. Well, I don't know if it's quick, but let's play a little game, all right? If you assume that you could do it, you had all the capabilities of being able to... do this role right and the role being operating at the c-suite level in this company that you now own would you want to do it yeah

That was pretty straightforward, wasn't it? It was. I didn't know it was going to be quick, but you did make it quick. And with confidence. Yes. Okay, you would want to do it. What would make you want to do it? What's behind you answering? that affirmatively and with what I sense is like an energetic confidence and honesty there. I firmly believe that a business can be run as a win-win scenario.

I believe that I can, as a quality business owner, I can provide an excellent service for a reasonable price and for those employees, I can provide a good job. that doesn't take over their world or their lives where they can have work-life balance i mean if i really believe that i could step up and do this well in my mind i can see an organization that people want to work for, and clients want to hire. That excites me.

It's like shopping at Nordstrom's where there's no risk because you know no matter what it is, even a bicycle tire, they'll take it back 20 years later. They want you to be satisfied. The other part of this is I don't believe that people... everybody should follow their dreams if everybody did follow their dreams where would we be as a country you know who wants to be a mechanical engineer maybe two people but if we focus on being

in a role where we can contribute and have a good quality of life to me that's a huge success so yeah maybe it's just insecurity that's keeping me from committing to this Well, let's see. Right. But what I hear right now is there is a want, a desire that is grounded in, dare I say, like like you find purpose in what the company does and how you can lead. Right.

And so that's a sense of motivation. You see a why, which is part of the formula. That's the purpose part of it. So we've established that. The question was.

If you knew that you could, you would, because you would want to. So now let's play part two to this game, which is if you knew you wanted to. Do you believe that you could, that you can do it? Yes. Not as confidently. Not as confidently. And what's going around in the back of my mind is... perhaps a tendency to procrastinate, or I actually wrote down what I think some of my weaknesses are. I added some strengths and some meh, but one of them was overcoming self-induced obstacles.

And I feel like I can often be my own worst enemy. So if I want to do something, unless I get some sort of fire burning in me that, you know, nothing can stand in my way. I sense that I will come up with some obstacles to self-sabotage or I know I need to develop my time management skills better rather than investing.

30 minutes and really dialing in and learning Airtable, I watch some dog rescue videos at the end of the day, you know, and I just go, hey, I worry that my own natural entropy will somehow. suck the life out of this and that's where then i get back to with this level of responsibility so years ago my husband and i owned

a business, and our whole lives were about being motivated, being focused, being present in the moment. And it was great. We didn't make money, but my God, we had the best friends. I don't feel that now like I used to. And so I worry that either it's because of age or life circumstances or whatever that maybe that drive isn't there underneath. And then I'll let people down as a result. Okay.

Understood. And so what is the level of drive that you think is required or the level of capacity, right? Because this is a can, not a want. What is the level of drive? that you believe is required to be able to do this role. It's reasonable. When you put it that way, I have... you know, a phenomenal employee who's helping me put systems in place, who's helping me make things more scalable. Yeah, no, it's a reasonable amount of effort to take on the portions that I'm responsible for.

Let's break this down a little bit because I think what's happening a little bit here. And by the way, I have no dog in this fight in terms of whether you do the role, whether you don't. Like, I want you to live your life. Live your best life, as the young people say. And what that looks like, I don't know. And it's totally up to you. OK, I just want us to sort of break it down a little bit so that you can make a decision based on.

the reality of things rather than what we may be imagining what this is. Okay. So you have presented this as a concern of not being able to do the role as you see it now. And let's just put that to the side for a minute. I'd like to understand in the role

What is it that you feel like you can do? So meaning, what is it that you actually bring to the table that are capabilities that you think support? this role and will help make it successful and be in service of the organization. Okay. So definitely being a jack of all trades is really beneficial here. Some unique experience with international work for our industry. That's incredibly helpful. Understanding how the different states function. I don't think there are a lot of people.

in my current role that have the kind of diverse background that i do a lot of times i often tell my partner you know we don't know what we don't know and the first thing will be getting a whiff of wow this is something

that I may not be familiar with, let me dig into it. And so having that kind of curiosity not to be arrogant and to be, you know, lest I make this about Ted Lasso, but... you know be curious and curiosity is really valuable in this industry and i think it tends to draw a lot of people who are incredibly confident maybe a bit arrogant so

maintaining that curiosity and identifying the things where there's even a little perception of weakness is a good opportunity to jump in and learn or ask for help. I'm not sure if I'm articulating that well. What do you feel like you're not articulating well? You asked me to list what are some of the things that I do well. I identify that I can identify when I don't know something. I mean...

