A lot of people spend plenty of time thinking about how to succeed in their jobs, but far less time thinking about how to choose the right jobs in the first place.

In this episode of Career Sessions, J.R. Lowry sits down with Kelly O. Kay, managing partner at executive search firm Heidrick & Struggles and co-author of Show Up to Win: The Insider’s Guide to Getting the Career You Want.

Drawing on decades of experience advising executives and companies, Kelly shares an insider’s perspective on how to manage your career more deliberately. He explains why you should take the recruiter call even when you’re happy where you are, how to test your value in the market, what makes a candidate’s story compelling, and how to evaluate whether an opportunity is actually right for you.

J.R. and Kelly also discuss why internal candidates sometimes struggle against outsiders, how to recover professionally after being fired, the subtle ways candidates sabotage themselves during the hiring process, and why your reputation can follow you for decades.

Whether you’re actively considering a move or perfectly happy in your current role, the message is simple: the best time to manage your career is before you need to.

Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/kelly-kay/.

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Watch the episode here

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You’re Always In The Job Market: How To Manage Your Career Before You Need To, With Kelly Kay

Too many people I know spend a lot of time thinking about how to succeed in their jobs and probably too little time thinking about how to choose the right jobs in the first place. For example, when should you take a job and when should you leave it? What are you worth in the market? How do you tell your story in a way that makes someone want to hire you? Perhaps most importantly, how do you make sure that the job you’re trying so hard to get is the right one for you?

My guest has had a front row seat to thousands of those decisions. Kelly Kay is a managing partner at Heidrick & Struggles, one of the world’s leading executive search firms. He has advised hundreds of CEOs and board members and thousands of senior executives on some of the most consequential career decisions that they’ll ever make. He and fellow Heidrick managing partner Jeff Sanders have now distilled what they’ve learned into a great new book, Show Up to Win: How to Land the Leadership Role You Want.

We’re going to talk about how to manage your career more deliberately by learning how to assess your value, tell a compelling story, and navigate the hiring process. We’re also going to talk about when you should take the job and when you should turn it down. I’m J.R. Lowry. This is Career Sessions. Let’s get to my conversation with Kelly.

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Kelly, welcome, and thanks so much for joining me.

Thanks. It’s a pleasure to be here. Thank you for inviting us.

I’m looking forward to this conversation because anytime I get a chance to talk to somebody from the search world, I know I’m going to learn a lot and I know our audience is going to learn a lot. You’ve got a new book out with your partner, Jeff Sanders. Let’s dive into some of the topics that you cover in the book. One of them is around this idea of knowing when it’s time to move. You guys argue that some very successful people are pretty unsystematic about how they manage their careers, including deciding when it’s time to leave a job. Talk a little bit about that.

Why Career Management Can’t Be Episodic

One of the things Jeff and I frame this book is a very practical guide for career management as well as career transitions. The career management part is something that most executives just think about when they’re looking for a new job. That’s typically kind of the way career management happens for most executives. If I want to change jobs or if I’m getting recruited, that’s when I’ll start lifting my head up. It’s episodic in that way.

The reality is, there’s a very easy way to do career management, which is to say yes to phone calls and say yes to get introduced to others. Be strategic and thoughtful about it so you don’t say yes to everything. You’ve been an operating exec, senior exec for many years yourself. These roles, especially in today’s world, they’re all encompassing. It’s hard to find the time to do it, but it’s valuable to do it because it’s like a compounding effect of relationships that you build over time if you start early enough in your career. At the end of the day, my advice and Jeff’s advice start now. If you haven’t said yes to many conversations, start now and just start building those relationships.

I completely agree. I also think there’s times where you take that call and it sparks a thought of, “Maybe I’ve been missing something that I could have been eligible for.” How do you make sure that you are thinking about that decision of whether you want to stay or go or consider other things in a more systematic way, more comprehensive way?

There’s a number of things and frameworks that we talk about in the book for evaluating. Is the time right? One of the things we talk about, we list twelve different common things we hear why people want to change jobs. Everything from, I’ve plateaued, to I’m out of ideas, to there’s been a leadership change and everything in between. The reality is that in order to have success to talk about, you need to stay at a job long enough so you can point to accomplishments in a role. That’s just the ante.

