What keeps you up at night? A unique way to use this question

by Feb 17, 2011Insights, Interesting People, Leadership


We have all heard this question.  It is one of those What to ask a leader 101 questions.  Yesterday I heard this question used in a way that surprised me.

I saw retired Brigadier General David Hall speak.  He had many insights to share, but how he used this question was unique.  In his years of leading he developed the habit gathering his staff together at the end of each month to have a drink and some social time.  One of the things he would do during their time together was share the things that, as their leader, were keeping him up at night.  He would end with the request for help from anyone who had an idea or perspective that would make that worry go away. 

  • Shouldn’t people ask the leader this question?  Yes, but the military is not much different from business.  Sometimes people are scared or nervous to ask a leader a tough question.
  • Is it right for a leader to dump like that?  It is sharing what you are thinking and asking for help.  Dumping is this happening daily or weekly.

Not surprisingly, many of his problems went away over time. 

Why wait for a question like this to be asked first?

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