How A CEO Knows It’s Time To Go

When does a CEO know it’s time to leave? Well, one way is when the board shows you the door.

But somewhere short of that, when does a CEO know it’s time to leave even when you’re still enjoying a good run?

If you’re the CEO, no one but you can answer this question. But we can provide you with some clues about what to consider. It may be time to leave if…

  • You’re not having fun anymore. Deep down you’ve been sensing this fuzzy feeling: same ol’ same ol’. You find yourself sighing before, or worse, during, meetings that used to light your fire. Your mind drifts to golf or getaways or something, anything, much more often than ever before. Leadership’s a drag and you just haven’t admitted it to anyone but your dog.
  • You’ve accomplished all the organizational goals you set out to achieve. Life’s good. You and your team got it done. Maybe you’ve even won accolades and awards. But what now?
  • You can’t envision what the organization looks like or where it’ll be in five years. Early in your career “the vision thing” was a snap, but now you struggle to see around the corner.
  • You’re finding it more difficult to make the hard decisions. Fire someone? O.K., if you considered it legitimate and something the organization needed, you got it done. Now, pulling the trigger causes you more stress than the departing employee. Closing a program, product line, or service? Way more late-night anxiety than it used to be.
  • You respond with “I fixed that five years ago” when personnel come in with a new idea. After awhile, the Innovator-in-Chief can become the chief obstacle to innovation. You’ve been-there-done-that and you don’t want to do it again, even when marketplace gurus say “change” is the name of the game in the-world-is-flat economy.
  • Your skills no longer match the organization’s challenges or opportunities. You came as a builder, you built, and now what do you do? Or you’re a finance wizard who re-engineered the organization and made it profitable again, but now the organization’s challenge requires a marketer or visionary or technocrat. The organization needs new blood and you no longer have the right blood type.
  • You’ve got the itch to do something new. You’ve always wanted to go out on your own. Risky? Yes, but oh, bring it on. You’ve counted your years until age 65 and you want to spend them doing what matters most to you. You’ve accumulated assets. Now you want to accumulate experiences, or better yet, you want to give back time, talent, and treasure. You want to serve.
  • You sense you’ve allowed yourself or others to slip into that dangerous zone where you or they confuse your identity with the organization. Founders are especially susceptible to this pitfall, but any long-time leader can fall victim to reading his or her own press. The danger for the organization is that the emperor may have no clothes and no one can or will share the bad news. The danger for the leader is a potentially very difficult emotional adjustment when the break finally occurs. Less adoration, fewer perks, no power. You forgot that the organization is not about you.
  • You and/or the organization are under serious political or financial pressure. No one can be a CEO without pressure. Nothing new here. But now the pressure is at a level it’s never been before. Or the pressure is coming from sources formerly unwavering in support. Or the pressure is more about you, your vision or style, than it is the organization’s challenges. How serious must the pressure be for the CEO to know it’s time to leave? It all depends. But when you’re shaving or putting on your morning make-up, look yourself in eye and evaluate the question honestly. The organization may be better off without you.
  • You’re guilty of some kind of professional ethics violation and you know it. Too many high profile corporate and governmental scandals have occurred in the past decade to ignore the unfortunate possibility of this one. If the shoe fits, wear it, own it, change it, but don’t keep running from it. Prison is not a nice retirement community.
  • You’re tired, physically, emotionally, mentally, maybe spiritually. It’s no shame to be tired. When he announced his retirement, even Green Bay Packers superstar quarterback Brett Favre said “I’m just tired mentally.” Tired doesn’t mean you’re old. It means you’ve given your all and you need refreshment.
  • Your spouse or family or friends want more of you. A lot of leaders announce they’re moving on to “spend more time with my family,” but this is often a convenient euphemism for “I’m getting out before they throw me out.” This said, family and friend considerations are real and worthy. It’s an old saw but one with power: “No one chooses an epitaph that says, ‘I wish I’d spent more time at the office.'” Organizational leadership comes and goes, friends last a lifetime, families are forever.

Unlike political leaders, corporate and nonprofit CEOs don’t typically work with term limits. When they leave is either their board’s decision or their own. CEOs by definition don’t have a lot of people telling them what to do. So the capacity to recognize the clues that it might be time, and to consider them honestly with mentors and confidants, is a huge asset.

CEOs who stay too long are probably more common than CEOs who go before their time. We are creatures of habit. We like our house and the community. We have adult children and grandchildren nearby. We find it harder to make a change because the mirror says we’re getting older. It’s not sinister. It’s human.

Yet, CEOs who overstay their effectiveness or their excitement are doing no one a favor, least of all themselves. Our egos and our insecurities tend to make us forget that leadership is a temporary stewardship. It always comes to an end. The trick is to bring it to an end when it’s in everyone’s best interest.

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