When Is It OK to Fail As a CEO?

Twice in my career I quit high-paying jobs (one a CEO slot and one running a 7,000-person division) because I had unethical or wrongheaded people to report to. Although this certainly cost me a great deal of money, I don’t regret either decision.

As a CEO coach, I’ve run into many successful leaders who’ve either quit or been fired from large jobs before succeeding in another. There are some situations where you cannot win, or more accurately where you cannot be principled and keep your job.

My warning is for those whose board or boss is asking them to compromise their values (or in extreme cases even break the law). You feel stuck because you make a lot of money, or have many stock options, or don’t want to lose face—so you start compromising on the big stuff. It’s a mistake! Your values, reputation, and sanity are worth more than your current job!

Reaching the C-suite requires compromise. You can’t, and shouldn’t, win all disagreements. Rigid thinking isn’t a hallmark of successful leaders. However, when and where you compromise is a series of important decisions. (I’m addressing senior leaders here, but this concept applies to everyone!)

Trading your soul for a pile of money or a big title will leave you a shell of a human. I’ve met too many wealthy, miserable people.

The problem often starts before you take the big seat. If you don’t take the time and make the effort to clearly understand your relationship with the board (or whomever you report to), you start the slip-and-slide process. If you don’t push back professionally when asked to do things that are counter to your values, the company strategy, or the ethical treatment of your customers and employees, you’re slipping and sliding into a dark hole.

I’ve had clients who are unwilling to reasonably push back on their board or boss, and universally they’ve suffered. I’ve also helped clients create reasonable arguments for why they couldn’t or wouldn’t do something unreasonable. In most cases, they prevailed. Don’t sweat the small stuff, but think hard about the big stuff.

Getting to mahogany row doesn’t imply job security. Sometimes you have an obligation to yourself, your family, your employees, or your shareholders to say no or even quit. That isn’t failure, but rather an inflection point, perhaps even a wonderful opportunity.

Write down what the big “win” is for you. I doubt it’ll involve giving up your values, your self-esteem, your reputation, perhaps even your family for a bigger title or more money. Yet when you put one foot on the slippery slope, it’s hard to recover. Take the long view!

Please share
Follow Me