The Best Leaders Always Ask These Questions

The Best Leaders Always Ask These Leadership Questions

What are the types of questions that leaders should ask? Our former President & CEO John Ryan used to tell this story about the power of a leader asking good 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 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’s what set me on an entirely new career path.

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 ask good questions. To do this, they 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 an 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, it’s about the ability to ask powerful questions and then really, actively listen to understand people’s answers.

Leaders know they need the right information to make the right decisions. The only way to get the information needed 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

So, what are the types of questions leaders should ask? A good place to start are the ones management pioneer Peter Drucker 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 can help you get to the key drivers of value at your organization.

And there are other questions leaders can ask their colleagues and teams around the organization to better understand complex situations, untapped opportunities, and unspoken reservations:

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

Leaders also need to make time regularly to reflect, asking themselves questions to increase their own self-awareness, and asking their direct reports questions to build understanding, value alignment, and engagement. These questions work best when they are simple and powerful. Asking powerful questions is a critical part of how to coach your people.

Here are some powerful questions leaders and mentors can ask of themselves and others:

  • 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?

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 make sure leaders are asking good questions and really listening to understand one another’s perspectives. Build their coaching skills with conversational skills training to scale a culture of effective feedback, communication, and collaboration across your organization.

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November 9, 2021
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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