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Fit Happens asks the question most leadership conversations avoid: why do talented people fail in the wrong roles — and thrive in the right ones? Hosted by Jason Baumgarten, an executive search specialist with decades of experience placing CEOs and building boards, each episode blends cutting-edge research with candid conversations with the leaders who've lived it. Because fit isn't luck. It's a science.
Jason Baumgarten 00:00
I'm Jason Baumgarten and you're listening to Fit Happens, the podcast where top leaders, investors and board directors share the stories, surprises and hard earned lessons behind finding the right fit. Let's Get Into It. Here's a question I ask CEOs, and not that many of them can answer it. If your time is your most valuable asset, and I don't think we can debate this, who's actually deciding how yours gets used? Because for many of the leaders I work with, the honest answer is it's not really them.
I'm Jason Baumgarten and you're listening to Fit Happens, the podcast where top leaders, investors and board directors share the stories, surprises and hard earned lessons behind finding the right fit. Let's Get Into it.
We recently talked about the fact you have roughly 4,000 weeks, not to make you anxious, but to make you honest. Because once you translate life into weeks instead of decades, it gets hard to pretend that there'll be a later moment when you finally get to the things that matter.
I want to take that a step further, because once you accept this premise that you've got finite time, a slightly uncomfortable question tends to follow. If time is your most valuable asset, who's deciding how yours gets used right now? Interestingly, when we're early in our career, we generally think that somebody else tells us what to do, how we should be spending our time. In fact, we might even be clocking in and out. But presumably as you get more senior, you get to dictate how you spend your time, what you think's most important. But if time is your most valuable asset, who's deciding how yours gets used? And when I started looking at the leaders I work with, senior executives, CEOs, people with enormous responsibility on paper, I see this funny paradox emerging. They have authority over strategy and budgets and headcount and people, but often very little authority over their own time. Or at least they're not taking the agency to have that authority. Their weeks are shaped by expectations that they didn't set, and meetings tend to just add up over the years. There's cultural norms that nobody really sits down and says, we're going to now have a meeting. And you, you've had it for years and it just falls on your calendar. And these things start to become inevitable simply because they're arriving. And slowly your calendar becomes almost like a fate.
So I want to talk about fit through a different lens. Not alignment, not chemistry, not performance. But you know, fit is authority over your time, because, you know, misfit in a role doesn't tend to announce itself as some dramatic failure. It's this creeping succession, this drift, and that often shows up as a calendar that you didn't design.
So I want to talk about this concept of default versus designed time. So over the years, leaders have told me the same thing, or versions of the same thing. Hey, I like my job, I respect the people and I get paid well. And the vision, the mandate all makes sense. But, you know, I feel really busy and I'm not sure the work I'm doing all matters equally or where it came from. And so then I say, well, let's not be philosophical about it, but let's get practical. What did you do last Thursday, or last week, or last two weeks? In fact, many of them I've said, take the last two weeks, or just two weeks at random, and map out where your time went.
And what emerges is that it's usually not some big fancy workload problem. It's not something AI needs to solve. It's simply a control problem, that the weeks, at least the ones that many of them pick and map out, are dominated by the urgency of others, other people's priorities, other people's anxieties, other people's preferences. And these leaders are responding more than they're choosing. They're letting all these other urgencies dictate how they spend their time.
Now, as a leader, part of your job is to be reactive to the people around you and to help them manage their anxieties and to help ensure they're focused on the things you want them to focus on. But the problem is that over time, that really takes a hold of your life and your calendar.