Testing Your True Market Attractiveness

If you haven’t stayed long enough to achieve something and show results that you don’t have a lot to talk about. That is probably a very early filter. I’ve been here long enough to point to results that are impressive. One of the frameworks we use in this book is, I refer to it as the ABC framework, but it’s labeled in the book as the company and candidate attractiveness framework. It was meant to give leaders a lens to say, “In this market, who am I attracted to and who’s attracted to me?”

Most times, leaders who are looking for a change and trying to figure out if it’s time, which is the question, they’re unsure who they’re going to be attracted to and who’s going to be attracted to them. They miss the second part of that. They think, “I’ve had this success therefore I can get it. I want to get a job at this company or this brand or whatever.” The reality is that companies that they view as aspirational may look at them as a C quality candidate, not because they’re not a great executive, it’s just that they don’t meet the requirements of what the company’s looking for.

Fit certainly matters. How do you figure that out when you’re a candidate? A lot of times people have unrealistic views of their market value, either too high or too low or breadth of their market attractiveness, I guess I would say.

It’s a great question and I hope your readers will listen to this part because it’s one of the things that most don’t do the right way. The advice that we give is up to the leader to figure out how attractive that leader is in this market and to what type of company. As a leader, you may say, “I would view these brands or these companies as aspirational.” Forget the role for a minute, just the company itself. You might win 20% of those because it’s a long shot. It’s aspirational.

B quality companies that I would find interesting, I should win probably 50/50 of the ones I’m competing for. C quality opportunities to the executive would be ones maybe where it’s a company in their space and similar domain. Maybe a similar role. They should win 80% of those opportunities they go to interview. Go out and have conversations. Find out who is attracted to you and who are you attracted to? To your point, sometimes when you take these calls and you start to hear things and you start to meet people, your mind might shift to what you didn’t even prepare or expect to happen.

You, all of a sudden, become interested in a brand that you didn’t think of, a role that you didn’t think of, etc. A quick way to summarize that, is it’s up to the executive to go find out how attractive they are and how valuable they are in this market. Different companies are going to pay different comp packages based on the capabilities that you’re going to bring and the problems they’re asking you to solve.

You’re arguing essentially, Kelly, don’t just take the call, but go do one round of meetings.

Protecting Your Executive Optionality

I would argue to do at a minimum, yes. It’s about, as I said earlier, being strategic. When you do take that first meeting, the whole argument that Jeff and I make is keep the optionality on your side. Most leaders don’t think of a process through the lens of optionality. If you think about it, the goal of a leader is to take the time to go meet somebody. The goal is to have the person that they’re talking to want to spend more time with them, want to learn more, want to engage further so that the leader can decide if the leader wants to invest that time.

At the end of the day, we see a lot of times where leaders will approach a meeting and they’ll put up demands like, “I won’t move. It has to be paid this much money. It needs to be this title.” All those are just blockers. Those are all things that can come down the road. Go meet somebody. Go have a business discussion about what the company is doing? What are they trying to solve? What’s the purpose of why they’re looking for this role? That is the starting point for the discussion. What it’s not is, “I need this much money. I won’t move. I need this title.” That is definitely the wrong way to start a discussion.

That’s pretty counterintuitive though to the way that a lot of people approach those conversations, at least from what I have experienced, because they feel like it’s a little bit like round one of a speed dating process in a way. The idea is to figure out relatively quickly whether there’s something there.

We’re talking about the leaders that we place at Heidrick and in this industry are at the peak of their careers. It’s not about a volume of meetings. That’s not what this is about. It’s about trying to figure out, “I know enough about this company. I know enough about the sector. I know enough about this business model.” That is qualifying enough. If you don’t know some of the people, the CEO, the investors, the board, etc., are all good reasons because it may not be about the job that you end up winning.

