The Wrong Leadership Question

01.19.2022 / Leadership Development

It is the most overused question in the history of business. I remember first hearing it over two decades ago during the recession of 2001, and at the time I knew there was something I didn’t like about it. That sentiment has only grown stronger with each passing CEO presentation or company town hall meeting where, inevitably, the question gets asked. Previously, it bothered me because it showcases leadership anxiety, but now it just bothers me because the question is stale and unoriginal. So what’s the leadership question?

What keeps you awake at night?

There are so many things wrong with this question that I could write ten blog posts. But at the risk of spiking my blood pressure, I’ll just stick to my bigger beefs. First, if we’ve learned anything about human performance in the last fifteen years, it’s that focusing on one’s strengths has far more impact than obsessing about one’s weaknesses. Yet our silly little question about nocturnal disturbance focuses precisely on what’s wrong, broken, or failing. The question gets a leader to focus not on what’s going right in their business, but on what they fear will go wrong. It’s not a strength-based question; it’s a weaknesses-based question.

Don’t Focus on Fears

Second, the question is fused with anxiety. The question behind the question is really, “What do you worry about a lot?” By answering, the leader gets to showcase – or worse, transmit – his or her fears. There is a subtle insinuation that if everyone in the workforce would just make whatever the leader is worried about their priority, the leader would be able to sleep more soundly at night. In other words, if everyone were woken up by this problem, whatever it may be, then the leader wouldn’t have to worry so much. Doesn’t putting the workforce on a leader’s twenty-four-hour fear cycle seem perverse to you? Seriously, insomnia shouldn’t be a leadership badge of honor.

My final beef with the nightmarish question is that it is completely overused. There is nothing inspired, original, or imaginative about it. In resorting to its use, the questioner exercises none of his or her curiosity, thoughtfulness, or intelligence. Asking the question has the same intellectual heft as asking “How’s the weather?”

So what’s a better question to ask? How about a question that prompts a leader to talk about the opportunities on the horizon? What about a question that gets a leader to clarify where the organization is headed and why that destination is so worthwhile and compelling? What about a question that taps into the leader’s formative lessons and how those lessons shape the leader’s viewpoint? How about a question that showcases the leader’s confidence, optimism, and deep belief in the workforce? How about instead of asking what keeps the leader awake at night we asked:

What gets you up in the morning?

Updated Jan. 2022

Photo by Geralt on Pixabay.

About Bill Treasurer

Bill Treasurer is a bestselling author, leadership consultant, and creator of Q Cards. He is the founder of Giant Leap Consulting, a courage-building company, and the author of the international bestseller, Courage Goes to Work. His workshops have been taught to thousands of executives in eleven countries on five continents. For more than two decades, Bill has designed and delivered programs for emerging and experienced leaders from such organizations as NASA, Saks Fifth Avenue, Lenovo, eBay, UBS Bank, Spanx, the Pittsburgh Pirates, and the U.S. Department of Veterans Affairs. Prior to founding Giant Leap Consulting, Bill served as an executive in Accenture’s change management and human performance practice, eventually becoming the $35 billion company’s first full-time internal executive coach.

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What People Are Saying

Joy Guthrie | Jul 31, 2013

I get what you’re saying. The answer to both questions is very instructive for the person asking the question. It seems a lot like “imagine this has succeeded, what went really well” vs “imagine this failed, what went wrong.” Having answers to both sides of the question provides insights that can be actionable. As a leader, I definitely would prefer to focus on “what gets you up in the morning.” As a manager, I would want to know what risks/fears are out there to create great mitigation and communication plans to insure success.

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Chery Gegelman | Aug 02, 2013

Bill – You make such a great point! What we focus on drives our behavior!

The first time I was asked that question I was a mid-level manager and the CEO asked me, “What keeps you up at night?” I was immediately interested, because it was such a probing question that invites authenticity and vulnerability.

At the same time I absolutely agree with you, that dewelling on fears, or worse yet speaking them out loud keeps us focused on the things we fear. It can consume our thinking , sap our energy and cause the very thing we fear to become a reality.

Great post!

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Lynn Ferguson-Pinet | Mar 19, 2014

Love this post, I’m often called an eternal optimist but I’d rather approach the world with that view point. I also love the concept of strength based questions. I often ask clients to identify one thing they can improve during their team building event, I’m going to refocus that to have them articulate their greatest strength on the team.

Thanks
Lynn

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