The Ryan Hanley Show - Never Chase a Title (and what you should chase) | Kelly O. Kay

Episode Date: October 13, 2026

A CEO search for a big-brand public company. A name comes up, and the chairman of the nominating and governance committee shuts it down. He knew that person 20 years ago, and that person was a jerk. A reputation from two decades back, settled in one sentence, in a room the candidate never saw.Kelly O. Kay, a partner at Heidrick & Struggles and co-author of Show Up to Win, was working that search. He tells his six kids never to chase money, and he tells executives never to chase a title. Chase the CEO title and you'll get it, at a company you won't want to run.I break down more field-tested decisions about trust, selling, and growth inside C.R.E.A.M. One useful experiment, playbook, teardown, or take each week. With receipts: https://ryanhanley.com/subscribeWe get into why saying yes to a conversation while you're happy isn't disloyal, and why competitive leaders win the process and then can't say whether they want the job. I tell Kelly about the job I took for the title and the money, and hated. His answer: they question your judgment, so call out what you missed. Do that, and a short stint stops being a hole in the résumé. His advice for a role you've never held sounds like weakness and reads as strength: ask for a coach as part of the negotiation.If this made you question whether your next move is built around your edge or around a title, get on the Easy Mode waiting list for book resources and updates: https://ryanhanley.com/easy-modeConnect with Kelly O. Kay: Heidrick & Struggles: https://www.heidrick.com/en/people/k/kellyokay LinkedIn: https://www.linkedin.com/in/kokay Show Up to Win: https://www.heidrick.com/en/pages/show-up-to-win-bookWatch Finding Peak on YouTube: https://youtube.com/ryanmhanleyFollow Ryan: Website: https://ryanhanley.com Instagram: https://instagram.com/ryan_hanley X: https://x.com/rhanleyThis is the way.Hanley. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

If you give them reason to say things that are negative, they're going to, A, they're going to say it, and B, they're never going to forget it. I just had a recent situation where Jeff and I are working on a big branded public company CEO search on the non-gov committee chairman, heard a name that came up and said, nope, wouldn't want to engage that person. I knew that person 20 years ago, and that person was a jerk. Kelly, it's such a pleasure to have you on the show. Thanks for taking the time. Ryan, it's great to be here. Thanks for the invite. Why do so many executives move positions so often today versus kind of what we traditionally

believe to be true, say in previous generations where it was like you get in, you work your way up a company, you get to an executive spot, and that's kind of like your career. That's like what you do is like you're the VP of this company for 25 years and you know the company inside now. That just doesn't feel like the culture today. Why did that happen? What was the change? Yeah. Well, there's just so many companies, right? There's so much capital. There's so much capital creating so many companies. There's so much innovation. There's so much new technology. There's just an abundance of opportunities and options today that didn't exist 20 years ago, to your exact point. And the money is just incredible, as you know, and your listeners know. So there's not

new and exciting technology, which means typically growth and most people want to be in a growth environment because it's fun versus a environment where it's a big, heavy transformation or big change from one business model maybe to another. So there's a lot of reasons for it, but I would, in my opinion, it really comes back to capital innovation, just the amount of options that have been created that didn't exist however many years ago. Do you think there's a lot of pressure to chase that growth? Because over my career, I've met a lot of people who are brilliant in whatever regard and good at what they do. And, you know, they hop around and they're at different companies

and, you know, every two or three years, they're doing something slightly different or in a different place. And I see nothing wrong with that. But you meet. some of those people, and it doesn't seem like it makes them more happy as they move from job to job. It almost seems like they would be happier setting down roots, becoming that subject matter expert, or knowing that division inside and out. Yet there's this like, it almost feels like there's this unspoken pressure that you're not growing if you're staying in one position too long. Do you think that's a real pressure that people are feeling? Yeah, I think, listen, I think, assuming we're talking about people that voluntarily leave versus involuntarily leave.

Yes, yeah, yeah, voluntary, yep. So that's what we're talking about. Listen, I think there's a bunch of, there's a percentage of the population that are chasing money, chasing titles, chasing whatever. And the reality is, and we talk about, and by the way, thank you for reading the book. I appreciate it. Jeff, my co-author appreciates it. What we talk about is stay in a role long enough to have achieved something.

The people that move around constantly, the way that is assessed and viewed by boards and CEOs and C-suite leaders is there's really no loyalty. You haven't really shown you can stay long enough to have any real impact in a company. And if that's all you're doing is chasing money, and we talk about it in the book, I have six kids and five of them are in the work world. And every one of them, the advice is never chase money. If you're good at what you do and you know this and your audience knows this, if you're good at what you do, money will find you.

Like that is the worst thing you can do. But yet a lot of people still do it. They also chase titles. They chase CEO titles. They chase whatever title. And the reality is not everyone is meant to be a CEO or a C-suite leader. And that's okay. Just be the best you can be at whatever your passion is.

