So… I was enjoying a perfectly good, warm weather, al fresco, cold drink conversation with another business owner I’d just met, discussing how our firms had evolved, similarities and differences in our experiences, and so on. And, then he asked me:
“So, what keeps you up at night?”
The real answer, for me, is “Not much, anymore.” If I were up to anything exotic, I’d be unlikely to share it with someone I’d just met. And, 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.
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 a lousy question. It implicitly focuses our conversation partners on negative stuff, worries, and bad experiences. Bad baggage.
If we’re really interested in our clients’ nocturnal subconscious deliberations… far better to ask baggage-free questions that touch more directly the points we’d like to hear, which might go something like…in no particular order…
- “What challenges or uncertainties in your business are you watching most closely?”
- “What decisions are you delaying or are affected by the uncertainties?”
- “What changes in 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 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.
No more, “What keeps you up at night?”