The Best Way to Learn From CEOs? Study Their Mistakes

 The Best Way to Learn From CEOs? Study Their Mistakes

Is studying great CEOs the best way to learn? It’s certainly valuable, but there’s more to be learned from CEO blunders. Here’s why.

Analyzing effective CEOs is limiting for two reasons. First, successful CEOs do so many things right that often it’s difficult to figure out what to imitate.

Second, people often focus on a CEO’s most idiosyncratic trait–such as Steve Jobs’s temper or Richard Branson’s flair. They conclude that this must be what made him effective. Many CEOs succeed despite their quirks, but people don’t see the full body of work that led to their achievements.

Instead, examining CEOs’ mistakes is a more fruitful endeavor. The nature of the CEO role makes it much easier to learn from failures than successes.

CEOs not only have to determine the strategic direction of the organization but also ensure that everyone is steadily making progress toward it. Even with that clear destination, there are many decisions CEOs must make along the way–and lots of room for error. Part of the CEO’s job is to peer into the future as far as possible and identify any issues that might impact the business. Then of course, they need to take corrective measures.

This is similar to a ship’s captain who is constantly looking into the fog to avoid obstacles. The basic sailing of the ship is fairly easy and well-understood. What makes the job challenging is the constantly changing weather conditions and currents.

When you assess a superior captain, it is hard to know what to home in on: Is it his lucky hat or years of experience that contribute to his success? The barriers he adroitly avoided or the disasters he averted may never come to light.

On the other hand, their failures are more revealing. It is simpler to examine a CEO who sailed his company straight into an iceberg and figure how to avoid that particular error.

This is similar to the CEO job. There is certainly ample material, in every industry, of CEOs who have failed along their journey due to personal issues, poor business decisions, criminal acts or other reasons. Just look at past CEO oustings such as J.Crew’s Mickey Drexler, Uber’s Travis Kalanick, Zenefits’ Parker Conrad, or Betterworks’ Kris Duggan.

There are also many lessons to be learned from more notorious or classic CEO debacles, including Jonathan Schwartz of Sun Microsystems (performance), Ken Lay of Enron (criminal activity), or Kay R. Whitmore of Eastman Kodak (failure to adapt to the market).

It is difficult to look at Jeff Bezos or Elon Musk and recreate what has made them successful. Studying the mistakes that other CEOs have made is the best way to avoid repeating their errors. It will also help you be a better leader.

First appeared on

Joel Trammell

Joel Trammell is the cofounder and architect of CEO-S, an operating system for the chief executive. Joel is a previous CEO of private and public companies and the owner of Texas CEO Magazine. He is the author of The CEO Tightrope and, most recently, The Chief Executive Operating System (with Sherif Sakr).

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