4 Leadership Interview Questions to Hire the Best Managers

Strong leaders are crucial to the success of your organization. In addition to setting organizational goals and strategy, leaders are also responsible for recruiting and retaining your team. These executive leadership interview questions can help you assess the best management candidates for your team.

What is your proudest leadership moment?

The candidate’s answer to this question can tell you a lot about their leadership values and management style. Ideally, the candidate’s proudest leadership moment would align with your organizational values. If your organization is impact-driven, a good candidate may be proud of hitting an aggressive goal. Or if your organization values education, a good candidate may be proud of mentoring and developing an employee who has become very successful in their career. A candidate may have a wide variety of proud leadership moments. Don’t be afraid to get a little more specific with follow-up questions if you want to know about a time they hit an aggressive sales goal or developed an employee.

Tell me about a time when you failed as a leader.

This is a spin on asking the candidate about their greatest weakness, and helps you get a more well-rounded view of the candidate. Managers aren’t perfect all the time, but you want to see that they recognize their mistakes and learn from them. Ask the candidate what they should have done differently, and what kept them from doing that. While this brings up a hypothetical situation, you want to see that it aligns with the behavior you’d expect of managers in your own organization.

How do you provide feedback for your team?

Get an understanding of how your candidate handles both successful and underperforming team members. If you need to, ask follow-up questions such as, “How do you like to share positive feedback with your team members?” and “Tell me about a time someone you managed wasn’t meeting goals.” Again, you want to see behavior that’s consistent with your organization’s values. If transparency is important to your organization, a good candidate may meet with team members regularly to discuss goals and key performance indicators, and offer public praise for a job well done.

Tell me about a time you [exhibited one of our core leadership values].

If you want to see a specific leadership value in your candidates, ask them about a time they exhibited it. If, for instance, you value employee development, ask the candidate to tell you about how they’ve encouraged learning and development on their past teams. If you value employees who speak their minds, ask the candidate to tell you about a time a team member disagreed with them and how they handled it. The trick to developing these leadership interview questions is to keep the criteria simple so the candidate can easily recall a related situation. If you said, for instance, “Tell me about a time you provided development opportunities for a remote team that wasn’t meeting goals,” many candidates would come up short. Instead, focus on one qualifying criterion at a time, such as “Tell me about a time your team wasn’t meeting goals” and layer on follow-up questions, such as “Did you offer development opportunities?” as needed.


While employees are often promoted to managers for their hard skills, truly great managers have soft leadership skills that set them apart from the rest. These are the people you want heading up your organization, and managing your team. Use these leadership interview questions to find the candidates that most closely align with your organizational values and culture to hire the best managers for your team.

For more interview interview questions and best practices, download our ebook, Top Interview Tips: The Employer’s Essential Handbook.