The Best Leaders Always Ask These Questions

The Best Leaders Always Ask These Leadership Questions

While exploring potential assignments near the end of my career with the U.S. Navy, I sought out advice from a trusted mentor.

“What’s your goal for the time you have remaining with the Navy?” he asked when we had a chance to sit down for a chat.

When I told him that wasn’t clear yet, he asked another question: “What do you enjoy most?”

“That’s easy,” I told him. “Helping people unleash their potential.”

I’d had the privilege of doing that not only through teaching colleagues how to fly Navy planes but also by leading talented women and men in a variety of assignments over 3 decades.

“Is unlocking potential the kind of thing you want to focus on in your next job?” he asked.

“Now that you put it that way,” I told him, “I believe it is.”

He came back with one final question: “Are your current actions and thinking leading you in that direction?”

I had to admit they were not.

That was a hard realization, and it set me on a new career path, drawing me away from flying and strategic planning and into education and leadership – first as superintendent of the U.S. Naval Academy, then as chancellor of the State University of New York, and now as President of the Center for Creative Leadership.

And it all started with a series of good questions that got right to the heart of things.

Voltaire said we should “judge a man by his questions rather than by his answers,” and that is never more true than in leadership roles.

The most effective leaders are those who develop great diagnostic abilities and thus can cut through seemingly complicated situations and identify the levers that will really make a difference. They have insatiable curiosity, the humility to know they can and must learn every day, and awareness of their own limitations.

They have the mindset of a coach, and coaching, as we’ve explored in the Center for Creative Leadership Handbook of Coaching in Organizations, is not about dispensing advice.

It’s about helping people tap into and act on their own knowledge, it’s about how to have a coaching conversation, and most importantly, the ability to really, actively listen to people’s answers.

These leaders – and I’ve been fortunate to work with and learn from many of them – understand they need the right information to make the right decisions. The only way to get it is by asking for it. Thoughtful questions open lines of communication with our teams, our organizations and, perhaps most importantly, ourselves.

The Best Leadership Questions to Ask

Management pioneer Peter Drucker, a longtime hero of mine, posed The 5 Most Important Questions You Will Ever Ask About Your Organization:

  • What is our mission?
  • Who is our customer?
  • What does our customer value?
  • What are our results?
  • What is our plan?

These questions help you get to the key drivers of value at your organization.

We also need to make time regularly to ask ourselves and our teams some critical questions. These questions work best when they are simple and powerful. Asking powerful questions is a key way to coach your people.

Here are the key questions that excellent mentors have always encouraged me to ask myself:

  • What are the most important big priorities you care about regarding your family, your organization, and your community?
  • Are you investing time with the right people regarding these priorities?
  • What are you doing about each priority?
  • Why are you doing it?
  • How do you feel about it?
  • What would you like to do that you can’t do now?
  • What would your future 85-year-old self, looking back, say you should do?

And these are the core questions that I ask my teams, because great leaders have often asked them of me:

  • What do I need to know about this issue/opportunity?
  • How do we make the most of this opportunity?
  • What do you think?
  • What might we be explaining away a little too quickly?
  • Is this really an either/or choice? What are we missing?

Effective leaders need to continually listen, reflect, and learn. But they can’t do any of those things without asking the right questions first.

Ready to Take the Next Step?

Upskill your team to ask the right questions and really listen to one another’s perspectives. Build their coaching skills and ability to hold coaching conversations and scale a culture of effective feedback across your organization.


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November 9, 2020
Leading Effectively Staff
About the Author(s)
Leading Effectively Staff
This article was written by our Leading Effectively staff, who analyze our decades of pioneering, expert research and experiences in the field to share content that will help leaders at every level. Subscribe to our emails to get the latest research-based leadership articles and insights sent straight to your inbox.

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