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What Keeps You Up at Night?

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"What keeps you up at night?" along with "What is your greatest weakness?" are perhaps the two most frequently asked questions 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 answer.

Joann Lublin's excellent career column in the Wall Street Journal offered advice about how to handle the interview FAQ, 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 rather than 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."

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, in 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, there is no room whatsoever to evade. Accountability is all. Tell your questioner what keeps you up at night, but then, immediately add the measures you are taking to correct what keeps you up at night. "What keeps me up at night is ______, and what I'm doing about it is _____."

In the wake of the Tom Daschle affair, Barack Obama went on primetime television to address the matter in a series of interviews with the major news anchors. He told CNN's Anderson Cooper, "I think I screwed up. I take responsibility for it, and we're going to make sure we fix it, so it doesn't happen again."

But making sure it doesn't happen again is only a retrospective action and not sufficiently corrective; closing the barn door after the horse has gotten out. The president is going to have to say what he is going to do about it prospectively. As the New York Times' Frank Rich cautioned, "Even as President Obama refreshingly took responsibility for having 'screwed up,' it's not clear that he fully understands the huge forces that hit his young administration last week...The new president who vowed to change Washington's culture will have to fight much harder to keep from being co-opted by it instead."