It may be about, more importantly, the relationships that you build in the process. Remember, as these leaders show up well in these discussions, the company who has that discussion and was impressed by the leader, how they showed up, are going to go back and tell their HR leader, their CEO, their investors, “We didn’t get J.R for this role. He declined to continue the discussion, but he’s somebody we should all keep an eye on because he’s amazing.” That is what we want.

Certainly, that’s what you want. I want to come back to something you were talking about a minute ago, Kelly, in terms of A, B, and C grade companies. How should somebody, I guess in the context of managing their career, think about, “I could go get a job at this level in an A company, and I could get one at this higher level in a B company, and probably this higher level at a C company?” A lot of people would probably say, “I’d rather have the most senior role in the C company.” You guys would probably argue that it’s more nuanced and complicated than that. I’d love to get your view on how a candidate should think about company quality when they’re thinking about their options.

Executive Career Management: Do you know who’s attracted to your skill set in today’s market? Stop guessing your value and start testing your optionality.

Ironically, I hear in this market and you’re starting to see it, CEOs, former CEOs are stepping back into individual contributor. I see roles in high growth, hot companies. Most leaders, accomplished leaders, would rather be in a high growth company that is performing incredibly well than be a senior leader at a company that’s stagnated or flatline growth or a major turnaround. Those, at the end of the day, are very difficult. What we hear is that they’re not fun. The fun assignments are around growth, and that’s what the best leaders are looking for is high growth and huge TAMs.

It may be a little bit counterintuitive if you have the trade-off of a senior role at a company that is less interesting to you, versus stepping back a level or two at a company that is growing and new opportunities are being created every day. Look at some of these LLM companies, these new frontier companies. Imagine if you were a senior executive. If you went in as a junior leader, chances are in twelve months you would be a senior leader again because the opportunities are just exponential. That is the way the best leaders think about it.

If the growth opportunities aren’t there, the LLMAI companies are an extreme example. If I’m looking at two companies in the same industry, we’ll say they’re both growing roughly about the same amount. How about the optionality that going to an A grade company gives me, versus the optionality of going to a B or C company that may have roughly the same growth, but just not the same quality and prospects?

Removing Emotion From Career Decisions

One of the things that we put in the book is how do you eliminate or reduce the amount of emotion that goes into deciding between multiple opportunities? We list an example in the book, which is we talk about identifying for each leader, how do you define what a quality company is? How do you define what a quality role is?

Thirdly, how do you define what a quality offer is? What we talk about in the book and the framework that we offer is very simple. For each leader, this will be different. It’ll be bespoke and unique to each leader, but identify the 6 to 8 attributes that you as a leader would feel are the priority attributes for your definition, your unique definition of what a company is, and your unique definition of what a role is, and your unique definition of what an offer is.

When you’re in discussions and you’ve boiled your opportunities down to two competing offers or opportunities, as you just laid out. Hopefully, you’ve been able to evaluate both of those against the criteria that you have set at the beginning of your process. Now, it’s a framework only for you, J.R, or for the leader. It could change. It’s not meant to be shown to anybody, but where it is useful, whenever asked, because this is a common question by a company. What are you looking for? What is it you’re looking for?

You could easily now come back and say, “I’m looking for the highest quality company.” They’ll say, “How do you define that?” You’ve already done the work. You can say, “These are the types of attributes to me,” and you are much more prepared for this discussion rather than keeping it all in your head, which 99% of executives do, and relying on the emotion.

Let’s face it, when you’re being pursued or there is interest in your candidacy, it’s easy to get caught up in the emotion. We see executives make decisions around the emotion. If you can eliminate all the emotion or as much as possible, you can keep it focused on the attributes that you believe are authentic to you for the right company and the right role and the right comp package. You’re going to make the right decision.

Having that level of clarity is very helpful. Most people don’t. That’s probably where they get themselves into trouble because they are thinking about titles, more superficial aspects of things. Not so much what they want it to be like and feel like day to day.

That’s an overarching theme of the whole book. The feedback that Jeff and I and Heidrick have been receiving is the intentionality. It’s purpose-built career management where you’re doing things deliberately, intentionally, versus randomly accepting a call that you didn’t expect from a recruiter or a company and you took it. Next thing, you quit your job. The reality is, you didn’t test your value on the market. You didn’t test your attractiveness on the market. It may have been an old colleague or a friend that traded on loyalty or guilt or whatever, friendship. There’s a lot that just happens by randomness and by serendipity. It does not have to be that way.

