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Years ago I heard leadership coach and author Bob Biehl say that he loves to collect questions.  That thought intrigued me.  So since that time I’ve been a student and collector of questions.

Lou Holtz once said, “I never learn anything talking. I only learn things when I ask questions.” Questions challenge us to see things from a different perspective and guide us to breakthrough behaviors.  You can be stuck and discouraged in one moment but with the aid of the right question, an instant later you’re flooded with fresh ideas and motivation.

Here are 12 of my favorite questions.  Chew on a few of these today and see what new insights or direction you might discover.

  1. What would a great leader do in this situation?  (Bill Hybels, Pastor Willowcreek Community Church)
  2. What do I believe is impossible to do in my field, but if it could be done, will fundamentally change my business? (Joel Barker, author of Paradigms)
  3. What is the wise thing to do?  (Andy Stanley, Pastor Northpoint Church)
  4. What is the single best measurable indicator that I am making progress toward my dream? Bob Biehl
  5. What are the “elephants” in my schedule? (Pareto said, “If you’re Noah, and your ark is about to sink, look for the elephants first.”) (Don’t know who asked this one but I like it)
  6. How can we become the company that would put us out of business? (Danny Meyer, CEO of Union Square Hospitality Group)
  7. What counts that we are not counting? (Chip Conley, head of global hospitality for Airbnb)
  8. What should we stop doing? (Peter Drucker, management expert and author)
  9. What are the gaps in my knowledge and experience? (Charles Handy, author and management expert)
  10. If we got kicked out and the board brought in a new CEO, what would he do? (Andy Grove, former CEO of Intel )
  11. What advice would you give you if you were in your situation? (Came as a result of me having a pity party about my own situation several years ago)
  12. What questions do you have that you’d like answers to?  (From Action Learning Method)

Here’s one more bonus question, undoubtedly the most important question you can answer, “Who do you say I am? (Jesus, Mark 8:29)

What great question do you like to wrestle with?



You’re frustrated because your new leader isn’t working out like you thought. When they first started they were so enthusiastic. But now their commitment is waning, they seem complacent and if you’re honest they’re not being very effective.

This scenario is repeating itself way more frequently than you’d like and you’re getting discouraged. So you find yourself in that same old place of asking, “What’s wrong with these people?”

If this is a reoccurring issue then chances are you don’t have a people problem, you have a system problem.

Think of someone in your area of ministry that fits this scenario. Now let’s ask some diagnostic questions:

  • Did you screen them ahead of time by having them complete a questionnaire identifying their Gifts, Passion, Personality and past experiences?
  • Did you give them a season to pray and observe the ministry in action before they said “Yes” to serving in the role?
  • Did you meet with them 1-1 to discuss role and responsibilities?
  • Did more than one person interview them and agree they were the right person for the role?
  • Did you give them a written role description and go over it with them?
  • Did you provide training in the specific skills you expect for that role?
  • Are you providing ongoing communication, support and development?
  • Are you providing feedback on their strengths and growth areas?
  • Are you providing the opportunity for peer to peer learning?

Most leaders haven’t received this type of systematic onboarding and development. So let me ask: Is the Core Problem THEIR SKILL or is the Core Problem YOUR SYSTEM?   A strong system can produce a strong leader.

Approach #1

Talk, talk, talk. Talk, talk, talk, talk. Talk some more, a little bit more, and just a little more. And now end by talking.

Approach #2

Ask a question. Another question, another and yet another. Ask a self-assessment question. Ask an observation question. Ask about their point of view.  Ask about their past experience.  Ask their opinion.  And ask an insight question.

Now share an insight from your experience. Now back to asking a question.  Another question and another question.

I’ll leave it to you to decide which you believe is the better approach.