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Are You Asking Enough Questions?

Written by Chuck Olson

The other day I was reviewing some notes from Brad Lomenick’s book The Catalyst Leader and stumbled upon a section with a heading that snagged my curiosity: Seven Signs You’re Too Big For Your Britches. Now, who can resist THAT title, that invitation? Intrigued? Interested?

I was. And I am.

Lomenick parses out his provocative title with seven statements—a proverbial punch list for Kingdom leaders. Take a look at his seven declarations:

  1. You feel like you need an entourage everywhere you go.
  2. You’re unreachable, using systems and handlers to shield you from others.
  3. The only people you make time for are those who can do something for you.
  4. You speak and offer advice far more than you ask questions and take notes.
  5. You quit laughing, especially at yourself.
  6. You feel certain jobs are beneath you and would be offended if someone asked you to perform those tasks.
  7. You feel no one’s work ever meets your approval—except your own.

While each of these are worthy of a personal inventory, allow me to drill down on statement #4: You speak and offer advice far more than you ask questions and take notes.

Have you ever been in a meeting or had lunch with The Pontificator? It’s an avalanche of self-focused (and often self-promoting) declarations. There is little, if any, exchange of ideas. And noticeably MIA in the lopsided conversation is the place and priority of QUESTIONS.

In a word, questions are the launching pad of invention, the springboard of innovation. Great leaders have an obsession for great questions. They possess curiosity, humility, and an incurable posture of learning that shouts out that they are determined to expand their understanding of life and leadership.

Albert Einstein said, If I had an hour to solve a problem and my life depended on it, I would use the first 55 minutes determining the proper questions to ask.

Peter Drucker put it this way, My greatest strength as a consultant is to be ignorant and ask a few questions.

While some people collect coins, others stamps, I propose that a leader collect questions—questions that kick in the door of discovery. Here’s a few of my favorite questions to ask other leaders:

  • What life event has most shaped your life and leadership?
  • What fears have you had to face?
  • What spiritual discipline/practice is most meaningful to the cultivation of your soul?
  • What have you learned from failure?
  • What would you tell your 20-year-old self?
  • What person or author has contributed most to your understanding of leadership?
  • How do you resist being complacent with your life? Your leadership? Your worldview?
  • How do you create space to hear from God?
  • What voices/messages have you had to amplify (or turn down) in your life and leadership?

Have some fun curating your own list of questions. But most of all, make a commitment that in your upcoming one-on-one conversations to speak less and ask more. The odds are in your favor that you’ll walk away a fuller, richer leader.


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Chuck Olson

As founder and president of Lead With Your Life, Dr. Chuck Olson is passionate about inspiring, resourcing and equipping Kingdom leaders to lead from the inside out.  To lead, not with the external shell of positions, achievements or titles, but from an internal commitment to a deep, abiding and transparent relationship with Jesus. Serving as a pastor and leadership coach for over forty years, Chuck has a track record of building these truths deep into the lives of both ministry and marketplace leaders.

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