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Leadership Thought #240 – Eight Questions Leaders Should Be Asking All the Time

September 24, 2018

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How focused are you on asking good questions?

As a company grows, a leader’s role becomes less tangible and more symbolic. You graduate from the world of constant “doing” and need to move towards conscious “thinking” and “being.”  Others will take their lead from you.  You will always be a key role model no matter how big the company gets or how many layers of management exist between the front line and you.  If there is a disconnect between what you say and what you do, then everyone will notice it (and more quickly than you think).

As I’ve covered many times in previous blogs, it becomes less and less about you working harder or having all the answers, and more about you diligently asking the right questions and letting others guide you. You need to become an expert “question asker” and never miss an opportunity to interact with all employees in this manner.  There are eight questions that when asked on a regular basis will encourage your people and the company, as a whole, to learn and grow:

  1. What did you learn today that other people in the company should know?
  2. Is there a better, more effective way of doing this?
  3. How can we improve upon what we are already doing well?
  4. How can we make it easier for you to do a good job?
  5. What are we currently doing as management that makes minimal or no sense whatsoever?
  6. How well are we living our cultural values as a company (note: they should know what these are)?
  7. What are you hearing about us or the market from our customers, vendors, or partners?
  8. If you were me, what major changes would you make in the company and why?


Don’t ever get defensive about the answers. In fact, encourage people to speak up and acknowledge their honesty and candor when this happens. You certainly don’t have to act on everything that you hear, but if there is an obvious quick fix that makes sense then act on it right away.  On the bigger issues, use the information you receive as fodder to drive productive discussions amongst your leadership/management team.   Asking good questions and listening to the answers is one of the best skills a leader can develop.