GUEST POST: The Wrong Leadership Question

It is the most overused question in the history of business. I heard it first about a dozen years ago during the recession of 2001. At the time, I knew there was something I didn’t like about the it. That sentiment has only grown stronger with each passing CEO presentation or company town hall meeting where, inevitably, the question gets asked.

Before, it bothered me because it showcases leadership anxiety. Now it just bothers me because the question is stale and unoriginal. So what’s the question?

What keeps you awake at night?

There are so many things wrong with this question that I could write ten posts about it. 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.

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 the question. 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?

Instead of asking what keeps the leader awake at night, how about we ask this:

What gets you up in the morning?


QUESTION: What are some other powerful questions you have used to “open doors?”


BillTreasurerBill Treasurer is the Chief Encouragement Officer of Giant Leap Consulting and author of Leaders Open Doors, which focuses on how leaders create growth through opportunity. 100% of the book’s royalties are being donated to programs that support children with special needs. Bill is also the author of Courage Goes to Work, Right Risk, and Courageous Leadership, and has led courage-building workshops across the world for NASA, Accenture, CNN, PNC Bank, SPANX, Hugo Boss, Saks Fifth Avenue, and the US Department of Veterans Affairs, and many others. Contact Bill at, or on Twitter at @btreasurer.


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