So I find that really interesting because how could you leverage that skill that you have that you just articulated, which is one of the skills or what you feel like you bring the asset that you bring to the table. A capability is one of curiosity and the ability to. assess when you don't know something and then either dig deep and learn about it and learn it or ask for help, which is resourcefulness.

I'm curious now, how could you leverage these strengths that you say you have? Jack of all trades, expertise, operational, curiosity and resourcefulness. How could you leverage those? to close the gap or address when you might feel like there is a quote-unquote deficit in terms of the capabilities that you bring to the role. That's interesting because...

I'm very conscious of that, like being on the lookout for something that I might need help with or need to dig into further, but I haven't thought of how to apply it to my own role specifically. I feel a little bit stuck. Where are you stuck? I'm stuck in figuring out how to take the strength and apply it to where I am and how to do my job well.

So let's play it out, right? You just said you're really good at when you don't know when something is done or somebody else doesn't know how something is done, sort of seeking out the help. So let's name something that you feel you don't have the capacity or you can't. quote-unquote can't do in a c-suite level role right now okay so let's go with time management okay i do feel like overall my productivity

isn't where it needs to be because of my natural tendencies kind of going back to the operation side, well, I'll just work harder. And at some point I want to make the shift of how about we start trying to figure out ways to work smarter. work more smartly. So I'll at least use an adverb like a grown-up. But yeah, no, I think that time management would be a huge thing for me. Okay. And so is the issue there that...

you don't know how to do quote-unquote time management? I think I understand several concepts. I haven't played around with them yet to find out which one works best with my work style. And so... With different roles I've had in the past, I've basically just adapted whatever my boss used. And I haven't necessarily found one that just works well, resonates with me.

And that I'm able to maintain continually. Okay. As a result, I end up doing a lot of work in the evenings and on weekends. Right. And so what would it look like if we just use this as an example? What would it look like for you to apply, again, this strength that you have, which is, let me be curious about how it can be done and let me find some help in getting it done.

What would it look like for you to apply that in the area of time management that you've identified as an area of capability that you could strengthen? So I could set aside a block of time to look into systems or techniques or training tools for time management yeah i actually i delegated it to someone who does really well with time management and

That person has brought me something that's fabulous, but I haven't owned it yet. You know, I haven't personalized it. And as a result, I just spend a lot of time going, this isn't working for me. Okay. Trying to be all executive and delegate. Maybe that's something I shouldn't delegate, you know, because it is so personal. I mean, you can delegate up until a certain point, right? Right, right. You can delegate.

nine-tenths of the mile and still own the last one-tenth. Okay. I like that. I like that. Okay. And so it's not an all or nothing. Either I do it all myself or I ask somebody else to do it. I think it's what do you need to be able to cross that line? And I think what we're getting at is more around the areas that you have identified as potential gaps in capability for yourself.

in this role, are they ones that, one, you believe with the right resource that you would be able to close that gap enough, doesn't have to be perfect. Right. Enough. And then secondly, which we haven't gotten to yet, is do you want to? Yeah. Yeah. One hundred percent. I mean, I can. 100% to what? Which part? Yes to the first part. If I tackle things like my struggles with time management with a little bit of curiosity.

and maybe watch one less dog rescue video per day, chances are I would be able to come up with a system that works well for me so that I'm not spending time in the evenings and on the weekends.

playing catch-up the way i sometimes do now and if you were able to do that would you want to work on that yes so it you know it sounds to me like And correct me if I'm wrong, right? But it sounds like you want to do the C-suite role. I mean, you're in it, so you're doing it, right? You want to continue it, but it kind of needs to look a little different. in order for you to continue doing it. If it stays the same, then the desirability goes down. Yes.

And in order for you to want to continue to do it, you need to feel more capable in some of these areas where you think you're lacking. And again, I say feel. And so the question is. In reality, you know, you have a choice. You can either work on the areas where you feel you're lacking and see if you can do them, and then you have what you wanted, right?

Or say, you know what, which is OK. I don't really want to work on those things. And then you have your answer because you're not you're kind of not happy with the way it feels right now. So to me, it's more around how do you want to experience the CEO role and making a choice around it and then driving your actions based on that choice. It's pretty genius.

