What CEOs regret the most

Regret has surfaced in my conversations with dozens of CEOs, often unprompted.

Most often, the regret is about a decision. I assumed that meant all sorts of decisions, from strategy to program to capital investments.

But when I dug in a bit, I found something else.

CEOs are four times more likely to regret going too slow than going too fast.

Jonathan Reckford has led Habitat for Humanity International since 2005. In our conversation for an upcoming episode, he put it as a career-long audit of himself:

In looking back at my career, I can't think of a time—any time—where I acted too soon to move somebody out of a role they weren't suited for.

Nearly all of the decisions CEOs wish were made faster were about confronting or removing an employee. The ones they wish they had slowed down were generally about strategy, almost never about a person.

One CEO named the pattern before he named his own part in it:

We often don't move quickly enough to move on staff who aren't working...Some of the worst decisions I've made are not moving on people who I wasn't sure about. And what I found when I finally did, is that staff had really suffered. And you just don't know it. So there's a massive opportunity cost.

Compare that to the regrets that run the other way, where a CEO decided and moved too quickly. These tend to be about strategy or program, technical or conceptual moves, rather than emotional or personal.

In Episode 10, Peter Greer, who leads HOPE International, apologized to his global staff for pushing growth too hard:

The biggest champion of growth was me...I led the organization in a way that directly led to some compromises in systems, and didn't pay attention to the cracks.

I haven’t yet found a CEO who felt the need to apologize to their staff for having moved too quickly to move out someone who is a bad fit, underperforming, or toxic.

Delayed personnel moves are a fountain of regret.

Will Jones leads Thompson, a child and family services organization in North Carolina. In an upcoming episode, he put a number on his own delay:

I tend to allow people a lot of space to decide if they want to learn and grow, and help them with that. I probably wait too long. And quite frankly, I think we probably could have [grown dramatically faster] if I would have acted faster.

Another CEO put it crisply: "The ones that I regret are the ones we didn't pull the trigger on when we knew."

The rationale for the delay in these personnel situations is a desire to be kind. (You may remember this theme in my article The Niceness Trap earlier this year.)

Reckford again, in the same breath as the audit above:

We want to be kind, which is good. But it's not kind to leave somebody underperforming in a role. It's not kind to them, and it's certainly not good for your mission. From a missional perspective, ducking those decisions means that you're essentially saying personal comfort is more important than my mission.

Oof. 

Others said the same thing without the frame:

• "It comes from a good place."
• "Holding on to people too long, before just going, oh, you're done, because I was too nice."
• "We all want to be nice people. I didn't fire them when I should have. Cost a lot of money."
• "I have tended to rely more heavily on grace, and just maybe, if I keep working at it, it will solve it."
• “It comes back to my tendency of wanting to be liked and not making hard decisions.”

CEOs are seven times more likely to point to kindness as the reason for the delay, rather than to the need for more information. 

There are occasions when CEOs need to slow down. A couple CEOs have even made the case to me for deliberate slowness, like Johnstone Ndunde of SIL Global, in an upcoming episode:

Sometimes you know the right decision to be made, but what is the consequences of making that decision?...You'd rather hold on that decision and wait for a while, and allow for the ingredients that make that decision to be right to be evident.

I think that’s true. But that it is usually about A) strategy, or B) organizational complexity. SIL is a huge, complex, global organization with thousands of employees. There are substantial linguistic, cultural, legal, and programmatic dynamics to navigate. That is a different category than the decisions CEOs tell me they regret delaying.

So what should you do when vexed by a decision? How do you get unstuck, break past the delay, to begin making progress again? 

Dig down to the root. (No, the real root.)

If you don't feel like you have good counsel from your board or others around you...it just took me way too long to decide things, because I was too full of self-doubts.

That CEO was running a small organization. Without quality counsel, the self-doubt wins. You are paralyzed. It’s imperative to be brutally honest with yourself about your reticence to decide.

Someone outside the situation is a gamechanger.

That's been good for me, too, to talk to somebody. And they say, "Dude, you've got to fix this." And I say, "But I'm trying to give him a chance, he's a good guy." And they're like, "You've got to knock this off."

Another CEO had a friend who kept asking him the same question:

"What's stopping you from making that decision? You're the CEO!" 

"Nothing's really stopping me, other than my own fear of rocking the boat."

You must admit what the delay costs everyone else.

One CEO called herself a slower decision-maker, by temperament. She began noticing what deliberation can cost others on the team:

We've had…problems that I have let go on for a long time, until I realized how my staff was suffering [as a result]. Okay, I’m done with that.

That is the same discovery the CEO at the top of this piece made, but too late. He found that "staff had really suffered, and you just don't know it."

To a person, these CEOs are smart leaders. They are compelling. Their organizations are stable, doing vital work. 

They just needed to see who was most injured by their waiting. 

We all like to be liked, but some of us much more than the rest. Many CEOs are accustomed to high degrees of warmth and kindness, the very impediments to making hard personnel moves as soon as you know you have to. 

The delay dissolves when you can say it out loud to someone who has nothing riding on your answer. And it ossifies when you carry it in isolation.

Good leaders make others sit and suffer—sometimes for years—because they can’t talk to anybody about it. 

Kaitlyn Slate, who leads Growing Hope Globally, named it plainly in this week's episode: "It is the loneliest position I've ever been in. There's so much that I can't share...but others in the position can uniquely understand that."

So, I have an exhortation for you for the coming week…

There is probably a decision you have not made. You have delayed and stalled in the name of thinking and analysis. But that’s not what is needed. 

It needs a conversation with someone outside your system. Someone with nothing riding on your answer. Someone who has seen this before and can describe the terrain to you 

Sadly, most CEOs cannot name that person.

What's stopping you? You're the CEO.

Adam Jeske, The Nonprofit CEO Advisor

P.S. You should listen to the full conversation with Kaitlyn Slate of Growing Hope Globally here, because she is a smart, humble leader doing vital work. 

I'm writing Peerless: Nonprofit CEOs and the Decisions They Carry Alone. You probably have a story of a decision that you delayed longer than you should have.

Please reply and tell me about it. This me helps me build up CEOs throughout the sector. Thank you.