There’s another point in this process that you guys talk about that’s important, which is getting into the heart of the interview process and being able to tell your story.

This is an important part of this whole discussion because telling the story doesn’t happen just when you’re interviewing with the company. It happens when you’re interviewing with people like Jeff and myself or colleagues in the industry. It happens when you’re getting a strategic introduction. One of the concepts we introduce is a strategic introduction. Anytime you meet somebody, it could be in the process or seemingly before the process.

It’s how to understand the buyer, the company who is interested, or the person you’re speaking with who’s representing the company or individuals looking for talent. Understanding what they want, understanding what they’re looking for, and why they’re looking for it. Get curious and make sure that you are clear on what the requirements are, the capabilities, the experience that they’re looking for before you start talking and telling your story. Your story has no relevance if you don’t know what you’re telling it in relation to.

Step one is just understanding what the company is looking for, such as experiences, capabilities, etc. You can then tailor what experience and capabilities that you bring to the table. It could be from the job that you ran or the most recent job, or it could be from a job or two ago, because the reality is, you’re trying to find and map the most relevant experiences and insights into what they’re most interested to hear about. Not, “Let me just give you ten minutes of a monologue of who I am and where I came from, etc.”

One of the quotes that I love in the book, there’s many that I love, but one is from Fidji Simo for OpenAI. Her comment was, “Be clear about who you are, what you believe, how you think and plan to contribute. Bring ideas. Show them how you think.” That quote kind of sums up how to show up to these discussions. It’s not the title, the comp package, etc.

You’ve heard a lot of these stories in the course of interviewing candidates. What makes a compelling story?

The number one thing that will make a compelling story is how well have you listened to what they’re looking for? It has to start there because that’s the beginning part of it, then how well does your experience match what they’re looking for. There are many times and I would say the majority of the time, especially if you’re interviewing for a role you’ve never had. You could be a C-suite level executive interviewing for a CEO role for the first time or somebody not on the C-suite interviewing for the C-suite.

It’s about making sure that even though you don’t have the most relevant experiences because you have not done that role, it’s making sure that you are at least asking the questions at the altitude and the relevance of the role that you’re interested in trying to win. The common mistake is that people will use the lens of the role they’re in to talk about the role that they’re trying to aspire and elevate to. They have to get mentally adjusted to the attitude of the role that they’re trying to win.

I’ve said many times to many leaders, it’s one thing to know how to talk to a CEO if you’re not a CEO, but learning how to speak like a CEO is vastly different than learning how to speak to a CEO. You can go down the hierarchy of roles. It’s the same concept, which is they just need to figure out how to be the most compelling for the role that they’re talking about based on the requirements that they’re looking for.

There’s a high degree of empathy that’s required in that. You have to put yourself in the shoes of the person who is looking to fill that role and think, “What do they need to see in me?” A lot of people, even the ones who are practiced at telling their story, spend a lot of time thinking about, “How do I make myself look as smart or as technically capable as possible?”

Executive Career Management: When recruiters come calling, emotion can cloud your judgment. Define your non-negotiable career attributes before you enter the room.

It’s true. It’s one of these misnomers about interviewing, and we’ve all kind of been raised to believe that when we interview for a role, that it’s a competition and we need to win. As an interviewer, I ask the questions and interviewee, you answer the questions. That is just not true. The reality is that an interview is nothing more than an executive discussion. It could be at the senior level that we just talked about. It could be at the mid-level, even at the entry level. It’s a business discussion. That’s what it is.

It’s not about using AI to get the perfect answer for a question and memorizing the answer. As we all know, there’s no authenticity to it. The second somebody catches that, they’re going to ask one follow-up question and then the interviewee has nowhere to go. The reality is it’s just being authentic to each individual and engaging in a business discussion. That’s what it is.