How do you know what title you're meant for? Because I think that I will say earlier in my career, I certainly wanted, you know, I have an ego like anybody else. I have ambition like anyone else. I wanted to see CEO, you know, after my name. Like I wanted to see that. You know, I think, and maybe this is a secondary question that answer as you will. Like one, so how do you know which title is.

best for your, which layer is best for you in your career? And then out of that, like, do you believe that there are seasons for those titles as well? Because that's kind of where I've fallen. Like, there are seasons to be a CEO. There are seasons to be a different position. And how do you manage all that? Yeah. My advice to leaders, to my kids, to everybody is never chase a title. Like, chasing a title, like one of your listeners, could say, I want to be a CEO, and guess what? You will be a CEO, but it's of a company that you're not going to want to be a CEO of. I mean, that's, it's, so yes, you got your title, but now you're in a, if you don't really have the background and the skills to get into the high quality company, you're going to spend two or three years of your life, and it may not amount to much. That's kind of the probability. So what my advice is always been, and we talk about it in the book, we lay out frameworks to do this, which is, Look for the highest quality company, the highest quality role. That's what really is the best path for building a career, in my opinion.

And I think we talk about it in the book a bunch, assess companies on quality rather than just the title. I mean, the amount of people that over my 20 years and Jeff's 30 years that will say, I want to be a CEO, and you look at them in the eye and their eyes shift up into the right or they look down or they, I can tell instantly they're saying it because their spouse thinks they should say that. They think they should say that because Jeff and I are recruiters. They say that because their social network thinks that they should be a CEO. But the reality is, unless you're looking someone straight in the eye and saying, I want to be a CEO.

And it's not a time frame of being one. It's about building all the skills. So the time that you do get in there into that seat, you're prepared for it. I also think that people don't take enough time to think about the lifestyle that comes with the position, right? Like, if you're a CEO and something's on fire in your company, it doesn't matter if you're at a little league game or dinner with your spouse. Like, you got to put that fire out. Like, the buck stops with you. And, like, I've had people in my own life who chased the title, wanted the spot, got to the spot,

And then you ask them how they're doing and they're like, oh, you know, I'm okay. And I'm like, it's like, dude, this is like what you wanted. What do you mean you're okay? Like I thought. And it's, there's so much peer pressure and even, not even peer pressure, like social, almost like self-inflicted social pressure that you put on yourself without any regard for what is the actual lifestyle that I want? How do you, when you're working with someone in a placement perspective or trying to find it, like, How do you talk to them about managing or thinking about lifestyle to the position that they'd actually be taking and how that mashes up? Yeah, one of the things Jeff and I talk a lot about, both behind the scenes and when we were writing a book, which is over many, many years, leaders like yourself and your listeners, they're very competitive.

They get into a process and then something happens where they want to win. It becomes a competition, almost irregardless of what their interest is. They want that job and they want to win it relative to everybody else that's competing for it. And so very often you get to the end of a process and you say, Ryan, congratulations. They're going to make an offer to you as a CEO. Do you really want the job? And you're like, I don't know. It happens all the time.

But the reality of that job, of the CEO job, which is unique. is it so lonely? You just talked about it. It's lonely, not only just for the reason that there's a problem, you're at your little league game, but you have the board dynamic. You have the investor dynamic. You have the employee dynamic.

You have your own family, your own health. You have the strategy. You have the payroll of everybody in your company. You literally, and who do you talk to? You can't go talk to your board about the most intimate thoughts. You have to, it's a very lonely place. And so for those that want to do that, it is, there's no other way to determine if you're fit for purpose unless you give it a try. But the reality is you want to be as prepared as possible and get advice to make sure you really know what you're getting into because it is a all-inclusive, as you just said, role.

In one of the most honest moments maybe, you know, in regards to this topic was when Elon Musk was on, he's on the podcast and the guy asked him about running, you know, I think at the time he was talking about running, um, SpaceX like in the early days. And he's like, and Elon just said like, you don't want my life. Like to do, to run this company, to be the CEO of this company, I'm sleeping on cots. I'm working 48 hours in a row some days. Like you don't want. He's like, you don't want this. Like you don't want this. And that is a conversation that is just, I feel like not had enough or at least not had enough in enough environments where it's like to be a jensen wang to be a jeff bezos to be these like CEO figures that we idolize like when you actually break down what their life looks like

they're not able to be the coach of their little league team if that's what matters to them they're not able to have a consistent Tuesday night date night with their spouse like there's that the tradeoffs are often glossed over for the glory when you know, most people are not cut out or simply don't want the life. They want the title. And then the disconnect between the lifestyle and the title creates all this tension. And now all of a sudden they're looking to make a career move. And this is one of the things that I thought you did well.

