Your Next Executive Career Move Is a Judgment Test

Kelly O. Kay was working a CEO search for a big-brand public company when a name came up.

The chairman of the nominating and governance committee didn't ask for a résumé or a reference.

He said, "Nope, wouldn't want to engage that person. I knew that person 20 years ago, and that person was a jerk."

That was the review. Your next executive career move gets scored the same way: by people reading evidence you created years ago, in rooms you will never see.

We spend our energy on the part of a move we can see, the title, the comp, the announcement. Kelly has spent two decades on the other side of the table, and the deciding evidence he describes sits somewhere else.

Kelly co-wrote Show Up to Win: How to Land the Leadership Role You Want with his Heidrick & Struggles colleague Jeff Sanders. Our conversation on Finding Peak kept coming back to one question: what are the people hiring you scoring?

The title is the part people can see

Kelly has six kids, five of them in the work world, and he gives every one of them the same advice: never chase money. "If you're good at what you do, money will find you." For executives he adds a second rule. Never chase a title.

The title warning is the one that stings. Say you want to be a CEO. "And guess what? You will be a CEO," Kelly said. "But it's of a company that you're not going to want to be a CEO of." Without the background to land at a high-quality company, he said, you spend two or three years of your life on something that may not amount to much. His alternative is boring and correct. Assess companies on quality rather than the title, and stay in a role long enough to have achieved something.

He can also tell when the ambition is borrowed. Plenty of executives tell him they want to be a CEO, Kelly said, and when he looks them in the eye, their eyes shift up and to the right. They're saying it because a spouse expects it, or their network does, or because they're talking to a recruiter and think it's the right answer.

Then he named a pattern I recognized in myself. Leaders are competitive. They enter a hiring process and start trying to win it, in his words "almost irregardless of what their interest is." Often, he said, he gets to the end of a process, tells the candidate an offer is coming, and asks whether they want the job. "And you're like, I don't know. It happens all the time."

Winning the process is not the same as wanting the job. The title is the scoreboard you can read from the stands. The people deciding on you watch other numbers: what you finished, how you got there, and whether your choices make sense. As I put it to Kelly, being hired on potential works for maybe one or two jumps. After that, someone asks what you did.

How you got there is the part a résumé can't show. Kelly's phrase for it is "relationships are currency." The best thing anyone can do for him, he said, is "say something nice about me when I'm not in the room. That currency is more valuable than my paycheck." That chairman was spending the same currency in the other direction.

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I won the title and hated every second of it

I know this one from the inside. About ten years ago my ego talked me into a job for the title and the money. The company gave me both. None of what followed was their fault. It was the wrong fit, I hated every second of it, and I was gone in nine months. I later turned the lesson into a TEDx talk, Stop Living a Life You Didn't Choose.

The talk was about what that job cost me. Kelly went straight to what it costs on paper. After a bad move, he said, the question everybody on the hiring side asks is about your judgment. "They question your judgment. That's what they question."

The instinct is to hide the short stint. Kelly's advice runs the other way. "Everybody will give you a hall pass," he said, but you have to call it out: what did I miss when I took the role, and why won't I make that mistake again? "We all make mistakes with our career. All of us do... Just make sure that you know why you made it."

That reframed my nine months. A bad move won't end a career. An unexplained one raises the same question in every room you walk into. Ten years later, I can say it plainly: I made that decision for the wrong reasons, and it taught me how I choose where to work. Once I could say that out loud, the nine months turned into a story about judgment instead of a hole in the résumé.

Take the call before you need it

Kelly splits this work into two jobs, career management and career transition. Transition is the move itself. Management is everything you do while you're happy, and it's the part that gets skipped. If your head has been down for years and you've met nobody outside your company or industry, he said, you start from scratch the moment you want to move.

Career management starts with the recruiter call you don't need. You like your job. The phone rings anyway. Take it, Kelly said, because if you haven't been to market in a while you can't answer three questions: "How attractive are you in this market? How valuable are you in this market?" And what is your narrative for the things you've accomplished?

Someone once brought me this exact question. They liked their job, had no real problems, and got an offer to have a conversation. Saying yes felt like cheating on their company. Kelly didn't hesitate. "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."

He added guardrails. Be careful with a direct competitor. Don't get seen walking into another company's office. And keep the conversation in proportion: "just because you say yes to a conversation, nobody's offering you a job."

The way I'd put it: the call is market research. You can't price yourself if you never check the market, and as Kelly said, you build those relationships when you don't need them. Building a network the week you get fired is buying insurance after the fire.

Walk in with their problem, not your trophies

I asked Kelly a question I've lived with for years. I have a podcast and a public body of work, and I wanted to know how a personal brand plays in a search. His answer was blunt. Leaders walk in and talk about their brand and what they've done, "and no disrespect, but really nobody cares. Because the only thing they care about is, can you solve my problem?"

In Kelly's view, the time a senior hire gets to make an impact has gone from years to months to weeks. Companies don't have time to teach you what they want. So do your homework before the meeting. Ask what they're solving for with this hire, what the issues were, and what they've tried. Then bring examples from your own career that show how you'd think about their problem. "Nobody's hiring you for what you did at whatever company before," he said. "They're hiring you for this company to solve this problem."

His best line was about questions. "You can show me how you think by the questions you ask versus you telling me what you think." He doesn't mean interrogating them for an hour. At some point, he said, you have to put a point of view on the table. The goal is for the person across from you to "visualize you in that role in that company."

I put it to Kelly this way. It's easy to sit down, point at the awards behind you, and watch the other person think, so what?

Then the coach. A couple of months ago, an executive about to become a CRO for the first time called Kelly. Kelly asked whether he'd asked for a coach as part of his negotiation. No, the executive said, they would think I'm weak. Kelly laughed. They know you haven't been a CRO. They've seen your résumé. Asking for a coach tells them you know where the gap is, and the company wants to protect its investment from rookie mistakes. Kelly called it "a vulnerability that is a sign of strength."

Run the judgment test before your next executive career move

The filter I'm keeping from this conversation is four questions. Answer them before you take the call, sign the offer, or update the headline.

Did I achieve what I came here to do, or am I leaving on potential?
Would I still want this company if the title were one level lower?
Can I explain this move in two sentences to a board five years from now, including what I might get wrong?
What will people say about how I got here when I'm not in the room?

A shaky answer on one of them doesn't kill the move. Shaky answers on all four usually mean you're chasing a title.

My nine-month job fails the second question. Fit is the deeper version of it. It took me a long time to realize I'm a wartime general. Put me in an established company where 3% growth is a great year and I'm the wrong executive, whatever the title says. That fit question, finding the work where your natural edge creates disproportionate value, is the heart of the book I'm writing. Get on the Easy Mode waiting list for book resources and updates: https://ryanhanley.com/easy-mode

Somebody in a room you'll never see is going to say your name. Give them something worth repeating.

Listen to my full conversation with Kelly O. Kay: https://linktr.ee/ryan_hanley

Watch it on YouTube: https://youtube.com/ryanmhanley