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10 of the Greatest Leadership Questions Ever Asked

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One of the best skills a leader can develop is the art of asking the right questions – and, even better – at the right time.

Have you ever heard the phrase, “There are no bad questions”? 

In leadership, this might be true. 

In all my years of leadership, I have learned that I only know what I know. And, many times I don’t know much. There are often things among the people I am trying to lead which I need to know – and, for whatever reason – I won’t know unless I ask. Which means I must continually ask lots of questions. 

One of the best skills a leader can develop is the art of asking the right questions – and, even better – at the right times. 

Here are 10 of the greatest leadership questions ever asked: 

  1. How can I help you? 
  2. What is the biggest challenge you have to being successful here? 
  3. Do you understand what I’ve asked you to do? 
  4. What am I missing or what would you do differently if you were me? 
  5. What do you see I can’t see? 
  6. How can I improve as your leader? 
  7. If we had authority to do anything – and money was no barrier – what would you like to see us do as a team/organization? 
  8. Where do you see yourself someday and how can I assist you in getting there? 
  9. What are you currently learning which can help all of us? 
  10. How are you doing in your personal life and is there any way I can help you?
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