Why I Spend My Time on CEOs

People sometimes ask me why, after running companies for most of my career, I've chosen to spend this chapter of my life working on the CEO role itself. Why not retire to the board circuit, write the occasional check, and offer advice when asked?

It's a good question, and it comes down to two primary reasons.

Frustration

The first is simple frustration. Over four decades in business, I have seen, more times than I care to count, companies with everything going for them fail because of poor leadership from the CEO seat. These businesses had a real market, a product customers wanted, talented people who showed up ready to do great work—i.e., everything you need for a home run. But then the ball gets chopped into the infield for a single. Or worse, the company strikes out entirely. Everyone involved is left scratching their head: How did we mess up such a sure thing?

With all the other pieces there, the answer is usually: the CEO. What makes it frustrating to watch is that the CEOs who preside over these misses are usually extremely smart and accomplished. They have a track record of achievement. They excelled at everything they did before becoming CEO.

But there was a problem. The CEO job is different from “everything they did before.” Nobody trained them for this role. They came to work on Day 1 not realizing they didn’t know the rules of the game they would be asked to win. They didn’t know how the pieces moved. They had not built the skills.

So they improvise. And the CEO job—a tightrope walk, as I describe it—does not reward improvisation. The cost of failed improvisation isn't borne by the CEO alone. Employees’ careers are affected when the company stalls out or goes under. Customers don’t get what they wanted. Investors and shareholders who backed the vision are left holding the bag. Thus, when a CEO fails, the failure cascades through hundreds or thousands of lives. Not to mention, such losses are huge sources of squandered value in the economy.

So one reason I am driven to help CEOs understand the job and do it well is that it’s really hard to watch preventable mistakes. And they are preventable. Every good sales executive, HR leader, CFO, etc. has a clear system and tools for delivering results. Such a system and tools are available to the CEO too. The problem is one of information sharing and good training. That is the gap I aim to fill when I write books on the role, teach classes on it, and develop tools for CEOs.

With a real operating system, the opposite of the needless strikeout can happen, too. I have also seen companies that should have been modest successes turn it into something remarkable. I’m highly motivated by my desire to see more of that kind of winning rather than strikeouts that should have been home runs.

What I Hope to Leave Behind

The second reason I spend my time working with CEOs is more personal. It took me longer to figure out how to articulate.

At a certain point in life you start thinking about what you'll leave behind. Will your professional legacy be a monument to the past? A company you grew decades ago? Your name on a building? I decided I don’t primarily want to be remembered for that kind of thing. I’d much prefer to be remembered for something I offered that’s helping people now.

That is a demanding standard, because it means the work can’t be frozen at a certain point in time. It has to stay alive. I find myself asking what I can do now to help others in their own future. If I can guide a first-time CEO through her first board meeting this quarter, or help a stagnated CEO see his blind spot that has cost him two great executives this year, that is success to me. By that definition, legacy is about whether you are still useful right now, to people navigating the highest-pressure job in business today.

This is why I keep writing, keep teaching, and keep building tools for the role. Not because the world needs another retrospective from a former CEO, but because there are 200,000 sitting CEOs who got handed the most consequential job in their company with no manual and no support system. Every one of them is one bad quarter away from becoming another cautionary tale about wasted potential. I want to be their first call when they have an issue.

If I can help a CEO run their company a little better because of something we worked on together, that's the only kind of legacy I'm interested in anymore.