The CEO Who Has All the Answers Is Probably Asking the Wrong Questions

At 22, I thought I had the world figured out. I had graduated at the top of my class and regularly wrote crime stories that landed on the front page of a metropolitan daily newspaper.

Then the editor invited me into his office. “Tim,” he said, “you have all the talent in the world, and you are going to go places. I know it. But you can’t write worth a shit.”

There are moments when all the air leaves your body. This was one.

He opened a folder containing several of my articles. He had rewritten each one to show me how they could have been better. And he was right. I left his office on my way to becoming a better writer and ultimately his replacement as editor. More importantly, I had encountered a leader willing to invest time in someone who hadn’t yet earned much of it.

Decades later, after running newspapers, owning a small business, and coaching business owners, I think about that editor whenever I encounter a CEO who believes leadership means having the answer to every question. That’s wrong. Leadership is preparing the next generation to answer those questions.

Why we have trouble letting go

The temptation is understandable. A CEO has experience. People bring problems. The CEO solves them. Everyone moves on. It feels efficient. The CEO also feels good because she is needed.

I worked with a family business where the founder announced he was retiring and turning the company over to his son. Except he didn’t retire. He continued showing up, talking to customers and involving himself in decisions. Meanwhile, his son was trying to straighten out years of financial problems and damaged relationships.

The father had given up his title but not his authority.

I don’t think he was deliberately trying to undermine his son. The business had been his life. For decades, he was the person everyone depended upon. Now he was supposed to sit on the sidelines while someone else made decisions, including some he did not understand.

That’s difficult for a lot of CEOs. We worry that someone else will make a costly mistake. We believe our experience gives us better judgment. And, if we’re willing to admit it, we enjoy being the person everyone needs.

Sometimes the biggest obstacle to a company’s future is the person who built it.

When I knew everything

I wish I could tell you I always practiced what I’m preaching. I didn’t.

Years ago, we were moving our newspaper’s administrative offices from an old, drafty building into a brand-new facility. I saw an opportunity to create a workplace for the future, one that encouraged collaboration instead of isolating people behind closed doors.

I wanted desks on wheels that could be pushed together for meetings. More radically, I wanted department heads working in the open alongside their employees, with small “huddle rooms” available for private conversations.

I had seen something similar at Procter & Gamble’s headquarters in Cincinnati and was convinced it was the future.

My department heads hated it. My wife hated it. The managers even started calling the huddle rooms “cuddle rooms.”

I didn’t listen.

A few months later, I left the company for reasons unrelated to the office design. I subsequently learned that the department heads had immediately abandoned the arrangement and returned to traditional offices.

Perhaps my idea was ahead of its time. Perhaps it was simply a bad idea. Either way, I had failed to listen to the people who would have to live with my decision.

I wanted a workplace that encouraged collaboration. I had designed it without collaborating.

Tend the garden

When I became an editor, I worked with colleagues who believed the boss should approve every headline and paragraph before the newspaper went to press. I disagreed.

I wanted reporters and editors to make decisions. If they made a poor one, we’d talk afterward about how they reached their conclusion. What information did they have? What alternatives did they consider? What might they do differently next time?

Sometimes I disagreed with their judgment. Sometimes they had seen something I missed.

My job wasn’t simply to produce today’s newspaper. It was to develop people who would make better decisions on tomorrow’s newspaper.

I came to see leadership as tending a garden. You select good people, create conditions in which they can grow, offer feedback and remove obstacles. You can’t do their growing for them.

The paradox is that the better you become at this job, the less indispensable you become.

Some CEOs find that threatening. They shouldn’t. When good decisions are being made without you in the room, that’s evidence the organization is getting stronger.

Knowing when to step in

Of course, there’s a difference between developing people’s judgment and leaving them to figure everything out for themselves.

I think CEOs have three choices when someone brings them a problem.

Coach when someone needs to develop judgment. Instead of providing the answer, ask what they think is happening. What alternatives have they considered? What would they recommend? Then listen. Don’t ask questions while mentally preparing the answer you intend to give anyway.

Delegate when someone has demonstrated good judgment. Give them authority along with responsibility. Make clear what decisions they can make without you and when you expect to be consulted. If you insist on approving every detail, you haven’t delegated anything. You’ve just assigned someone the task of carrying out your decisions.

Intervene when the stakes demand it. Legal, ethical, safety or serious financial consequences sometimes require the CEO to step in. But even then, intervention doesn’t always mean taking over. Sometimes it means helping someone think through a decision before the organization suffers the consequences.

The difficult part is recognizing which situation you’re facing.

A five-minute answer might solve today’s problem. A 20-minute conversation might help someone solve the next dozen without you.

That seems like a pretty good investment.

The real return

The 22-year-old me learned something else from my editor that day. He genuinely assessed my writing and then showed me how to make it better.

That’s what coaching requires. Honesty, patience and a willingness to invest in someone else’s success.

A company that depends on the CEO for every consequential decision is fragile, no matter how talented that CEO may be. The stronger organization has people who can assess problems, challenge assumptions and make sound decisions themselves.

Your job isn’t to be the answer to every question.

It’s to build a company that knows how to think.