What Keeps You Up at Night?

“What keeps you up at night?” and “What is your greatest weakness?” are perhaps the two most frequently asked questions (FAQs) in business—the first in presentations and the second in interviews. Yet both questions, by their frequent recurrence, are traps for glib answers that could derail the person who provides the answers.

Joann Lublin’s column in the Wall Street Journal offered valuable advice on how to handle the interview question about weakness, starting with what not to say. She provided a long list of common glib answers, ranging from “I am a perfectionist” to “I am a workaholic”—all of which offer a strength instead of a weakness and, therefore, appear evasive. Lublin recommended better, more candid answers, such as having a “tendency to make decisions too fast.” But then she concluded with the most important piece of advice: that any answer to such a question should “cover your corrective steps.” 

This same advice is also applicable to the “What keeps you up at night?” question in presentations. That question has become as much of a ritual in presentations as saying “Cheers” when giving a toast. The question is phrased in those exact words. Not “What problems do you foresee?” Not “What can go wrong?” Not “What are your threats?” But “What keeps you up at night?”

What should you say in response?

What not to say in reply to this question is to make a joke about newborn babies, neighbors’ dogs, faulty air conditioners or the like. Everyone has heard every variation on that lame theme. What to say must be purely candid—a direct answer to a direct question. In business, evasion is not an option. With almost daily revelations of public corruption that are met with denial, evasion, or blaming others, transparency has become more important than ever.

Be frank. Tell your questioner what keeps you up at night, but then, in a parallel to Lublin’s advice in interviews, “cover your corrective steps” by immediately adding what actions you are taking to correct those issues. “What keeps me up at night is       , and what I’m doing about it is       .”

I recently worked with a CEO who was asked “What keeps you up at night?” by a potential investor. The CEO started his response by saying, “What’s top of mind for me is…” in doing so, he teed up a proactive response. Then he went on to say what he was doing about it. Here’s his entire answer:

“What’s top of mind for me is finding the right talent to turn out new versions of our product. What I’m doing about it is a three-pronged approach to develop our headcount: incentivizing our current employees to bring in their friends, recruiting from the top universities, and attending industry conferences to meet new potential hires. That effort alone has already netted a ten percent increase in our software developer staff.” 

Accountability and “corrective” solutions will let you sleep through the night. 

This blog is an excerpt from my book Presentations In Action published by Pearson. Also check out my newly released Presentation Trilogy—Presenting to Win, The Power Presenter, and In the Line of Fireavailable on Amazon and other retailers.