You tell me how you make sense of what I just said. I think you nailed it with the way I'm experiencing it now is not something I necessarily want to continue in perpetuity. Where I am now just doesn't have a very positive feeling on a day-to-day basis. It fluctuates. On any given Tuesday, I'll have wild confidence and just feel like we're nailing it.

Daily, I'm just not feeling like this is where I want to spend the rest of my career. However, one of those things that I do well, that curiosity, if I apply it strategically,

it can change the entire perception of what I'm experiencing on a day-to-day basis. And so I'm willing to do that when it comes to... researching a legal concept or a hiring practice, but I've just never thought of turning it inward a little bit and being curious about some of my own professional practices and processes that I've developed over the years. Some with phenomenal mentoring and some just by seat of my pants.

let's pause before we get into more specifics of what Chloe is really trying to solve for. Sometimes in our career, we start with a very specific goal and make choices along the way to get us there. But other times, we just accept the opportunities that come our way. That puts us in a different position, from one of thinking, I know what I want, how do I make the right chess moves to get there, to...

Is this really the right opportunity for me? An important distinction to make is between do I want this role and do I think I can do this role well? Chloe didn't hesitate when it came to answering the question around whether she wants the role. So now we can really zero in on what it would take to make her feel like she could actually do the role. And to do that... I turned to her strengths. What would it look like if you were the chief administrative officer of Chloe?

What would you do? What would you chiefly administrate differently? What would you chiefly administer differently in how Chloe does? That's a great question. I would most definitely start with building some structure and some processes around, well, a lot of it comes to defining. Sorry, I'm backtracking here, but that goal setting that I just naturally do for certain aspects of my life, I've got this blank here where I haven't done any of that. So establishing what are some of my expectations.

for whoever fills the role of CAO for this particular company, and in structuring my daily processes so that I can achieve each of those goals. I really love being... incredibly good at my job and I think that part of the element here is that I'm learning in real time and so I don't come out at the end of every day and go I killed it I rocked it I'm so amazing

That's okay because that's how we get better, you know. Those windows of time where I was in a role that I had completely become proficient in, they might feel good, but it doesn't. progress further. So I like the idea of looking at the CAO role and identifying what does it take for this role to be successful and what do I need to adapt in my daily administration of this role. to make it look like how i want it to be yeah because you have ownership and control over that i do wow

Right? Right. Oh, my gosh. I think it's fascinating that you do that for everything else. Oh, that's good stuff. And it's sort of applying it for yourself. Right. And I think there's a little bit of like, you know, look, I get the. hey, I don't walk out of here every day feeling like I rocked it, you know, and I like nailed it. I mean, welcome to my life. Okay. And in those moments, I would say, yes, establish what success looks like.

But then give yourself a progression path to get there. So the celebration, right, and the victories don't only need to come. When you've hit the final success criteria. Right. One of the things that I love in my little fitness circle is, you know, when people say they say, oh, I have an NSV.

to share and it's called a non-scale victory where the victory is not based on the final number that you were achieving on the scale right it's guess what i was able to do 10 push-ups today right love it and that it's part of the path OK, and it might feel small relative to the bigger goal, the Uber goal, but it's still a victory. And so what I would suggest is, as you define.

what success looks like for this role, regardless of who were to sit in it, to also not lose sight of defining what these... non-scale victories are along the way, the mini victories, right? And sometimes it might just be, I made it through the day with only looking at five dog videos instead of 10. Yes, yes. I love that. I love that. Yes. Non-scale victories. I think that's the word. I don't know. If not, I just made it up. It's a good one, though. It's a very good one. Okay.

And so if you can use, which is what you've just identified, if you can use what you actually bring to the table, the things that you can do to address the areas that you believe right now you can't do. I'm curious what happens, and I don't know. I think that's TBD. Right. It's untested. Very untested. We can't really right now say with assertion that you cannot do those things. True. So the question now is, do you want to test it out?

Do you want to give it a chance to see if you want to prove to yourself or prove that you can do it so that you can make a better informed decision down the line? Or again, is it like. I don't even really want to know if I want to test them out, which is okay too. Right. No, 100%. I want to test this out.

I feel like you've just identified there was an incongruity somewhere that, you know, like I have this skill set and I have this problem and I kept going at them like this. And now we've just somehow managed to. say, at least take your existing skill set and apply it to your existing problem and see what happens. What a novel concept. So no, I'm very curious now to see what impact this has on my day-to-day experience of this role.

