5 Great Questions The Best Leaders Ask Themselves

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Guest Post by John Kramp

Apparently, few people ask leaders questions about leadership.

Since launching the Your Leadership Story Podcast with my business partner, David Atchison, we have had a great time interviewing exceptional leaders. Without exception, these leaders have  said, “No one has ever asked me that before” to at least some of our questions. That’s unfortunate because these leaders had great answers. All they needed was someone to ask the questions. In a perfect world I can imagine, more people would ask leaders great leadership questions. Doing so would help those asking the questions while helping the leaders reflect on their experiences. Since I cannot control how many people ask leadership questions, I’m opting for an alternative route. If you’re a leader and want to become even more effective, take the initiative and ask yourself some great leadership questions. To get you started, here are some questions David and I have enjoyed asking on Your Leadership Story.

Question 1: Philosophy of Leadership

We probe this area in a variety of ways but we focus on getting to the core of a leader’s perspective.

“If you had to capture your philosophy of leadership in a sentence or two, what would you say?”

We’ve found that every leader can give a long answer about leadership but find it much harder to give a short answer.

If we asked you that question, what would you say?

Question 2: Transition Lessons

Through trial and error, David and I have discovered that some of the most important insights leaders share come from key transitions in their careers. Here’s an example of how we probe these areas.

“We noticed on Linkedin that you made a big shift when you went from Position A to Position B. Tell us more about how you decided to make that move and what you learned from it?”

If we asked you that kind of question, what would you say?

Question 3: Best Boss; Worst Boss

Our friend, Steve Hays, of the Human Capital Group gave us this question and we love to ask it.

“Without naming names, we would like for you to think about the worst boss you ever had and tell us three words you associate with that person. Now, we would like for you to do the same thing with the best boss you’ve ever had using three words.”

As a top-tier executive recruiter, Steve Hays discovered that knowing these six terms — three about a person’s worst boss and three about someone’s best boss provide great insights. “People work hard not to be like their worst boss,” Steve Hays explained, “while trying to be more like their best boss.”

We agree. When we ask people this question, light bulbs come on. What would you say if we asked you this question?

Question 4: Percentage of Leadership Insight

We ask this question in different ways depending on the background and experiences of the leaders we’re interviewing, but here’s an example.

“We would like for you to think about 100% of what you know about leadership at this point in your career and then see if you can divide that 100% into the main sources for what you know. For example, what percentage came from your formal education? What about from the first phase of your professional career? What about from the most recent phase of your career?”

Tough question, right? Absolutely. But the answers can be profound, especially as leaders reflect on how they actually learned to lead the way they do.

What would you say if we asked you that question?

Question 5: The Rough Patches

The leaders we interview have impressive resumes. We enjoy hearing more about the exciting things they have done. However, we work hard to dig into the times when things didn’t go as well. Here’s an example of what we ask.

“Reading through your resume is like taking a fast elevator up a skyscraper. It looks like you’ve gone no where but up. Were there any rough patches along the way? Can you tell us about one that stands out in your mind and how that experience shaped your leadership story?”

Every leader has a “rough patch” and talks about it when asked. In fact, it is often during those “rough patches” that leaders gain their most important insights and develop their deepest convictions.

What would you share with us if we asked you this question?

The Importance of Answering Great Questions After doing so many of our leadership interviews, we’ve been surprised at one recurring response from the men and women with whom we talk. After we complete the interview, they say in different ways, “Thanks for giving me the chance to think about these questions.” That’s the problem — they had answers; they simply needed someone to ask the questions, not just for people listening but for themselves, so that they as leaders could reflect on their own experiences. I hope someone asks you great leadership questions today. Answering those questions will make you a better leader. But if you go through the day and no one asks, take the initiative and ask yourself. The best leaders do. Shouldn’t you?

What about you?  What’s the best question you’ve been asked about your leadership or that you have asked another leader?

JohnKrampJohn Kramp is the Senior Vice President of The Bible Group at HarperCollins ChristianPublishing  and is Co-Founder and Partner of The Riverstone Group.   Previously he was Division President and Corporate Vice President at LifeWay, based in Nashville. Before his 20-year business career, John led churches for 15 years in Texas and Oregon.  John has published three books including, On Track Leadership: Mastering What Leaders Actually Do.

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