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The CEO’s Toughest Leadership Challenge—Leading Themselves

June 23, 2019, 1:00 PM UTC
Ron Williams speaks at BET's META conference on June 20, 2019, in Los Angeles.
LOS ANGELES, CALIFORNIA - JUNE 20: Businessman Ron Williams attends META Convened by BET at Milk Studios on June 20, 2019 in Los Angeles, California. (Photo by Bennett Raglin/Getty Images for BET)
Bennett Raglin—Getty Images for BET

Being a CEO is a daunting task. The challenge of leading a large, complex organization takes a range of talents that aspiring executives spend decades developing. Yet ironically, some of the most startling corporate missteps are caused by a much more basic failure—the failure of CEOs to lead themselves.

CEOs, especially in public companies, are in an unusual position. They don’t have a day-to-day boss providing input, feedback, and direction. They do have their board of directors, but the board members don’t participate in staff meetings, one-on-ones, or day-long operating review sessions—nor should they. And so they are unable to give feedback on the CEO’s behavior or on the results of those meetings.

Having a separate chairman, as opposed to allowing the CEO to serve as board chair, doesn’t solve the problem. The CEO must still spend all their time focused on the issues vital to the company’s long-term success, leaving precious little time for self-examination.

As a result, learning to lead yourself through self-examination is a skill that the CEO must constantly hone.

CEOs who have forgotten how to lead themselves are generally easy to find. Some end up in the news for unfortunate personal behavior. In other cases, their organization goes astray, or an unusual number of executive departures begin to crop up. These are symptoms of a CEO who has failed to realize the need to engage in deliberate, continual self-examination, developing and responding to the kind of objective evaluation of one’s own effectiveness and judgment that a CEO otherwise may never experience.

Over time, I developed some ways to maintain my personal focus on leading myself. Here are two examples.

First, I made a point of soliciting input in one-on-one sessions as well as requesting external input from trusted colleagues and professionals from outside the company on what I could do better and what I should stop doing. I also practiced what I call the two-down approach, meeting with people two levels down in the organization to get a better sense for what’s going on. (Before becoming CEO, I had also practiced the two-up approach, meeting with people one level above my boss, so I could better understand the vision and strategic direction of the company.) The two-up, two-down approach is a good way for any business leader to broaden their awareness of how they fit into the organization, revealing opportunities to improve the ways they are using their time, talents, and other resources.

Second, I worked to consistently focus on my personal and business goal of becoming 15% better every year. I found this to be a powerful development tool for me. The key is making yourself a promise to stretch yourself, and to grow and learn each year. You pick the number; then the challenge is to make sure you achieve it.

If you’re fortunate enough to be asked to fill the role of the CEO, you may experience a momentary sense of relief from the thought that you will never again have a boss looking over your shoulder, demanding the best of you.

Shake it off! The reality is that if you hope to succeed as CEO, you’ll need to begin reporting to a leader who will set even higher standards for personal achievement—yourself.

Ron Williams is the chairman and CEO of RW2 Enterprises, former chairman and CEO of Aetna, and author of Learning to Lead: The Journey to Leading Yourself, Leading Others, and Leading an Organization.

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