An experienced CEO was offered the top role at a well-known public company with strong perceived fundamentals. He was excited to say yes. He’d met with all the board members, several of whom he knew personally. He had years of relevant industry experience and was energized by the role’s prestige and how it would build on his skillset and previous successes while offering new challenges.

But only a few months into the job, he discovered that the company had little room to maneuver in the face of unexpected headwinds and lack of flexibility due to financial pressures. “It was like being asked to run a six-minute mile — from a quarter mile behind the starting line,” he reflected later. “I didn’t have an accurate view of where we were actually beginning.”

Overnight, it became clear that the trust he placed in board relationships meant he hadn’t been as rigorous as he should have been during his pre-decision analysis. He also made assumptions about the top-tier board and well-known founders that left him unprepared for the ensuing turmoil.

Within 18 months, the role had become the toughest leadership challenge of his career. An immense workload, significant stress, and a shareholder-applauded merger that nevertheless resulted in poor stock performance all branded his tenure as less than stellar. His reputation took a hit, his family endured the stress of a high-profile failure, and his next career options were limited. The company lost time, momentum, and credibility in the market.

In the end, he was a serial growth CEO charged to lead a turnaround — not his expertise or even what the company most needed, all with complex board dynamics he didn’t anticipate. The dream job became a nightmare.

Why This Matters

This story is not unique. In our work helping boards and private equity firms find, assess, and develop CEOs, we’ve seen this pattern repeat itself: Talented executives accepting roles that prove to be mismatches, leading to costly failures for both the individual and the organization.

CEO selection is not a one-sided act. It is a shared commitment to clarity, forthrightness, and aligned vision. Both boards and executives must agree on the blueprint — because they’ll both live with the results. According to a proprietary Spencer Stuart analysis, companies whose CEOs resign under pressure or leave within two years experience a 20% negative total shareholder return impact measured 24 months after the transition.

But here’s what’s often overlooked: Executives, especially top talent with many options, are not passive recipients of offers. They must interrogate context and challenge assumptions to determine whether a role is truly right for them. This includes making sure both conditions for success and conditions for satisfaction are understood clearly — and likely to be met.

This is an excerpt from The Questions CEO Candidates Need to Ask, which was published in Harvard Business Review online January 12, 2026.