And your book was talk about, like, what are some of these struggles that high performers are dealing with when they're in these career transition moments? Like, it's such a tumultuous time. Like, how do they navigate these moments and without fall? apart without, you know, falling into a depression or losing their self-belief for confidence. Yeah. It's, listen, what you just said is exactly right. These jobs, whether it's a CEO or a C-suite or anybody underneath them, in this environment right now, everything is all inclusive. Everybody is heads down. They have more than a full-time job on their plate. And now, of a sudden,

you're thinking about making a career transition, as you just asked. And you may not have ever done it or done it in a long time, or you clearly have never been taught the right way to do it, because there is no, as you know, and your listeners know, nobody in the world has taken a course in college or in graduate school, how to navigate these. Like there's no, there's no course or curriculum. So all of a sudden, now all of a sudden, your heads down, you're trying to start a process that you're not sure how to start, which is exactly why Jeff and I wrote this book, by the way. The origin was during COVID, when nobody could meet anybody in person, every executive was calling and asking, what do I do this, should I do that?

How do I resign? How do I, et cetera. And we've known it forever that there's really no good source. My wife overheard this conversation. And she's the one that said, why don't you write a book because you're giving basically similar advice to every single person. It'll save you having to say it every single time. And that's really where the idea came from. The reality is the best place to start is before you need a transition, before you're thinking about a transition.

We talk about career management and career transition in this book. The career management part, Ryan, is very simple. This isn't rocket science. When you're called, you're happy in your role right now. I call you and I say, hey, Ryan, I have this incredible opportunity we thought of you for. Now, you may not be interested in it, but you haven't gone to the market in a long time to find out how attractive are you in this market. How valuable are you in this market? What is your narrative to package the accomplishments that you've done in the role that you have?

Give it a try, get out there, make relationships, extend your relationships, because when you want to do the transition and really get the, the optionality is the word I'm looking for, whether you go or whether you say, you have built a network of people that you can go back to and people will think of you. So you're not all of a sudden doing it as a transaction. Hey, Ryan, I need your help. And then I don't talk to you again until I need your help again.

That is the wrong way to do it. So what I hear you saying is that even if we're in a spot where we feel good, we feel comfortable, we're not, we're not unhappy. we still need to be cultivating the optionality. Like this is part of the current marketplace that we're in, a continual cultivation, at least to a small extent, of how we're perceived in the market, who we're connected. Like this becomes just part of being an executive,

part of being a business person in today's world. 100%. We talk about it in the book. It's one of the very first things we talk about. In my opinion, it's one of the most foundational things we talk about. There's a bunch of points and advice in the book. This is actually one of the most foundational points, which is saying yes to extending your network. If you just think about it for a second, reframe, you get a phone call.

What most people hear is, do I want that job? Do I like that company? Or am I happy where I'm at? And so they typically will say, no, I don't want to meet that person. No, I don't want to go on that interview. Just reframe it. Instead of an interview, you're just going to meet somebody having a business dialogue to learn about the company, about them, make a relationship. And just think about the compound effect if you say yes, more and more often if you're starting, if the listeners on your podcast are early in career, and they just go meet people because somebody wanted to introduce them.

Guess what? It could be a private equity, someone in private equity. It could be somebody in venture. It could be somebody on a board. It could be like, it doesn't matter who it is. is just go build the network and just learn, ask them questions. The common mistake after you say yes to meeting is, oh, they're going to ask questions and I'm going to answer them. That's not it.

It's just have a dialogue. Come with a point of view. Like talk, get to know them and build those relationships when you don't need them because it's just the way it works today. If your heads down and you spent, I don't know how many years doing what you do and you do it really well, but you've met nobody outside your. company or your industry. And all of a sudden, now you, to your earlier question, you want to make a career pivot, like you're kind of limited now. You've got to start from scratch at that moment versus start now, manage the rest of your career. However long it is, whoever's listening, however long it is, say yes now and be strategic about it. Don't just wait for someone to offer you

to introduce you to somebody. Go ask, Ryan, say, hey, Ryan, you know, I see you're connected to this person. I'd love to get to know them, him, her, that company, the business model, that sector, whatever, just show curiosity and be strategic about it. Do you think that that's being, like, disingenuous to your current company at all? If you're saying yes to those things, should someone feel bad about that? I mean, and a reason I asked this question is, I'm going to say recently, but it was probably like three or four months ago, I had someone reach out and say, hey, like, I like where I'm working. I'm not unhappy.

I make a decent enough salary. Like, you know, there's no real problems, but I got this offer or, you know, offer to have a conversation. And there was almost like a morality issue they were dealing with internally of like, if I say yes and I go talk to this person, am I cheating on my current company that I'm not upset with by doing that? Is that irrational? I don't know if it's irrational. I think it's human nature to think that, honestly. I think that's kind of human nature. The reality is it's not accurate.