How do I handle situations where I’ve had some kind of failure? I could have been laid off or I could have had something not go well in my past and I get a question that goes directly at that because somebody’s familiar with that experience or they just ask about something where they want me to talk about a situation where I’ve failed. How do you answer that question in a way that’s not going to be self-sabotaging?

Taking Control Of Your Exit Narrative

Probably one of the things that I’m most interested in is the book. I’ve referred this chapter essentially to so many executives over the years who have been fired or let go. The best thing you can do as an executive is get ahead of the narrative. What I mean by that is if you’ve been fired, there’s a human condition where most leaders want to get back into a role as quickly as possible so they can show their other employer that they’re of value and they are attractive to somebody. That’s the worst thing somebody can do.

The reality is, if you have been fired, it’s best in our opinion to take the time, process what happened, and give it some time if you can afford to stay out of the job market. Now, obviously finances matter for every single human. There may not be enough luxury with finances to do this the way I’m going to articulate it, but there’s probably a middle ground somewhere, which will take at least a few weeks to process, decompress. Most likely, you’ve been in a pressure cooker. If you’ve been fired, you’ve felt the pressure. Not the last day you were there, but for weeks or months or years, maybe.

Take the time to get healthy, recharge, and reconnect. After you’ve cleared your brain and you’re not talking about your former employer, every single sentence that comes out of your mouth anymore, then go back to, I’ll say the 3 or 4 of your biggest critics at the company you worked for. Try and get them to open up and ask them for time to give you feedback. The way you set it up, essentially what you want to do as a leader, you want to get them to feel comfortable and safe to tell you what was being said about you when you weren’t in the room.

The way you set it up is, “I’ve taken time to reflect. I made some mistakes when I was there. Whether you agree that you did, whether you think you did, it has nothing to do with that.” You obviously did because you were fired. You have to admit to each of these when you set up, “I know I made some mistakes. I don’t want to repeat the same mistakes. I’m going to be in the workforce for a long time. I’d love to learn from what was being said about me.”

Now, what we’ve seen when people do that, it’s not easy to do, by the way. I will tell you, of all the people I’ve ever shared that framework with to do it, and they’ve all done it. They’ve all come back and said, “That was powerful,” and here’s why. Once you do that, and if they start giving you the truth, the worst thing you can do in that meeting is to try and correct them. If you get somebody to be open and share and trust, just accept it, say thank you, and not a sentence more. Once you get that, if you do, you have the keys to the kingdom now because the two things, you know what is most likely going to be said about you during references or when you explain what may have happened in that situation.

Think about it this way. Those people that may have been detractors or folks that could have sabotaged your career if they got a reference call, most likely went from Red to Yellow. Maybe in some cases, Red to Green. Simply because you were self-aware. You were courageous. You reached out. You admitted you made mistakes. You listened to what I had to say. You didn’t argue with me. You just took it in. Now, when I go to the company that I want to go talk to, I can say, “Here’s what I did. Here’s what I learned. Here’s what you’ll hear.” When the company goes and does references and back channels you, they’re going to hear just what you said. Now you sound super self-aware.

There’s a lot to what you just said. One is the point about being receptive to hearing it and not trying to contest it, but just taking it in because it shows a desire to learn. The fact that you potentially reduce the temperature of their comments because people will call them and ask about references. The last point is, you know what they’re going to say, and you can come up with your positioning of that when you get asked the question in future interviews but it does take courage.

Anybody reading that has had that experience. Let’s face it, I’ve been fired in my career. A lot of people have. The reality is that it’s the best thing you can do. Think about what’s the alternative, do nothing. When you do nothing, you have no idea what somebody is going to say. The people who are Red are going to stay Red, if not even go Purple. The reality is to do something. At least you have a chance.

I want to talk about internal candidates. I know you do a number of searches where you’ve got one or two or a handful of internal candidates and external candidates as well. One of the things that surprised me in the book is that they don’t tend to fare well. I’m curious to hear, and our audience would love to know, why is that? Why do internal candidates tend to underperform in these hybrid selection processes that also include external candidates?

