10 Thoughtful Questions For Interviewing Leaders

Published on
August 15, 2023

While all hires are important, hiring leaders will pose the biggest opportunity or threat to an existing team’s dynamic. The right leader will amplify an organization's success while the wrong hire can lead to tension, confusion, and even the departures of great people.

Past experience won’t reveal the thoughts and behaviors that led to those outcomes. More importantly, past experiences can’t accurately tell about the leader’s potential future.

Below are a series of questions that have helped companies dig below the surface to get a glimpse of how the prospective leader might perform. In full disclosure, I’ve used several of these questions when interviewing leaders for the Product Leadership and Design Leadership books. The journalistic nature of these questions can help in many situations.

Describe your decision-making process on an important initiative or strategy you’ve executed.

High-quality decisions are the bread and butter of leadership. This question aims to understand whether the interviewee makes objective decisions or relies entirely on gut instinct and opinion. Overconfidence in one’s opinion can often reflect a lake of openness and curiosity. Look out for subjective answers like, “It just made sense to me” or “I’ve done it like this in all my roles so I felt confident that it would work again.”

What situations, and who in your life, taught you to think and act like this?

This question seeks to understand the leader’s influences. Listen out for language that feels fear based or trauma based. Does this leader act out of insecurity? Do they feel like they deserved a certain outcome or result because of their past? Does it feel like they are trying to enforce a certain attitude?

Give me practical examples of your leadership style?

Moving the conversation toward practical examples will provide opportunities to see both how they describe themselves and how they remembered the events. Do they display humility in how they describe their style? Does the example feel one-sided or biased in their favor?

Tell me about a situation that influenced your approach to leadership?

Similar to the above, this question looks for underlying influences that will persist when this leader works with you. Were these situations successes or failures? Did these situations solicit humility and learning? As Jonny Ive says, “Success is the enemy of curiosity.”

Follow-up question… If I asked the other people on your team, would they agree with what you’ve just described?

Watch for the reaction here. Look for consistency and humility in their response. Do they react with defensiveness or curiosity?

What do you struggle to say no to?

We all have to choose between options. Leaders have to make tradeoffs as part of their work and it’s important to know what they personally struggle to say no to. Do they find themselves saying yes to please people? Do they say yes to create a sense they can do more?

When you see your team struggling, what do you do?

Great leaders know that all problems ultimately are their responsibility. As they share their experiences, how much responsibility did they accept for the team’s struggles? Does this question solicit frustration from the leader with their past team’s performance? Do they blame the team for the struggles?

If you could turn the clock back to change one decision you’ve had to make in a leadership role, what would it be and why?

This question extends the opportunity for the leader to share the lessons learned. Does this leader focus on moments that show growth and understanding? Or are these stories mostly about regret and ego?

Tell me about the conditions you need to thrive and how can the company provide that for you.

Providing an environment for leaders to be successful needs to be a core competency of any company. Each of us is different so we’d expect to see different conditions for each of us to thrive. In the same way, the leader needs to create a safe space for their team’s success, we also need to create an environment for the leader to be successful.

How do you adapt your approach in driving performance to achieve team and business objectives?

Context is everything. No leader will experience the exact same team or business environment. Even the same leader will see changes in context as markets change. If a leader can’t adapt to the context then they are unlikely to succeed.

Tell me about the growth of people after they’ve been led by you?

The wake that leaders leave behind is the people they’ve helped grow and succeed. Being an advocate and ally for others’ success is the primary role of a people leader. What has this leader done to create success for others? Can they show evidence of the positive influence they’ve had on their teams?

Thank you to all the amazing leaders that have taught me these questions. Special thanks to Ande La Monica, Robin Longes, and Mike Leibovitz.


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