Like, you're not married to your company. It's a business relationship. They hired you to create value. If you weren't creating value, they would fire you. It's in your best interest and your company's best interest to make sure that you're building relationships in the ecosystem, in the industry, because who knows the value those relationships could have. For instance, somebody in, let's just say,

the tech software sector wants to go meet another CEO in the same or adjacent sector and learn about the company. There's nothing wrong with that. Like it's, yes, if it's a direct competitor, be very careful. You don't want to have it obviously be thoughtful, be purposeful, that you're not showing up at the company and being seen at another company. be very careful about all of that. But having a discussion over the phone or a video conference and just learning, remember, just because you say yes to a conversation, nobody's offering you a job.

This is where people get super confused. They get way ahead of themselves. Like, the ask is, do you want to meet so-and-so? Do you want to have a conversation with so-and-so? Leave the ask there because that's all it is. It's not an offer. It's not a job. It's nothing other than, do you want to meet someone?

And the answer is typically we say yes. Now, clearly, just going back to the very first comment you made, these leaders, again, whether it's CEO or C-suite, they're really heads down. They have limited time. So be thoughtful and mindful about who you say yes to and be deliberate about why you're saying yes, rather than just, oh, I like this person. Is there somebody on the board that would be useful for me to get to know? Can I keep the optionality in this discussion long enough to?

to meet that person? Can I keep the optionality long enough to meet one of the investors? Can I keep the optionality long enough to meet the CEO? Or to learn about it? That's not cheating on anybody. The reality is that could be super hopeful for your company, potentially if you don't go

and don't make a move. I wanna go back to this comment you made, achieve something. This is a really powerful idea, in my opinion, because to your point, if you're chasing money or you're chasing titles, it's very possible that you're being hired on potential, right? And that seemingly only works for maybe one, maybe two jumps, and then

people start asking the questions, like, what have you actually done? So, like, what is the true downside to not, you know, making your mark in a position? And how do you know when you've made that mark enough that it could warrant a move, right? Like, you've, like, what is achieving something look like? And I know that very broad. I get that that's a very broad question. Like, what does that look like in theory to say, okay, I've established myself enough here that if a new opportunity were be presented that I'd want to move, I feel like I could stand on this work and it's not just like a stepping stone. Yeah. I think a lot of people look at it like, well, in the tech sector for sure, and in a lot of sectors where there's equity,

vesting kind of is a good guidepost for a lot of people. Equity is all over the place. I would say the normal equity distribution is four years. That's kind of typical. And you hear a lot of executives think about moves at kind of that point because their equity is fully vested if it's that kind of timeframe. That's one reason people will start to look. Another reason people will start to look is they, they,

they've achieved what they came in to achieve. It could be an M&A event. It could be an IPO. It could be a lot of different things. It could be a stage of growth that they were asked to step in for. And so some people, they know what they're good at. And they're really specialized at this period of growth. They're not the zero to one leader.

They're the scale leader. Or they are the zero to one. They're not the scale. Or at the point when you get a little bit later in your career, Jerry Elliott, you read her comment, which I liked, although I will give a caveat to it. The way she framed a career was the first 30-year career, you do whatever you have to do, the second 30-year career, whatever you need to do in the last 30-year career, whatever the hell you want to do.

And I told that to my 25-year-old son, and he read the book, and his comment back to me was, that kind of feels old-school, Dad. Like, we don't think this generation doesn't think like that. because we can do anything we want with new technology. And I thought that was a really interesting reframe that he gave because it's kind of true. When you and I were 25 years old, you couldn't really do, you could, it was harder to start a company. It was harder to get things launched. Today, anybody can do just about anything they want.

So it's, there's a lot of reasons. I would just, I would tell you there's a lot of reasons that people want to make the change. I think that's a really good point. I know, you know, I was, when I was first graduated from college was 2003, and at that time even, even though like the dot-com bubble and everything that was going on in Silicon Valley with the, you know, the internet and all that kind of stuff was there, I'd say the rest of the world still didn't think of entrepreneurship as like a positive quality. It was like, oh, you couldn't make it or hack it in like a real company. So you had to go like try to start your own thing. It was almost like, it was almost like this weird group of weirdos, I guess. But, um, and then now it's like, if you're not an entrepreneur or haven't had at least one

entrepreneurial experience in your career, somehow you're like, that means you're not capable or you're just, oh, you just gave up and went and worked for a big company. And like, I think I may even have in my early 30s fallen into that a bit, like, like believed that idea that if you weren't trying to start your own company or be an entrepreneur that somehow, you know, you've just given up by going into corporate America. And now at 45 going on 46, I think I've come to a more balanced position where it's more about just knowing who you are, right? And I'll give this idea.