And hopefully the continuation of that is then it has a positive impact on the company itself.

I want to go back to something that you said earlier, which is this concern about when you were talking about, can I do it? You said, you know, what if I fail? You know, what if I fail? And there's something about that for me, which is like, it seems like you have clear in your mind what failure could look like, but you haven't quite articulated what success could look like. That's a great point.

It's hard to determine if you can be successful if you haven't really determined what success looks like. Very much so. So this point that you brought up, which is around, I need to sort of sit and think about, regardless of who were to sit in this role.

How would we define success? What would it look like? Right. Okay. No, I like that. I like that. There's a question that's been on my mind and I didn't ask it earlier on because then some other interesting things came up, but I'm curious when you. became an owner because obviously you did not have to become an owner just because somebody makes you an offer it doesn't mean you have to pick it up and especially to buy a company you don't you're just like sure why not yes why not

Right. What made you become an owner? So if my current partner and I had not bought the company, it would have closed. It would have gone under. the people then who were employees and the clients we were serving would have been left in the lurch. I felt like we were the one and only hope for it to have a chance to make it. We both realized we may fail with this going into it, but we didn't see anybody else around us interested or willing to step in, pick it up, and run with it.

I saw an interview with Bob Geldof where he was saying that one day, you know, God knocked on the door and this scruffy Irishman answered. And God was like, ah, you'll do. But it was that thing of not even necessarily being. the right person for the job but being the only person available at that moment to step in and do it. And I think my partner and I both have very strong senses of responsibility.

Whether it's a nurturing or, you know, just wanting to make sure everybody's okay. Yeah, we just, we felt like we could do it maybe, so we had to try.

You've used that word. First of all, thank you for sharing. I love the fact that I know who Bob Geldof is. Thank you. That's awesome. Makes me happy. Certain age. Yes. Yes. And. You've used the word responsibility quite a bit, and it sounds like it is a deeply held value of yours, right? As you say, just answering the call when called, opening the door. Even if the reaction to the people who knock is, you'll do. But guess what? You're the one there. Okay. And yet that was your motivation to.

own this company to pick up the mantle and and take this responsibility so it was a motivation it moved you to action it moved you to buy this company and step into the role right that's what motivation is it moves you to action And yet, fast forward to today, the way you articulated responsibility now when you said you're concerned about failing and you're responsible for all these people and their livelihood, it is... in a way keeping you from moving forward as well so on the one hand

You are at times experiencing responsibility as a motivation to move forward and move to action and be resourceful and do all the things that you need to do to keep this company running. And on the other hand. I'm almost imagining that this responsibility is weighing you down to the point of not moving forward, right? It's a burden. Right. Okay. So same coin, two different sides of how you experience it.

Interesting. Well, before I move on, tell me what's interesting about that for you. I like the idea that it can be this one concept or entity responsibility and yet it can have a different... impact on me depending on how I'm looking at it or perceiving it or yeah I'd never thought of it as like two sides of the same coin right

And so my question is, what if it's not either or? What if you did this role holding on to this deeply held value that you have, accepting that leading in a responsible way? is holding the whole coin, meaning it is both motivational and at times heavy. I like that. And I like the idea that... Something that I keep in my back pocket, this curiosity, is something that can help me with both the burden and the motivation of responsibility.

Yeah, because, you know, look, I'd be foolish to sit here and tell you, oh, my gosh, Chloe, it's never a burden. It's never heavy. It's never. No, like, let's be real. Right. You know, it's like. You know, I'm not a religious person, but I know enough because of my mama. You know, but there's the verse, right? I think it's a verse. To whom much is given, much is required. Yes.

Well, that's awesome and inspirational and motivational. And, oh boy, what do you mean too much? What do you mean much? Like how much? How much requirement? The reality of it is the more we resist that there is also a much and a required, the heavier it becomes. And so my question for you is in practical terms. How do you carry this responsibility, which is real? Again, I don't play fantasy fairytale land. How do you carry this responsibility in a lighter way as you lead?

moving forward, what could you do? I think facing it, articulating it, writing it out, much like my... ongoing list by my bedside you know when things keep me awake at night i write them down so that i don't forget them and it allows me to move on instead of letting responsibility be this nebulous monster that lives in my head I can quantify it and make it into the many pieces that I can tackle it in a more believable way with curiosity, with help from my colleagues, with all the different.

tools at my disposal yeah so again instead of letting it be something that just gives me kind of an icky feeling on the inside it would be really nice to treat it like any other business problem

Yeah. I mean, what I sense, Chloe, is like, if I had to name just from the brief moment that I've known you, but like, I feel like one of your superpowers. And you tell me if this feels off to you, right? Sometimes I'm like, oh, this is a superpower. People are like, no, that's not it. And that's fine, right? I want you to be able to say, yes, that is, is resourcefulness. And here's why, right? You've moved all over the place.

