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


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?

The Law of Leadership Transparency – 3 ways to apply it

 A business owner shared his survival story from the latest downturn.  When I asked him “What is different about your business now versus three years ago?” his answer made me step back.  He said “Now, my business comes before my people.”  He went on to explain when he hires he tells people up front that he is doing everything he can to keep them busy, but if the business drops off he will have to  send them home.  He also makes it clear that his best people, regardless of tenure, will be kept on as long as he can.

He learned the law of transparency, which is Be open and honest about things you want to face with someone if you expect/need them to help.  

Here are three ways to apply this law:

  • Performance discussion – If this does not feel like a conversation the law is not being applied.
  • Making a sacrifice to manage through a negative event – If people have to sacrifice then they need to know what is happening.
  • Recruiting – What is broken that this role needs to be fixed?  Say it and ask for the help before you offer the job.

Transparency can be taught, but it first has to be valued. 

Leaders who use it effectively are rewarded with trust and respect.