"The Decisions That Keep You Awake at Night." This is the Job of Leaders.

[Note: This article was published as part of our original "Leadership Moments" series. The series has since been changed to "Leading in the B-Suite" for a new focus on conversations about race in corporate America. The first interview in that series is here.]

If they're not careful, leaders can find themselves making dozens of decisions every day, rather than pushing the responsibility down to the people who should be making them. A key test for delegating is whether the decisions you have to make are the toughest, the ones for which there is often no right answer. Pat Chapman-Pincher, a veteran business executive and one of my colleagues at Merryck & Co., a senior leadership development and mentoring firm, shared this insight and others from her decades of experience – as a leader herself, and advising other executives.

Q. What are the most common themes that come up with senior executives you’re advising?

A. There are three. The first one comes up often with new CEOs – it’s the expectation that they’re omnipotent. They’ve typically been promoted into that role because they were good at one or two things, and suddenly they’re expected to be good at everything.

That tends to trigger nervousness and the imposter syndrome, or an unwillingness to admit what they don’t know. The great CEOs learn very quickly what they don’t know, and they’re the people who are quite self-aware and have a certain humility about them. The really dangerous ones are those who think they can do anything they like, now that they’re in control, and they have no idea of the damage they can do.

Q. How do you help them develop their leadership voice around that challenge?

A. The first thing you have to do is get away from the idea that you’re the one who takes all the decisions. Great leaders are there to take the really difficult decisions, and generally they’re the decisions for which neither outcome is necessarily going to be a good one.

"If you find you’re taking really easy decisions, they probably could have been taken by somebody else."

If you find you’re taking really easy decisions, they probably could have been taken by somebody else. You’re there for the ones that keep you awake at night. So that’s one of my litmus tests for whether you’re taking the right decisions – is this a decision that only you can take? 

Q. What is second on your list?

A. The second one that always comes up is whether they’ve got a high-performance or low-performance team. How do they know they’re the right people? How do they motivate them? There are some lessons that have to be learned about what a team is, and that it’s not a bunch of incredibly talented individuals. They have to be able to work together as a team, and there are lessons that have to be learned about chairmanship skills as well as leadership skills.

Q. Getting the right people on the team is something that a lot of leaders grapple with. They have their stars, but some people are in that grey area of being good but not great.

A. Every team needs people who are stars in their own area but you also really need people who do not always want to climb the ladder to take the top role but instead want to do an outstanding job in their current role. You don’t need everybody pushing for the CEO role. 

Q. What’s the third category?

A. The third category is challenging people to think about risk. If the focus is always on turning a small- or medium-sized company into a $10 billion company, then you also have to get people to focus on the risks they face by doing that and how to mitigate them. This is something that companies do not spend enough time on.

I’ve lived through a number of crashes myself, most of which could have, in some way, been foreseen. You need to make sure that your company’s robust so that when the bad times come, as they surely will, you can survive them.

Nobody really wants to think broadly and deeply about things that might go wrong because it’s very negative. But the job of a great leader is to worry about what happens when something does go wrong. The companies that survive are the companies that have survival plans.

Q. Every company in every industry is facing disruption. How do you help senior executives think through those challenges? For some, it can be paralyzing.

A. I do see that, and that’s when people go into denial and start saying to themselves, “Well, this is happening more slowly than we think it might be and so we don’t really need to think about it yet.” I’ve had conversations with chairmen who’ve said, “Well, I can see that’s coming, but I’ll be retired before that.” That was a really frightening thought.

When people do get overwhelmed, you have to sit them down and get clarity about the issues. This can take time, but you need to work out what they’re being overwhelmed by and how they’re going to deal with it, whether it’s their digital strategy, their AI strategy, and how important those issues really are to your business. It’s not just a matter of what you read in the newspapers. How are you going to find out what the issues really are for your industry? And what is their impact going to be on you?

One piece of advice to senior executives is to find all the people in your company who are under 30, get them in a room and ask them what they think about how these trends are going to affect your company. You can’t have a bunch of middle-aged men talking to themselves about it. Somewhere buried in your company, you’ll have some expertise in the disruptors.

Q. And what about you personally? What have been the top two or three leadership lessons that you’ve learned?

A. One is that you need to do less rather than more. As a leader, you’re not paid to be busy. You’re paid to think, to fine-tune the levers rather than yank the steering wheel. It’s all about course correction. You’re there to bring teams of people together and help them to do their greatest work.

"As a leader, you’re not paid to be busy."

The second one is to be utterly ruthless when you need to be. When you have to make a decision among two not-very-good outcomes, then execute hard and execute fast. If you’re going to have to downsize a company dramatically, do it hard, do it once, and make sure you do it with decency. But do not do “death by a thousand cuts” because you don’t have the courage to do it properly. If you are courageous and ruthless, the outcome is always much better.

Q. Where does your drive come from?

A. Early in my career, I had people who believed in me and believed I could do it probably more than I believed in myself. Every time anything has ever come up that I thought was interesting and people asked me to do it, I would say, “Yes, sure.” Then I’d go away and figure it out. Where does that come from? I love a challenge. 

One piece of advice I give people is to never turn down an opportunity. Just do what’s in front of you, do it well and never turn down something because you think you can’t do it. You can generally do a great deal more than you think you can, and nobody is ever completely ready for the next job.