And then I'm very interested in your take on this is like, it took me a long time to realize that I'm a wartime general. Like if everything's going great and you're established and 3% growth, is awesome for you. Like, I'm just not the right executive for that type of company, just the way my brain works, the way I operate. And I've tried that and been unsuccessful and then looked at myself and be like, why couldn't I make it? Well, it's just not, to your point, not my personality. How does someone, so take your son, 25 years old, right, coming up in the game, like, how do, how does that 25-year-old kid start to figure out?

which version of executive they are like the zero to one the scale the you know sustain and grow the enterprise like how do you start to figure out what your place is yeah i listen i'm i'm i'm a dad on this question not an expert so i let's just be real there's probably better experts on this particular question we we as you know we're we're focused on a different audience but my i will tell you as a dad my advice to my my son is is where you can learn the most, have the best impact, and grow the most. It's not the normal way I hear his friends talk and is all about money. And it's literally all about equity, all about money.

And there's this whole FOMO thing of I'm going to miss out on going to this LLM company or this hot startup or this whatever. And the reality is if it was that easy to pick a way, winner, like everyone would pick it. And the reality is, some are maybe easier than others and more obvious than others, but the reality is then they are that much more competitive. So you're competing with the entire world. And they're going to compress you. So if you were a senior executive at whatever company and you want to all of a sudden make a decision to go into whatever direction and you happen to want to go to one of these hot startups, you're going to get probably

put on a individual contributor role, a manager role, a director role, just because they can. And it's that much demand. And it's just such a simple demand supply kind of rule that when you're that attractive, everyone wants you so you can compress everybody. So I think coming back to how do you decide, don't decide on money. Like that is like the wrong thing to do. What if you, if the listeners on this podcast are earlier in career, go build capability. Go build relationships.

Like these, the relationships that people build right now, like my son. And I tell them all the time, make sure that you are. whatever you do, wherever you are, that everyone says things about you when you're not in the room that are positive. If you give them reason to say things that are negative, they're going to, A, they're going to say it, and B, they're never going to forget it. I just had a recent situation where Jeff and I are working on a big branded public company CEO search on the non-gov committee chairman heard a name that came up and said, nope, wouldn't want to engage that, that person. I knew that person 20 years ago, and that person was a jerk.

And that person, just think about it for a second. Any of your listeners, if you're somebody that does something to make someone mad, immoral, unethical, sneaky, whatever, nobody around, everyone's going to see it and know it, and no one's ever going to forget it. And just know that's the case. Yeah. We definitely, we definitely. do not consider

I think it's very easy to get caught up in like this specific situation, right? My ex-counterpart doesn't like the way I communicate on Slack and, you know, that person's this. And, you know, you get caught up in like these little fights. And I feel like we lose perspective in the moment of how, like, is it really important to my career that I like have a battle with this peer in an organization

over whatever this topic is, or do I just like maybe suck up a little bit of my ego for a second and just like get through this, solve the problem, and be seen, you know, maybe I don't love the way I'm being talked to, but we accomplish the mission, and that's what people are going to remember, or we could accomplish the mission,

but because it was done through all this conflict and infighting and backs, now all of a sudden that's what people forget that you achieve this big goal, and all they think about is you're this troublemaker. And it's simply because we're not, like, how we get there is as important as getting there. Does that seem reasonable? Or is that right? Yeah, we talk about it as you know, we talk about it in the book. The how you get there, especially at all levels of your career, at all stages of your career, at the senior level,

100%. Where, you know, think about it. If you're a CFO and you're signing financial statements, you better, as a CFO, you better have a very clean track record of ethics and, and just honesty, transparency, et cetera. Like, how you do things matters a lot. And it does get lost on people. They just see the end goal. Like, I want this IPO or this vest or this title, this role. But remember, relationships are currency.

And you want to build as much of that currency as you possibly can to have people say, I mean, I often say the best thing somebody could ever. do for me is say something nice about me when I'm not in the room. That currency is more valuable than my paycheck. Because if they aren't saying nice things about you or me or any of your listeners when they're not in the room, you and I will never know what's being said because we're never, we're never told. But your goal should be, your listener's goal should be, have people say things great about you when you're not in the room, how you did it to your exact point. Be flexible. let go with the ego. Like I had a guy called the other day and he's stepped out of his operating role.

And now he wants to go be a private equity operating partner. And I asked him, I said so, and I don't want to say what company is with, but it was a company that mid-tier at best in terms of how it's perceived in the market and by other leaders. and this individual seemed to think he could demand like a premium price for his for his services to be a operating partner. And I had to say to him, I said, listen, do you understand like the way the brand that you came from is looked at is at best a mid-tier brand? It's not a premium brand. It's not a pure play AI company. It's not one of the well-respected brands in the industry. Like you're going to have to go really understand kind of how you're perceived in the market because,

you have a perception that you should be demand a premium price just because you had a title in a company with scale. And it took him a while to figure out, you know what? I did have an ego. And I thought I was because I had this title and this scale of company, et cetera, that I could demand this premium price. And the reality was he called back. He said, you know what? I really appreciate it because your feedback pointed out the ego that I had, I just had to let it go. And that is, it'll get people in trouble every single time.

