The Most Useful CEO Assignment Is Writing Your Own Retirement Speech

In The Wall Street Journal, Callum Borchers looks at a trend that surprised me less than it surprised him. In Why CEOs Go Back to School After Making It to the Top, he reports that executive education programs are flourishing as leaders confront an AI landscape they never studied, along with hard questions about what ethical, human-centered leadership should look like.

The details are telling. Some programs ask participants to sign nondisclosure agreements so executives can speak freely. Former Harvard Business School dean Nitin Nohria told Borchers that only one in four leaders invited to the school's New CEO Workshop accept, and that those who come often feel overwhelmed. New CEOs, he said, arrive thinking they were "master of the universe" and find they don't feel that way at all. One of the first assignments is to write their retirement speech.

Borchers presents this as a story about learning and camaraderie. I read it as a story about identity, and about what happens when a leader reaches the top of the ladder and finds the title doesn't answer the question they thought it would.

The Title Arrives Before the Clarity Does

Most executives spend decades earning the next promotion. Each step comes with a clear target and a clear scorecard. Then they reach the role with no step above it, and the scorecard changes overnight. Results still matter, but now the whole organization is watching how they think, what they tolerate and who they become under pressure.

That is a disorienting moment, and the article captures it honestly. Several executives described a precarity their predecessors didn't face: employees who are more likely to criticize them online than flatter them, and private remarks that can leak in an instant. The confidence that came with the climb doesn't automatically transfer to the summit, because much of it was borrowed from the next promotion. At the top there is no next promotion to borrow from.

I've seen this pattern in my own work with leaders. The ones who struggle most in their first year aren't the least capable. They are the ones whose sense of self was built almost entirely on advancing. I wrote about what that looks like from the inside in Success Theater Is a Culture, Not a Surprise.

Why the Retirement Speech Works

Of everything in the article, the retirement speech exercise is the part I'd most want every leader to try, at any level. Borrowing a line from the piece, it is something anyone could do, though it sometimes takes the structure of a classroom to make us do it.

The exercise works because it reverses the order most careers follow. Instead of asking what you need to achieve next, it asks what you want to have stood for when you're done. That question can't be answered with a title or a stock price. It forces a leader to name their values, the problems they want to be known for solving, and the kind of people they hope to leave behind.

This is reinvention at its most practical. Reinvention isn't about becoming someone new. It is about reclaiming what matters most to you and building forward from it. A leader who has written that speech has a reference point for every hard decision that follows, especially the ones where the right call and the popular call point in different directions.

Timing matters here. Teams form their judgment of a new leader quickly, often long before the board does, a pattern I described in By Month Six, the Room Already Knows. A leader who has done the reflective work early walks into those first months with something steadier than a plan.

Learning That Sets the Culture

One more point in the article deserves attention. A program director at Texas A&M told Borchers that when CEOs are deeply engaged in learning, they create cultures of learning. I agree, with one condition. The learning has to show.

A weekend program can give a leader frameworks, peers and perspective, and that consistency of preparation has real value. But a team doesn't learn from the certificate. It learns from watching a leader say what they don't yet know, ask better questions and change their mind when the evidence calls for it.

A few questions for leaders this week:

If you wrote your retirement speech today, what would it say you stood for? Would the people who work for you recognize it?

Where are you still leading from the confidence of the climb rather than the conviction of your own values?

What is one thing you are learning right now that your team could watch you learn, openly and imperfectly?

The executives in this story went back to school to keep up with AI. Many of them found they needed something else first: a clearer sense of who they are when the job no longer tells them.

The title tells people where you sit, but only the leader you choose to be tells them where you're taking them.

Want to explore these ideas further? Learn more about my work on leadership, identity and conviction at www.theglennllopis.com.