Dumb Questions Leaders Ask

Questions leaders ask can, as Geoffrey Colvin said, ” [dumb questions] cut to the heart of the matter, posing a blunt challenge to someone or something…”.  As I mentioned in an earlier blog post [Think Like A Leader], I believe preventative leadership is based on strategic thinking and proactive questioning.

I combined Peter Drucker’s  penchant for asking probing questions that make managers think with Colvin’s observation that even a dumb question can cut to the heart of an important matter.  In doing so, I set about creating a list of questions that smart, proactive leaders should be asking their followers.  I believe the answers to these questions may create an environment in which preventive leadership can take root and flourish.


4 Dumb Questions Leaders Ask:


  1. How Am I Doing?
  2. What Have I Screwed Up Lately?
  3. What Should I Be Doing Better?
  4. What Would You Like Me To Do About That?


How Am I Doing?

It is easy for leaders to allow themselves to become isolated, even insulated from the followers they are entrusted to lead.

If you don’t ask your followers this question, your only alternative would be to trust the opinions of your advisors–most of whom are even further removed from your followers.


What Have I Screwed Up Lately?

Mistakes, errors, miscalculations, screwups — those are the things that can really teach us something.  Spend focused time seeking out areas where you seem to be messing up.  Shine a bright light on those areas so you can begin to proactively repair them.  Although this may be hard, it is one of the most important questions leaders ask.


What Should I Be Doing Better?

There’s always room for improvement.  Go out and ask your followers what they would like to see done better, sooner, at a more sophisticated level.  Yes, their answer may prove to shake your comfort zones. However, they may also serve as the catalysts and personal motivation necessary to move you forward.


What Would You Like Me To Do About That?

Some may categorize this as the dumbest question of all.  Therefore, I would say this is one of the smartest questions leaders ask.   Everyone has an opinion, but possibly the smartest thing a leader can do is actively seek out the other people’s personal, specific opinion.


Questions Leaders Ask


How It’s Done

Now that we’ve briefly covered the four good dumb questions leaders ask, I will tell you how it’s done best. [For the in-depth version, check out my book Leaders Ought To Know First, don’t label your question as dumb.  Secondly, don’t apologize for asking the question.  Third, don’t worry about what the answer might be.  Finally, don’t be intimidated if people don’t immediately offer a response.

Asking questions requires even the best leaders to move past their fears.


Need Help Getting Your Leaders & Teams to Deliver Better Results? Let’s Talk About It.

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Phillip Van Hooser
Author: Phillip Van Hooser
Phillip Van Hooser, CSP, CPAE is committed to helping organizations transform their business outcomes by building engaged employee relationships. He is an award-winning keynote speaker and author on leadership, service and communication. His popular book, “Willie's Way: 6 Secrets for Wooing, Wowing and Winning Customers and Their Loyalty” recently hit #1 in Customer Relations on the Kindle store. Connect with Phil on LinkedIn and Facebook.

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