10 thought-provoking questions to ask other leaders

Why would you talk to others about their leadership journeys?

If you’re an executive coach, it’s an essential part of the job and can help drive clients’ internal reflection. Mentors, whether in a formal position or a casual advisory role, can also leverage storytelling to encourage introspection and improvement. Regardless of the relationship, any leader can use questioning techniques to invite exploration, professional development and personal growth.

As Vistage Chair and longtime executive coach Niels Lameijer explains, “Awareness is the first step toward change. Being aware of one’s journey and what shaped them — the good, the bad, and the ugly — is crucial for becoming a better version of themselves.”

Sharon Stein, who facilitates Vistage peer advisory groups, agrees. “I believe as authentic leaders, we must share our mistakes and successes, as we learn from both,” she says.

In the words of Vistage Chair Chris Quinn: “The process of communicating to others opens the leader up to additional questions, which in turn often lead to deeper self-discovery.”

Uncovering leadership lessons was an impetus behind Kevin Trout’s radio program Three Rivers Leadership, now a nationally syndicated podcast. In one-on-one conversations with successful CEOs and entrepreneurs, he probes leadership styles and stories. He finds that asking about a leadership journey offers a unique opportunity to take stock. “Sometimes the feedback I hear is that they didn’t recognize the significance of events until they’re asked to present,” he explains.

Are you looking to elicit meaningful conversations from your executive peers or individuals you lead, coach and mentor? If so, here are a few inquisitional directions you may want to try.

1. Gain insights from personal inspiration

Vistage Chair Marty Stowe often asks his peer advisory group members about a leader they consider an inspiration. The question, he says, “is powerful as it shows the behaviors and ethics a person believes in. It is very telling of how a leader will conduct themselves during times of stress and uncertainty, by following the same behaviors as their mentor.”

Lameijer, who asks a similar question in many coaching sessions, says that bringing to mind a mentor “helps a leader focus on areas where they aspire to better themselves.”

2. Mention motivation

Stowe and Lameijer frequently proceed from inspiration to motivation. Asking “What is your main motivation in leadership?” dives into a client’s core “why,” according to Lameijer.

Stowe explains that understanding the motivation to pursue leadership as a career path is critical because “If their ‘why” isn’t strong enough, they will stumble when faced with large obstacles.”

3. Explore goals and challenges

In many coaching interactions, Trout talks about the past and then looks toward the future, using two related lines of inquiry:

• What was the biggest challenge you were faced with last year and how did you overcome it?
• What’s the biggest decision you must make this year and what’s keeping you from making it?

Those are tough ones but they’ll quickly shape immediate action items.

4. List strengths and weaknesses

Self-awareness is the hallmark of a great leader, so Stowe has leaders enumerate their strengths and weaknesses.

Sounds basic, right? But the question serves a deeper purpose. “Too many people can rattle off the strengths but find it difficult to describe their weaknesses,” he states. “The best leaders know what they are good at and where they need to surround themselves with others who can augment their talents.”

5. Recount a decision-making failure

Many of Stein’s favorite questions center on a leader’s decision-making process. “I ask them to share a decision that did not go well. We talk about the result, what they would do differently, and the impact it had on others, the organization and themselves.”

In a variation on the theme, Trout typically probes about recent decisions the leader regrets and always asks why. Quinn wants to know when the leader has been wrong about a particular topic.

When discussing failures, leaders may initially deflect, Lameijer observes. He urges them to refocus on their own role by asking “Where are your fingerprints on this situation?”

6. Discuss risk and reward

Closely tied to failure is the concept of risk. Stowe highlights two insightful questions:

• What is a risk you have taken in your career that has paid off?
• What risk have you taken that has failed?

He believes that great leaders know how to take calculated risks, so he uses these conversations to assess and enhance risk tolerance and resilience.

7. Ask for reading recommendations

Both Trout and Stowe are apt to talk about books, asking what reading material shaped a leader into who they are today.

Why head down this route? “If a person is reading, it shows they are continuing to learn and grow. What they read indicates areas they’re curious about and seek to improve themselves,” says Stowe.

Lifelong learning is critical, in his opinion. “There is no constant. If you are not growing, you are falling behind in your craft,” he explains. That’s why he’s a proponent of asking this question as well: “How do you continue to grow as a leader?”

8. Next generation

“If you delivered a commencement address today, what would be your message to the graduating class?” Trout recommends this question to bring out important lessons a leader would share with others.

Want to come at it a different way? You might ask a leader what they would tell their younger self or what the best advice they ever received was and how it influenced their journey.

9. Distinguish leadership from management

This one will throw some leaders for a loop because it’s not solely about the leader themselves. “How do you encourage great ideas from your workforce?”

Stowe says the answer can help separate true leaders from mere managers. As he puts it, “Leaders inspire new ideas and stimulate curiosity. Managers simply tell people what to do and can suffocate creativity. This question will indicate if a person has the heart of a leader.”

10. Reflect on the big picture

There are many ways to zoom out and get a “10,000-foot view” of leadership. Trout likes leaders to summarize their life stories in a single sentence. Stowe looks for the one accomplishment about which the leader is most proud. Quinn investigates pivotal points in the leadership journey, times when a cherished perspective changed.

No matter which questions feel most natural and what phrasing works best for you, the keys to a thought-provoking leadership conversation are these: Have the courage to ask and the wisdom to sit back and listen.

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