You and I probably have had issues with it over the course of our careers. Most listeners have. Anybody that's competitive has an ego by definition. And so it's easy to say let it go. It's super hard to do. But that is we're hired in companies or we start companies. We're working in companies to grow them, build value, sustainability, generational companies, etc. It's not just about the money.

Yeah. I actually, I did a TEDx talk in 2025 on this exact topic. It was called Stop Living a Life You Didn't Choose. And the whole point of the, the whole point of what I was trying to convey was exactly what you just said and that I had allowed my ego to push me in a direction that I didn't want and found myself in a situation that was not good that crushed myself. self-belief simply because I was chasing title and money because that's what my ego told me I needed to have and I hated every second of it and it wasn't the company's fault it wasn't their fault right they were paying me a great salary they gave me the title that I wanted but it wasn't the right fit it wasn't the right situation for me in any regard because I had let my ego you know push me

down this path of like well this is what you're supposed to be doing Ryan like you had this and you went here and now this is the next step on the journey for someone in career evolution, yet it wasn't what I actually wanted, you know, but I let that ego just convince me that this is what I should have. And, you know, I don't want to say I paid a price, but I definitely, it was a, you know, if you were to look at my resume, you go, well, why were you only there for nine months? And now people are starting to look at you like, ooh, you know, that's not great. I think you're right that everyone has those moments, but again, it's one of the reasons why I love doing podcasts and talking people like you is like hopefully some people listening to this can, you know, maybe sidestep that particular landmine, you know, by hearing these conversations. On that point real quick, Ryan, I just want to jump in because I think it's a most executives miss this.

either they miss it or they don't place weight or value on it, which is what happens when you make one of those bad decisions that you just described that you made for your, for whatever reason. In this case, it was ego, other case it's money, other cases it's a friend asked me, whatever the reason is, when you're on the other side of that, the question that everybody asks on this side, whether it's people like Jeff or myself or CEOs or whoever, is they question you. your judgment. That's what they question because you have to start with what was the judgment? Like what did I miss? Like because everybody will give you a hall pass, but you need to understand, you need to be authentic and transparent and self-aware. What was the, what did I miss when I took

this role that now looking back, I won't make that same mistake again. You have to call it out. And because that's the thing that everyone really questions. We all make mistakes with our career. All of us do. There's very few people that have just had like what most, I guess, would describe as a perfect career. And honestly, I don't even know what that is other than just somebody is not made a mistake. So we all have, and it's okay. We've all made mistakes in life.

It's okay. Just make sure that you know why you made it, the judgment that you, used to make that because that's what's going to be in question about why you made it. Yeah. I think you're right. And I'll tell you, you know, 10 years removed from that decision, you know, not that it doesn't get brought up very much anymore being 10 years removed. But, you know, now I can say to them like, look, this is the reasons that I made that

decision. They weren't the right reasons. I learned a valuable lesson about how I choose where to work, why I work, what things are important to me. And now I can articulate that and I think it's fine. But, you know, it was like the first job that I took after that. It was a real struggle to define like you had this spot. You were making this money. You had this title, you know, like, what the heck happened? Like, why aren't you still there crushing it? And it is that's, I think you're very right. And I think it's a really important point that like if you can articulate the decision making process, even if articulating that is, you know,

I messed up. Like I, I, looking back, I shouldn't have. done that, I feel like that gives people the peace of mind to say, okay, this person's adaptable. I completely agree. And I'm very glad you brought that up because I don't think people think about that. That it's actually the judgment. It's not just the nine months or whatever. It's like the why did you do it and what is your thought process after. It can even be a potentially a boost for you, especially if you've learned something from it. So I love that. I want to ask you, because this is actually something that I have dealt with in my own career as an executive is very early on in my career, I almost say inadvertently established a public personal brand. I just enjoy being creative. I have to say

I have a podcast. I enjoy writing, you know, on certain social media, I'm active just in creating content, sharing my experience. Okay, all that kind of stuff. And I've developed a brand and a following and that brand, I found that personal brand to, in some cases, be an incredible boon, right? Doors open, people are willing to talk, and that's amazing. But there's a flip side to it, too, where, you know, people will be like, well, how does that play with us? Where, you know, what if you say something crazy that's, you know, contrary to what we believe or what we stand for or whatever. So how should executives manage, think about the cultivation of their personal brand in relationship to their career, if that's something you're doing? Yeah. I mean, this is probably

we spend the majority of the time in the book talking about this, Ryan, which is executives, when they come into a process like this, so they want to think about a transition. A hundred percent of the conversation is about what the buyer, the person at the company, what, problem they're solving, what they want to achieve by hiring somebody. And so it's all about what they want and what they need. And for you to decide with your optionality, as long as you can keep that optionality, is this what is going to motivate you? And is this the right opportunity for you? Your point earlier about the mistake you made that you thought you wanted it and it wasn't what you wanted and you left it a short period time. The reality is,

is what most leaders do when they engage in this process, they come in and talk about their own brand. They don't come in and talk about what they've done and who they are and who they want to be. And no disrespect, but really nobody cares because the only thing they care about is can you solve my problem? I'm going to pay you a lot of money. And in the world that we're in today, the timeframe for making an impact went from years to months to weeks. Like, it is, they don't have time. Companies don't have time anymore to teach you at a senior level what they want and how to solve their problem. They want you, as Fiji Simo talked about in the book, like I thought her quote was incredible.

