Understanding how leaders make decisions and what motivates them is an important part of connecting them to their team and culture.
While all hiring is important, hiring leaders will pose the greatest opportunity or threat to existing team dynamics. The right leader will enhance the success of an organization while the wrong hire can lead to stress, confusion and even the departure of great people.
Past experience will not reveal the thoughts and behaviors that led to those results. More importantly, past experiences may not accurately predict a leader’s potential future.
Below are a series of questions designed to help companies dig beneath the surface to see how a potential leader might perform. In full disclosure, I have used many 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 a key initiative or strategy you have implemented.
High quality decisions are the bread and butter of leadership. The purpose of this question is to understand whether the interviewer makes an objective judgment or relies solely on gut instinct and opinion. Overconfidence in one’s opinion can often reflect a lake of openness and curiosity. Look for subjective answers, such as “It just made sense to me” or “I’ve done this in all my roles so I’m sure it will work again.”
Under what circumstances in your life and who taught you to think and act this way?
This question attempts to understand the influences of the leader. Listen to language that sounds fear based or trauma based. Does this leader act out of insecurity? Do they feel like they deserve a certain outcome or outcome because of their past? Does it sound like they are trying to enforce a certain attitude?
Give me a practical example of your leadership style.
Leading the conversation to practical examples will give both the opportunity to see how they describe themselves and how they remember events. Do they show humility in describing their style? Does the example seem one-sided or biased in their favor?
Tell me about a situation that affected your approach to leadership.
Similar to the above, this question looks for the underlying influences that will persist if this leader works with you. Were these conditions successful or unsuccessful? Did these situations demand humility and learning? As Jony Ive says, “Success is the enemy of curiosity.”
Follow-up question… If I asked other people on your team, would they agree with what you just described?
See here for the response. 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 one of the options. Leaders have to make tradeoffs as part of their job and it’s important to know what they personally struggle not to say. Do they find themselves saying yes to please people? Do they say yes to saying they can do more?
What do you do when you see your team struggling?
Great leaders know that all problems are ultimately their responsibility. When they share their experiences, how much responsibility did they accept for the team’s struggles? Does the question ask the leader to be disappointed with their previous team’s performance? Do they blame the team for the conflict?
If you could turn back the clock to turn one decision into a leadership role, what would it be and why?
This question provides an 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 arrogance?
Tell me about the conditions you need to thrive and how the company can provide it for you.
Providing the environment for leaders to succeed should be a core competency of any company. Each of us is different so we expect different situations to appear for each of us. In the same way that the leader needs to create a safe space for his team to succeed, we also need to create an environment for the leader to succeed.
How do you optimize 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 leaders will see a change in context as markets change. If a leader cannot adapt to the context he is unlikely to be successful.
Tell me about the development of the people under your leadership.
The awakening that leaders have left are the people they have helped to grow and be successful. The primary role of a mass leader is to be an advocate and an ally to the success of others. What has this leader done to create success for others? Can they show evidence of their positive impact on their teams?
Thank you to all the wonderful leaders who have taught me these questions. Special thanks to Andy La Monica, Robin Longes and Mike Leibovitz.