65. What Keeps You Up at Night?: How to Handle the Most Frequently Asked Questions

“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 career column in the Wall Street Journal offered advice about how to handle the interview FAQ 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. Ms. 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.”^F65.1

This same advice is also applicable to the “What keeps you up at night?” question in presentations. That question has become ritual in every type of presentation and every type of business. It 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 universal question is to make a joke about newborn babies, neighbors’ dogs, 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 immediately add what actions you are taking to correct those issues. “What keeps me up at night is ______, and what I’m doing about it is _____.”

Accountability is all.