There’s a couple of very common reasons. One, they might give an ultimatum. They may have been hired with the promise that they are a successor to a role. There may have been an expectation when they came in. For whatever reason, if it’s a public company with fiduciary responsibility at a senior level, CEO level, they’re going to want to make sure that they’ve looked and scanned the market. Even at the C-suite levels as well. There’s some time and expectation with that. It might be expected that’s going to happen.

When they find out they may have to compete for it, all of a sudden, they could offer an ultimatum. We’ve seen this happen fairly regularly, where it’s like, “If I don’t get it, I’m leaving.” It’s just a terrible way to play the hand. It backfires almost every time. That’s one. Two is they become very high maintenance. If you engage an internal candidate too early in a process, these processes take place at a senior level. They take 3 or 4 or sometimes 6 to 12 months. If you engage an internal candidate too early in the process, they’re constantly asking for updates of what’s going on.

At the end of the day, this process of recruiting is a need-to-know basis only. They’re not told a lot other than their own candidacy. They’re not told who they’re competing with. They’re not told where they’re at with the other candidates. They become high maintenance. Pushing both of those aside, the other reason is sometimes they just don’t talk about the job, especially if it’s one that’s going to elevate them. It could be into a C-suite role, into the CEO role, or a role that they’ve not had before.

They look at the opportunity to talk about during their interview internally through the lens of the world they’re in, going back to what we had talked about a little while ago. They’re sometimes afraid to take risks. At the end of the day, if the internal candidate basically says, “I wouldn’t change anything. I would do it just the way the predecessor did it.” That clearly isn’t a very compelling argument. Show some empathy to the context of what the other leader had to deal with and where the companies come from.

At the end of the day, every board and CEO and C-suite is looking for new ideas. They’re all looking for growth. There’s no company that’s not looking for growth. How are you going to grow the company? Go back to Fidji Simo’s comment, bring ideas. Show them the way you think. Those are some things that we see with internal candidates. They just don’t take enough risk in the process. Remember, they have the inside advantage because they know the culture of the company. They know whoever is going to come in from the outside, that’s going to be their Achilles heel. They may bring lots more experience, but they’re surely not going to bring the culture fit, style fit that you would.

Do you think, though, that the bar is somewhat higher for internal candidates? I felt that sometimes the hiring manager and the HR person who’s on point or the head of HR have a bias to go outside because if it doesn’t work out, there’s a higher expectation that it might not work out because you brought somebody in from the outside. It’s almost like it’s a bigger risk, a bigger bet to take an internal candidate and promote them.

I view this whole process as a benefit and risk equation. Every single candidate, it’s going back to the ABC framework we talked about and finding out your attractiveness and your value. Every decision in the hiring process is a risk reward decision. How much risk am I willing to take? What type of risk? It’s not just overall risk. Is it domain risk? Is it role risk? Is it a style risk? What is the risk that they identify?

At the end of the day, boards and CEOs and investors, they want to eliminate as much risk as possible for obvious reasons. They want as much upside and as little risk. For somebody to get the role with a lot of risk, there’s probably a backstory there that is unique because it’s usually the candidate that will have the least risk when you’re comparing side-by-side comparisons with the most upside.

Executive Career Management: Got let go? Don’t rush back into the market on the defensive. Step back, gather hard feedback, and own the narrative before others do.

I want to pull the curtain back a little bit and just talk about what this looks like and feels like from your side. How do candidates hurt themselves from the moment of that, even before the moment of that first outreach potentially from you all the way through the process?

There’s a long list, which is why Jeff and I did want to write this book. Let’s just go through a few of them. I’ll give you a few obvious ones and a few ones that I’ve seen in my career. They’ve never been repeated, but it’s hard to imagine they happened. One is they talk too much. When you’re in a discussion, an interview process, be mindful of the engagement. I don’t want to call it human nature, but we’ve all been programmed to just want to sell.

I’m selling you. I want you to know how great I am. I want to tell you how great I am. At the end of the day, nobody tells anybody how good they are. Let the data tell how good you are. Let the information you’ve achieved, the results you’ve achieved, talk for you. As the person interviewing, you decide if the data I just gave you was compelling versus like, “J.R, I’m a great guy. You should hire me. I want this job.” That’s not compelling.