Now, quick sidetrack. I worked with a CEO recently who's super capable, very respected, and was hired with a clear mandate. That job was to transform the business. And on paper, it was a great match. Experience fit the values, everything aligned. The board was supportive. And I was catching up with him, I don't know, about eight months into the job, and he was just exhausted. He wasn't totally burnt out, but he was just depleted. I could tell, having known him for decades. And I didn't ask him about the strategy or the performance, how the business was doing. I just said, take me through a week, let's pick a week two months ago and let's just walk through it. Not an ideal week, not a board meeting week, just a week. And after we started going through it, about 10 minutes in, he realized that all of his time was being dictated by other people. Internal alignment, check ins, pre-meetings, meetings, political choreography. And he wasn't really doing what he was hired to do. Even though things were going well, he realized that he was getting sucked up in the moment of buffering the organization from this transformation, some of which was absolutely required. But how it was getting done was being defaulted by others. Whether it was his EA, his chief of staff, his senior cabinet, his senior executive team, they were all sort of getting him to respond.
And so I said, have you ever thought about the idea of designed time, designed weeks versus default weeks? You know, how do you sit down and say, hey, we've got all these meetings, let's actually audit them and take a bunch off the books? How do we start to have a culture of taking things off as opposed to adding things on? And this designed week concept anchors around a point of view that your conscious trade offs are, these are the things that deserve my time, these are the things that do not, and that fit, that concept that we talk about on every show, is the difference between the two. And the misfit is often not a values clash or performance issue. It's just this agency loss over time.
So let's talk about where this goes wrong, because it happens everywhere. The first is what we just talked about, the borrowed urgency. Your time, your calendar is dominated by things that feel important because someone else really cares about them. And it could be someone really powerful, a board member, an investor, one of your top executives. And the problem is, it may not actually be important to the work you are hired to do or that you want to get done. It may just be important to them. And that can feel urgent and consequential. And you're a super conscientious person, so of course you want to respond and be helpful. But borrowed agency crowds out your own priorities. And it might be that you feel tired, not because the work was hard or these meetings were hard, but simply because they weren't your agenda items. It wasn't your thing that you wanted to get done or that you were hired to get done. So the first thing is look at, are you getting sucked into the borrowed urgency trap?
The second is something that I've talked about a lot over the years. It's drift. And this is often when something you are doing has sort of drifted into something else. And this can be a team that isn't performing well, and you start first by trying to figure out what's going wrong. And then you start actually doing the work. And then you start attending more meetings and more work sessions and you suddenly have a different job description. You're compensating for a gap somewhere else in the organization, you become super glue. But it's not a long term fix. And these things happen. It can happen where you're doing somebody else's job, it can be you're somebody's counselor. And just because you're good at it, it doesn't mean you should keep doing it. So go back to what was I hired to do, what's most critical, what's on my agenda, and make sure that's what you're spending your time on, and that you haven't drifted into helping the organization in some other way that might be important, but you probably aren't what should be solving for. So just because you're good at it, just because it needs doing, doesn't mean it deserves all your time. Particularly after a first period of diagnosis.
The third thing I want to talk about is an emotional handcuff. You know, we all talk about the golden handcuffs. You know, compensation becomes the justification for tolerating a bad use of time. You know, they pay me too well. But I actually want to talk about the psychological handcuff, because I think that often there are things that suck us in because it's a prestigious committee and we all want to be a part of it. So we start sitting on the committee because we don't want to be left out. We don't want FOMO. So we're joining this committee week after week and we sit around going, I don't actually need to be here. And so think about those things that are psychological handcuffs. It could be compensation, it could be fear, it could be prestige, it could be simply, you want the optionality because maybe something will happen and you want to be there. But really being mindful of, am I here because I need to be to advance my mission, or am I here because of some other psychological reason that I'm not being honest with myself about?
And when you go through those traps, when you think about other people's urgency, role drift, and psychological handcuff, you often realize that you're just getting a lot of your time sucked away.
Now, I want to challenge a common idea. And for senior leaders, we've all ended up talking about work life balance a lot. And one of the issues is it's not often really a balance question, it's a power decision, because who has the power to decide what deserves your attention? And by attention, ultimately I mean time. Who has the power to say no and you stick to it. Who has the power to protect your thinking time, the depth of your thinking? Because a lot of senior leaders have positional power, but very little temporal power. And your title suggests autonomy. But your calendar that week I asked you to pull up tells a very different story.