You've had this like career that is so diverse, like you've made pivots that most people wouldn't even imagine that they could. Right. But somehow there was something that said, yep, I could start off as this. And yeah, I can do that, which is completely different than what I was trained for. Oh, the company's up for sale and you're offering me a bite. Yep, we can do that.

Right. We'll do it or we'll figure it out. It's not even we can do it. Actually, it's the we'll figure it out. There's a difference. There's a difference between saying I can do something and. I can figure out how to do something. And if you leaned more on the I can figure it out versus I can do it, what difference do you think that would make for you in terms of being able to carry this responsibility?

I love that distinction. And that is 100% how I see the world is, can I figure out how to do something? And if so, then it's a risk worth taking. like to think that i'm not necessarily risk averse but i'm risk aware and i think just by being aware of things i can then wrap my head around yeah we can figure this out yeah no that's it's a great

Great insight. Yeah. And let me tell you something. If there's one of the big capabilities that a C-suite leader needs to have, it's being risk-aware. Right? That is one of the main jobs. Right. Right. So. OK. So tell me where you are now, because I feel like we've covered a lot of different pieces and you have.

come to some answers, I think, on your own. So I'd love to know where you are now relative to where you were when we first started the conversation. I feel great. You nailed it. Oh, no, you nailed it. You nailed it. This is incredible. You've helped me get to a point where I can identify what the sort of the vague sense of dis-ease or discomfort.

that I've had around my role and what I'm doing professionally right now and look at resources and tools that I have at my disposal, that if I just turn them and focus them, they can perform for me in the way they do for me in all of my business dealings. So I find it very interesting that I could have such a huge blind spot internally.

about what's going on and yet just having a conversation with you and having you ask some pretty pointed questions has helped me realize you know that there's a not an easy solution but a feasible solution Mm hmm. Yes. Yeah. And I love that distinction because, yeah, it's not always easy. And what we're looking for is, is it feasible? Right. Right. And so I don't know.

what the answer is going to be, right? Around, do you want to continue doing this? I think you need to test some of this out a little bit. Agreed. And that's your homework. Okay. Test it out. Be your own chief administrative officer to yourself and see what happens because I don't think you've done that yet. I have not. Okay. Not even a little bit. This is super helpful.

Taking on any new level of leadership, but especially the head role of an organization, means stretching ourselves in a number of new ways. So it's important to underscore a nuance that makes all the difference. You don't always have to know how to do something. What's more critical is knowing you will figure out how to do it, especially when we grow and move into uncharted territory.

That's it for this episode and for Season 10 of Coaching Real Leaders. We'll be back in 2026 with more new episodes and some new surprises. Until then, there are plenty of ways for us to stay connected. If you haven't already, check out my new book, Leadership Unblock, where I explain the seven most common blockers leaders face, many of which are issues that surface on this show.

I'll also be holding a 10-week Leadership Unblocked group coaching intensive starting in January, 2026. This is the first time I'm opening this to the public, and I'd love for you to join me. You can find out more and register at leadershipunblocked.com slash group. To not miss when the next season starts, make sure to subscribe, rate, and review the show. It really does help.

And if you're facing a leadership challenge you'd like to work through with me, consider applying to be on the show at coachingrealleaders.com. And of course, you can always find me on LinkedIn at Muriel Wilkins and on Instagram at Coach Muriel Wilkins. or become a member of my community at coachingrealleaderscommunity.com, where I host live episode debriefs and Q&As.

Thanks to my producer, Mary Du, sound editor, Nick Kringko, music composer, Brian Campbell, my chief of staff, Emily Sofa, and the entire team at HBR. Much gratitude to the leaders who join me in these coaching conversations and to you, our listeners, who share in their journeys. From the HBR Podcast Network, I'm Uriel Wilkins. Until next time, be well.