Talking too much and not being relevant with what you’re talking about for the person who is hiring, because they’re a buyer, let’s face it. You’re a buyer as well, but you’re a seller in some ways. Logistic things, they go silent. You’re trying to reach them and they just don’t reply. It could be for very legitimate reasons. They’re overseas. They’ve had a fundraising round, whatever it is but it’s how to be super communicative, asking for feedback. This is one that shocks me how few leaders ask for feedback. The more senior you get, it’s hard to ask to have the mirror held up to you.

At the end of the day, the hundreds or thousands of people that work for you are all trying to tell you how great you are and how wonderful you are. The reality is, every single leader, when they’re going through a process like this, needs a truth-sayer. Somebody that will hold the mirror up to them. Ask for feedback. Ask for feedback after you’re done with the discussion. Ask for feedback from the recruiter who brought you in. Ask for feedback from the person you met with. Keep showing that mindset, that willingness to learn, and that curiosity. That’s important.

A couple that I will share with you that they’ve never repeated, so it will never happen again, I have to imagine. This is a leader from a while ago. When business cards were handed out, though, they’re not anymore, but this leader took the business card of who he was meeting and set his drink on top of the business card as a coaster. It didn’t go very well. Another one that was kind of unique was when you go into a conference room. There’s a moment where, unless you’re predetermined where you’re going to sit versus the person that’s interviewing, going to sit.

I don’t recommend as the interviewee that you take the head of the table. That’s definitely not recommended. However, people do it. Those subtle signs of etiquette, those subtle signs of consideration, all matter. All of this matters. It’s sometimes not just what people think, “I nailed the interview, but guess what? They were rude to the receptionist when they walked in,” or some other silly thing happened. Those are all things that could ruin a candidate.

This continues through into the offer process as well.

The Unseen Traps Of Executive Hiring

It does. The offer process. A couple of things that trip people up late in the process are one, negotiating. People who get too aggressive in negotiating. That can take lots of different forms, but sometimes there’s a confusion between what offer even means because there’s multiple uses of the term offer. There’s a framework of an offer, a verbal offer, a written offer, or a signable offer. They’re all very different. People get very confused when they throw the term, “I got an offer.” The only one that matters is you get a written offer and is it a signable offer. That’s the only thing that matters because you know your value.

At least for that company, your value. You have a data point. When they try and negotiate too aggressively because they think they have the opportunity in the bag, we’ve seen many opportunities where the company’s cut bait because what they’re viewing you as, and they’re watching you is, if this is the way this leader is going to show up to negotiate, is this how they’re going to show up internally or with our clients or customers? We’ve seen that happen more than a few times.

The other way is when they resign. We talk a lot about the resignation process in the book and lay out a step-by-step program to do it well. People that don’t do it well, they get counter offers. They accept counter offers, and they leave the company that gave them the offer high and dry. Jeff and I had a recent example of this where we were negotiating for a public company CEO role. The person had a written offer, was negotiating it, and said, “If we can get the compensation right, I’m going to take it.” We told that to the entire board. That was on a Friday or Thursday. That following Monday, that individual took another role in another company. Never told the company that they were negotiating with and literally just ghosted them. That is not the way to do it.

You have a lot of examples in the book. Don’t burn bridges.

For that same search I was just talking about, I’ll give you a perfect example about not burning bridges. A name came up to the search committee on this CEO search. Somebody on the search committee said, “I knew that individual twenty years ago, and that person was a jerk. We definitely are not going to consider that person.”

Think about that for a second. Somebody that knows where they were in their career acted like a jerk, had that reputation, burned that bridge. Twenty years later, that individual will not even know what is being said about him or her when they’re not in the room. Whether that person wanted the job or not, they’re not even getting the opportunities because that’s the reputation they built.

Kelly, thanks for doing this with me. I’m sure your book will be incredibly beneficial to anybody who’s in the job market and we all are at different points in our career. Getting these interactions with search firms like Heidrick is important for people. I’m sure this will be an episode that a lot of people will find very useful. Thank you for doing it with me and best of luck with the continued launching of your book.