Like, be clear about who you are, what you believe, and how you plan to contribute. Bring ideas. Show them how you think. Like that is, she made a couple other quotes, but that one was really powerful. powerful because it's just a, it's a point where people get confused. They think they're in front of, if you're hiring and I'm in front of you, oh, Ryan, there's an answer, there's a perfect answer to every one of your questions or there's like, I got to win this or I need to impress you. That's not it. It's like, for your listeners, reframe your thinking. That's not the way to approach this.

It's do your homework on the company. Ask the question. Show curiosity. Show self-awareness. ask what you're solving for with this hire. Ask what the issues were. Have you tried anything? And then use the knowledge because you know your career. Find those examples in your career after you know what they're solving for to give examples to show how you think or have a point of view. But don't go in saying, this is my brand.

This is what I can do. This is what I've done. Nobody's hiring you for what you did at whatever company before. They're hiring you for this company to solve this problem. That is such an important point. And it's so easy to just sit down either literally or figuratively and be like, look how amazing I am. Look at all these amazing. Look all my awards behind me.

Look at, you know, look what I've done. And have the other person go, so what, right? I'm trying to paraphrase you. This, I'm not holding this as my original thought. You're selling what you can do for them. Right? So it's not, look how amazing I am. it's, oh, that's the problem you have?

Well, in my previous job, we solved that problem by doing X, Y, and Z. And now they can, like, it's kind of like, and tell me if this is wrong. It's like, you're trying to frame it so they can see you, like, at the board meeting or at the executive leader. Like, you can see them sitting there with you and feeling great about it. Like, that's what you're, you're trying to, like, paint them a picture of you in the company, not look at this amazing stuff that I did and all the words I get. So just hire me because I'm awesome, right?

Which is the way a lot of people try to pitch themselves. Yeah, 100% correct. I love the way you reframed it. I often tell executives going through this process, you want the person on the other side of the table to visualize you in that role in that company. That's how you want that to leave that discussion. The only thing I would add to what you just said is, and this is, in my opinion, a best practice, which is question, by. asking questions, this is what I don't think a lot of people appreciate, you can show me how you think by the questions you ask versus you telling me what you think. And when you ask questions,

most people want to jump immediately to let me tell you about me, let me tell you how I solved this problem. I just am a firm believer that you can't just keep asking questions. You have to put a point of view on the table at some point. But it's all about engagement. Remember, all these are just, these are executive conversations. It's someone makes a comment. I ask maybe for clarification. I ask, I ask a question because I want you to know that I understand what you're saying. I ask a question because I want you to know that I understand that issue. I've seen it. So if, if that's the problem you're having, have you guys tried this? Or what was the experience or what did you get your whatever metric up to.

Like those types of questions tell the person on the other side of the table. You know what you're talking about. And you've seen you have a best practice and you know what good looks like. From the other side of the table, right? So you have, you have an executive coming in. What are the like top three things today? Like what am I prioritizing if I'm the, you know, say I'm the CEO and I'm bringing in a a CMO, right, just for purposes of conversation.

Bringing in a CMO. We don't have a CMO or, you know, we, we had a CMO. They left. We're trying to replace. When I sit down with them, more than just like, can you do the job? What are the characteristics that you see being prioritized most when bringing in executive, assuming that person has all the credentials to do the actual work? Yeah.

I mean, to do it. So what's fascinating is how quickly this is all changed. I mean, if you would have, if you would have, If you and I would be talking five years ago or 10 years ago, the answer probably would be different. Today, and it's regardless of C-suite, it's almost ubiquitous to everybody. CEOs want adaptability. They want agility. They want the person that shows curiosity, the learning, the ability to learn quickly.

In this world, as you and your listeners all know, the world is moving way too fast. And so you need to show an aptitude of learning at a pretty high rate. And you need to show that self-awareness by asking questions because and being vulnerable. I mean, it wasn't too long ago where a leader, if they felt they wouldn't expose a gap in their capability set for a new role. they wouldn't expose a piece of experience that might be beneficial or essential for this new role. Today's world, call it out. I'll give you the simplest example on this point. There was someone who called me was going to be a chief sales officer, a CRO for a company a couple months ago.

