So… I was  enjoying a perfectly good conversation with another business owner I’d just met, discussing how our firms had evolved, similarities and differences in our experience, and so on.  And, then he asked me:

“What keeps you up at night?”

The real answer, for me, is “Not much.”   Since the kids are out of the house and since my wife the nurse doesn’t “take call” for patients,   I sleep just fine, thank you very much.

And, the question, “What keeps you up at night?”  is just a downer because it’s an unimaginative, bottom-dragging (think fishing nets here) question that  calls up emotions and memories from times when family or business worries  DID disturb my sleep, or that I lay awake waiting for a 3:00 am wake up call, or that I couldn’t sleep because someone in the house was coughing.  Just  bummer stuff.

Hot-coals walking / Peak Performance coaching Tony Robbins once wrote, “If you ask a lousy question, you will get a lousy answer, and a lousy emotional state.”

“What keeps you up at night?” is an example of such a lousy question. I wanted to say to my business-owning conversation partner, “Can’t you do any better than that?”

If we’re really interested in our clients’ nocturnal subconscious deliberations… Far better to ask questions that touch more directly the points we’d like to hear, which might go something like…in no particular order…

• “What uncertainties in your clients (or your suppliers, or your employees) are you watching most closely?”
• “How will you know things are going to go one way versus another?”
• “How could you hedge your bets so that you could be OK whichever way it goes?
• “What sorts of resources will you need to hedge or prepare?”
• “What decisions are you delaying or are affected by the uncertainties?”

Or, from a more positive direction:

• “What changes to your business are you thinking about?”
• “What are the issues on which you’re thinking ‘maybe I could do this’ or ‘maybe I could do that?”
• “What’s difficult about those decisions?”
• “What factors are you weighing?”
• “What are the points for and against each side of the argument?”

These questions focus the conversation more clearly than “What keeps you up at night?” without any of the attached baggage.  Second, the questions demonstrate some awareness of how business leaders think and process information. Not a bad thing if one is attempting to sell them or advise them.