I appreciate you having us on. I hope that your readers get a lot of value from it. Hopefully, it’s a value.

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Wrapping up the conversation just now with Kelly, let me offer a few takeaways. Most importantly, manage your career before you need to. Don’t wait until you’re miserable, unemployed, or desperate for change to understand your market value, build your network, establish relationships with recruiters, or think seriously about what you want next. Career management should be ongoing, not episodic. If you’re a regular reader to this show, this is something that I emphasize all the time and feel strongly about.

Second, know your story, but don’t turn it into a script. Your resume is going to tell people what you’ve done. Your job is to explain the context, the impact that you created, what you learned, and why that experience makes you the right person for this particular opportunity. A lot of people know that they’re supposed to tell stories in interviews, but if you just tell the same story again and again, and don’t link it to what that person in that seat who’s interviewing needs, then you’re missing an opportunity to connect with them and to show them that what they need and are the right person for that role.

Third, remember that you’re evaluating the company too. The objective isn’t just to get an offer for the sake of getting an offer. It’s to find a situation in which your strengths, aspirations, values and definition of success align with what an organization needs. Kelly talked about the importance of going into a discussion with a recruiter or a company with clarity on that. If you have that, then you’re going to be able to have a much more informed conversation about whether this situation that you’re talking about is right for you.

We build our careers one role at a time. Though we’re changing jobs more often than we used to, you don’t get an infinite number of career tries. You’ve only got a finite number of them. You want each one to count and be right for you, to contribute to your broader success, and to leave you feeling happy and fulfilled every day.

Finally, is just this idea of how you show up throughout the process matters incredibly. It is not just the interviews. Your phone conversations, how you respond to email or tone, or whether you put your drink down on somebody’s business card or sit in the seat at the head of the table. A couple of things that Kelly mentioned in the course of our conversation, all of that gives the company that you were interviewing with data.

You want that data to be good data. You don’t want it to work against you. Yet a lot of people self-sabotage intentionally if they’re trying to be too hard a negotiator or unintentionally by just doing something that rubs somebody wrong. I’ve certainly seen this in my own experience. It’s a great conversation, lots of practical advice, especially if you were in the job market, but the point is you were always somewhat in the job market.

If you found this conversation valuable, please subscribe, leave us a review, and share this episode with somebody who may be looking for a job or just wants to manage their career better. In other words, all of us. You can also sign up for my membership community, which is called PathWise and our newsletter PathWisdom. Thanks for tuning in.

Important Links

• Kelly Kay on LinkedIn
• Heidrick & Struggles
• Jeff Sanders
• Show Up to Win: How to Land the Leadership Role You Want
• OpenAI
• PathWisdom Newsletter
• PathWise on LinkedIn
• PathWise on X
• PathWise on Facebook
• PathWise on YouTube
• PathWise on Instagram

About Kelly Kay

Kelly O. Kay is a partner in Heidrick & Struggles’ San Francisco office and the global managing partner of the firm’s Enterprise Software and AI Practice. With 22 years in executive search, Kelly conducts searches worldwide for a wide range of technology companies, from high-growth private and public enterprises with revenues up to $100 billion. Kelly specializes in senior go-to-market leadership roles, including board, CEO, COO, CRO, and worldwide sales. He co-founded Heidrick’s Sales & Commercial Officers Practice and is a leading voice on executive talent trends in B2B software. Before executive search, Kelly was a partner at the Center for Corporate Innovation (CCI), a CEO development and strategy organization sponsored by McKinsey & Co., and earlier held senior roles at IBM Corporation and Gemini Management Consulting. A sought-after talent adviser and public speaker, Kelly’s writing has appeared in Harvard Business Review, Forbes, and The Wall Street Journal. His HBR article on resignation best practices “Leave Smart, Land Well” was based on a national survey of more than 6,000 CHROs and senior executives and became one of the publication’s most widely read pieces on executive career management. Kelly holds an MBA from the University of Southern California’s Marshall School of Business and a bachelor’s degree in Marketing from the University of San Francisco.