And we talk about this a lot in the book, which is anytime one of your listeners are going, to step into a role for the first time that they've never done, at a senior level especially, ask for a coach as part of your negotiation. And the reason why, this executive said, I said, he was asking about his negotiation, I said, well, have you asked for a coach?

And he said, well, no, they would think I'm weak or they would see that as a weakness. And I laughed, because I said, wait, they know you haven't been a CRO. Like there's no surprise. They've seen your resume. They know you haven't done it. And so think about it from this perspective.

If you or them, they would want you to come and ask for a coach because it shows that you're self-aware. It shows that you know that you have a gap. And guess what? That company, they don't want you to make rookie mistakes. The chances there's probably a 99% chance you're going to make rookie mistakes because you've never done the role before. You know a lot of people in that role.

but it has nothing to do with it. You've never done it. So to minimize the mistakes and to protect their investment, they're going to spend, I don't know, $100,000 on a coach, whatever the number is. But if they can avoid making a rookie mistake, it's going to cost them a million or maybe some other bigger issue, that is well worth it for them. So it's just, it's a, it's a vulnerability that is a sign of strength. shows that you're aware and that you're present. So those are a couple things. I mean, the other thing I guess I would I would call out is if almost every company in the world is going through some transformation right now, you know it, your listeners know it. Soft skills matter a lot right now. And the reality is there's a lot, there's a tremendous amount of

stress in the system right now. Everyone's stressed out. Everyone's working too hard. There's a lot of companies underperforming. There's a ton of pressure being put on those companies by those boards and investors. All those executives are getting squeezed at all ends right now. But try, your listeners, try really hard. It goes back to the reputation comment we made a little bit earlier. Soft skills matter a lot right now because everybody is being asked to morph their mind, body, experience into things they've never done before, at a pace they've never done before.

So those are the things that I think matter a lot right now. I love it. I want to finish our conversation selfishly. I told you in the green room that I signed my first book deal. Very excited. Easy mode will be coming out in September of 2027. So lots of work still to do, but very excited. Congrats.

You've just published a book, obviously. you know, like what surprised you about the process? Well, if I can reframe the question of the biggest surprise about the book for me in a pleasant way. Jeff and I were asked early on, like, what is our goal or objective with this book? And clearly it was to share the advice that we give to executives because there's nothing in the world like it. And we hope to go to business schools and teach it. We hope to do a lot of things with it. We're going to start, I think, our own show-up-to-win podcast to get this democratize, basically, this advice is kind of the easiest form.

So that was, that's the market hydric serves. That was the core purpose. However, Jeff has young kids that are entering the work world. I have young kids. And I think both of us felt that if this advice that we're offering to senior executives could be useful to the next generation of leaders like our kids, and et cetera, then it would be a home run. And I will tell you, that's one of the biggest surprises that I personally have had over the last few months.

The book was published, as you know, July 7th. The amount of calls, messages, emails that I've got from senior leaders that have said, Kelly, I've loved reading the book. In fact, I bought it for my kids. That to me is, like, as anybody that's listening that's a parent on your your podcast and you know, you have, you have a son, I believe, right? Two, yeah, 12 and 10. Yeah.

There's nothing as a parent. There's no parent on earth that would say that helping my kids is probably the best thing you could ever do for me. And every parent in the world would be completely happy if there is, if all of us helped each other's kids. We hope this book helps the kids, the next generation leaders, which is the feedback that we're getting. And I love that, man.

And I agree with you. I think leadership is something that is not talked about enough early in life. You may get a little of it from maybe like a sports perspective if you're involved in youth sports, et cetera. But they're not teaching these topics in school. And, you know, what I enjoyed about the book is just it feels very tangible, very real. and from my own 25 years in this environment, it mirrored the experiences.

And there were parts where I was like, shit, I wish I knew this 15 years ago. So I completely agree. I'm so happy that you wrote it. I'm so happy you were on the show. Besides links to the book, which obviously, guys, whether you're watching on YouTube, listening wherever you listen, scroll down,

I'll have links. Where else can people get involved in your world, in Jeff's world, so that they can follow along with your journey. Yeah, thanks, Ryan. First of all, thanks for having us. I'm sorry Jeff wasn't able to be here, but we're grateful to be on your podcast.

You have an incredible audience, incredible listeners and viewers. LinkedIn is probably the number one place for Jeff and I. We have a show up to win book.com website as well. That's at the end of the book, you can, you can, can take a look at that. But I think it's right now, it's really LinkedIn. I mean, that's kind of the, we're posting a lot on LinkedIn right now. We haven't gone into YouTube or anything else

at this moment, just given the audience that we're serving. But really appreciate your listeners following and hope they enjoyed it. It's been a pleasure. I appreciate you so much. I love the conversation. And I wish you nothing but success. And hopefully everybody in the world buys the book. And when you write the next one, I'd love to have you on the show. That sounds great, Ryan. I look forward to it. Thanks, Callie. Cheers, man. Take care.