So how do you get some time back? And one of the things to look at is the systems you're using. I often love the idea of not just a commitment or a decision or a recognition or a diagnosis, but what's the ongoing system? Because you can often fix the week ahead, two weeks ahead, with a one off audit or a meeting with your team. But then you have to look at what is the system going on. So who has access to your calendar? How do you actually proactively schedule your time? What decision frameworks are you using? What decision frameworks are other people using?
So a simple time authority test. Pull up your calendar and ask yourself three questions. What can I cancel without asking anyone's permission, that I should? What might I actually need permission or coordination or collaboration to change, whether we have this discussion, meeting, check in at all? And what can I not touch at all? And be honest with yourself, because you might find that actually you can do all of it all on your own, or there might be some things that your board's asked for or some person that's really critical that you need to keep, even if they really don't have power over your time. You really can't change that meeting without a conversation. But just be honest. And if most of your time is on things that you can't change, then you have to step back and say, what is the system that's allowing that? Is that appropriate for what you have to get done? Or have you gotten sucked into a difficult state?
And the goal is, you've got finite weeks, and so what can you control? And if the answer is a lot, then you've got to take back the control. If the answer is I can't, I actually don't have control, then it's not about rebellion, it's not about being difficult, but it's about having clarity. Sit down with those people who have power over your time and say, hey, I've got to get this done, how does this meeting, this schedule fit in? And you have to have real trade offs, because not only will that drive what you're able to accomplish, but it's going to help you with your fit, it's going to help you with your happiness, it's going to help you with your energy. And that is a trade off over time.
So last time we talked about this, I asked you to do kind of a more-or-less exercise, to look at actual weeks, what made you feel larger, what made you feel smaller. And this is really the next step. Know what deserves more or less, and then extend it to, do you have authority, not just conceptually, but practically, to act on that knowledge. And if you don't, it's not some moral failing or philosophical failure, it's just structural. And it simply means the work isn't going to self optimize to make it better for you. You need to renegotiate the expectations, the scope, what you're here to do, what your role is. And what's really amazing is that just by having the conversation, often you'll find people change how they ask you for your time.
I worked with a CEO years ago who had a rule that if you were in a meeting and you realized you didn't need to be in the meeting, you had an obligation to get up and leave. Now, in most companies, that would be an insane thing to do. In this company, it was very common, people would just, five minutes in, get up and leave or drop off the Zoom. So, you know, maybe a little rebellion, if you really don't need to be somewhere and it's not culturally going to make you a pariah, just disappear and see if anyone notices. Now, if you are a leader, people will notice, in a bad way, because if you leave, you've cast judgment on the meeting. So maybe you need to do it a little ahead of time, or pause the meeting and say, hey, I realized I don't need to be here because you guys have this under control. Is there anyone else who feels like that, and we should leave them to it? And see if that's maybe a powerful thing, to give other people some permission to take back their time as well. Because it's a fit conversation. And when leaders, and when we all reclaim authority over your time and your weeks, your performance will absolutely improve. Not because you have to work more, but you start working on the right things, and you're being busy on the things that matter and that you've prioritized.
So I leave you with this. Your weeks are being spent, and you're going to work, and you're doing those things, and they're being converted into energy, whether you're really conscious of it or not. And the question for you is, are they being spent for your biggest purpose, for your biggest what? And then the most powerful thing is when you get a hold of this at work, then get a hold of it at home and start to think about the even more precious time that you have at home, you know, with your family. Where are you spending that time? Because what I find is that the same exercise, it's a little bit harder to do, because it tends to not be as scheduled. So you have to rely on a little more work to figure out where your time is going. But if you realize that you're racing home to spend time with your kids and you spend half the time unloading the dishwasher and checking the mail and fixing something around the house, you're not actually prioritizing your time the way you intend. So if you get a hold of this at work, then turn the system inward to your life beyond work. What parts of leadership still deserve you, and how do you make those choices before they get made for you, at work, at home, in your community?
I'm Jason Baumgarten, and this is Fit Happens. Thank you for spending a few minutes of your finite time with me.