How Should CEOs Answer the Question, “What Keeps You Up at Night?”

I’ve always felt that “what keeps you up at night?” was a trick question for CEOs.

There’s one part of it I’m quite sure about.  There cannot be anything that you control that keeps you up at night.  Why?  Because you’re the CEO.  If something is keeping you up at night, well, do something about it.

Stress, as I like to say, is for VPs and CXOs.  They’re the ones that need to convince the boss about something.  They’re the ones worried about how something might look.  The CEO?  Well, you’re accountable for results.  You get to make or approve the decisions.

If you’re a founder/CEO then you shouldn’t be particularly worried about how things look to the board.  It’s your company.  You’ve got an invisibility cloak that your hired CEO counterparts lack, and which you should use when needed.  Think of founder privilege the way the kitschy Love Story described love:  it means never having to say you’re sorry.

For what it’s worth, and I won’t claim to have been God’s gift to CEOs, I lived by the control rule — that is, if I controlled it and it woke me up in the middle of the night, then I was going to do something about it.  That’s why one of the worst things I could say to one of my VPs was, “I woke up last night thinking about you.”  If that happened, and it sometimes did, then either our working relationship or their employment status was changing soon.

I put this in the same “listen to your gut” class as the I don’t want to talk to you anymore rule.  If you’re one of my VPs, then you’re running a key part of my company, then I should look forward to speaking with you each and every time.  If I don’t look forward to speaking with you, it’s a massive problem, and one I shouldn’t ignore.  After all, why wouldn’t I look forward to speaking with you?  Who don’t I like speaking to?  People who:

• Don’t listen
• Don’t follow through
• Can’t keep up
• Grinf-ck me
• Can’t or won’t change
• Are negative
• Are mean

There are probably other classes, but the point is if I don’t want to talk to someone, it’s a huge signal and one I should dig into, not ignore.

Waking up in the middle of the night is an even bigger signal.  If you agree that CEOs should not wake up in the middle of the night over things they can control, then we can move onto the second category:  things they can’t control.  Should CEOs wake up in the middle of the night over them?

Again I say no.  Why?

Making bets is a big part of a CEO’s job.  Based on available information and working with the team, the CEO places a set of strategic bets on behalf of the company.  The company then needs to execute those strategies.  While the quality of that execution is under the CEO’s control (and should be high to remove execution as a source of noise in the strategy process), the outcome is not.

Why be stressed while the roulette wheel is spinning?  It’s a natural reaction, but does it change the outcome?  You’ve placed your chips already.  Does stressing out increase the odds of the ball landing on your square?  Does not stressing out decrease it?  No.  It changes nothing at the roulette table.

I’d argue that in business, unlike roulette, stressing out can effect the outcome.  A CEO who’s constantly under stress while the wheel is spinning — e.g., waking up in the middle of the night — is likely to perform worse, not better, as a result.

• A tired CEO does not make great decisions
• A haggard CEO does not inspire confidence
• A grumpy CEO does not handle delicate situations well

I’m not trying to minimize the very real stress that comes with the CEO job.  I am, however, trying to provide a rational, contrarian, and hopefully fresh point of view that helps you better frame it.

In the end, there are two types of things that CEOs can potentially stress about:

• Things they can control.  They shouldn’t stress over these because they should do something about them, instead.
• Things they can’t control.  They shouldn’t stress over these because doing so will not change the outcome.  Worse yet, it may well change the outcome — for the worse — over the things they can control.

Ergo, CEOs should never stress about things.  QED.

As Warren Buffet said, “games are won by players who focus on the playing field — not by those whose eyes are glued to the scoreboard.”  Focus on what you can control and, as Bill Walsh says, the score will take care of itself.

Congratulations.  You’re the CEO.  You’ve got the best job in the world.  Enjoy every day.  And sleep well every night.

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Notes

• To reiterate, none of this is to trivialize the stress that comes with the CEO job nor to suggest that CEOs shouldn’t work hard.  It is to say that I believe they will be happier and more effective if they find a way to sleep well — as most senior executives do.
• To look at this from an outcomes perspective, while I was pleased with the operational results at both companies I ran, I was not particularly pleased with the outcomes.  Did I work hard and obsess about things?  Yes, in general.  If I worried more and slept less do I think it would have improved my outcomes?  No.  Were some of the worst decisions I made in part due to being worried and stressed about things?  Yes.  Did I in general sleep well?  Yes.  I have always naturally focused on running plays well and believed that the score would then take of itself.  In my experience, sometimes it does, but sometimes it doesn’t.
• In writing this post, I found a few anecdotal, fun, and one somewhat ironic article on success and sleep.
• This Bill Walsh quote seems to undermine my argument.  “If you’re up at 3 A.M. every night talking into a tape recorder and writing notes on scraps of paper, have a knot in your stomach and a rash on your skin, are losing sleep and losing touch with your wife and kids, have no appetite or sense of humor, and feel that everything might turn out wrong, then you’re probably doing the job.”  That said, he’d use this as an opener to speeches which were largely about focusing on what you can control.
• Walsh’s other quote on sleep was more proactive:  “If you want to sleep at night before the game, have your first 25 plays established in your own mind the night before that. You can walk into the stadium and you can start the game without that stress factor. You will start the game and you will remind yourself that you are looking at certain things because a pattern has been set up.”