Two Questions Every Leader Should Ask Themselves


Asking questions is an important skill for any leader.  A good question can create tremendous insight, for themselves and  those around them.  But what makes a good question?  Some leaders believe they need to ask a lot of questions.  This can be helpful but it is often counterproductive.  It can feel like an interrogation and that quickly breaks down trust.  The leader comes over as wanting to understand every detail.

A good question creates insight

A good question creates insight by causing the recipient to think differently.  I recently came across a couple of questions from Hal Gregersen.  He is the author of “Questions Are the Answer: A Breakthrough Approach to Your Most Vexing Problems at Work and in Life”.  Hal’s questions are simple and very insightful:

When was the last time I was asked an uncomfortable question? 

When was the last time I was dead wrong? 

At first glance you may wonder what’s the big deal.  These questions drove me to think deeply.  When was the last time I experienced these things?  At first I couldn’t remember but as I thought about them a couple of examples came to mind.

I couldn’t ignore the answers to these questions

A prior colleague who is also a coach asked me what I am working on to further develop my coaching skills.  This was an uncomfortable question.  I didn’t have a good answer.  There are several things I am always working on but I realized I haven’t made a commitment to further develop a specific skill.  It provoked me to take action.  Firstly, to reflect on what I should be working on and then to determine how.

The second question also pushed me to think hard and an example didn’t come to mind.  And then, it hit me.  A friend had stated his opinion about a coaching assessment that I disagreed with.  In the back of my mind I felt very confident.  I was more skilled than my friend, and I knew best.  That is until I came across the specific issue in a manual which showed me I was wrong.  Dead wrong.

It was good to learn the correct answer, but it taught me something much more important.  Don’t believe everything you think.  I was convinced I was right and that caused me to overlook the facts.  Where else I am doing this?

In both cases the questions caused me to think deeply and differently.  These are two questions I will ask myself on a regular basis.  How about you?