15 Important Questions for Executive-Level Interviews

As an executive search firm, we are constantly asking questions to help us connect the dots between an organization’s leadership needs and an individual’s leadership capabilities. The process of hiring to achieve the best possible outcome for every role begins long before the interview process.

Here are a few executive interview questions you need to ask yourself before you start talking to candidates:

1. Is my company crystal clear in its purpose and values, and who in my company will serve as the culture evaluator during the interview process?

2. Has the hiring manager collaborated with multiple stakeholders to establish a clear vision for the role and the image of what success looks like when the right person is added to the team? (Note: if you are still thinking of your hiring process as filling the open box near the top of the org chart using yesterday’s job description, you have work to do)

3. Do you know what the most important leadership traits look like for your company? Our clients have constantly asked us for Relentless Learners, People/Colleague Developers, and Results Drivers. Yours may be different, but these have consistently come up for us over the past 4 years.

Once you have clear answers to the questions above, you can begin your outreach and alignment process. Your goal when you get to an in-person interview stage is to spend time with as few, highly aligned candidates as possible. Your time is valuable. Their time is valuable. Make sure your initial screening process is so strong that only the best of the best make it to the in-person interview stage.

At Y Scouts, we focus on 3 main areas when interviewing C-suite and other senior level leaders:

1.) Purpose and Values
2.) Functional Expertise
3.) Exceptional Leadership Traits.

Below is a sampling of 15 executive interview questions and the logic behind each related to Purpose, Values and Leadership Trait discovery.

(Functional Expertise questions should be specific to the success outcomes you’ve defined in the Role Visioning Process)

1. If you were going to teach a college course, what course would you teach?
This question helps us understand the subjects the interviewee cares most deeply about, and also provides insight into where they feel their strengths lie.

2. What leader or leaders do you look up to and why?
This question helps us understand their leadership style. If the candidate is a huge fan of Jack Welch for example, and the company we represent has a collaborative culture, it’s a good data point that might suggest misalignment in culture and values.

3. What is one truth you believe in that most people disagree with you on?
This question helps us learn a lot about the candidate’s belief system and whether or not they are willing to challenge the status quo.

4. What’s one assumption people make about you that is dead wrong?
This question helps us understand if the candidate has a high degree of self-awareness. It’s a great indicator of emotional intelligence – does the person really know how they affect people around them.

5. Who is your mentor/s and what recent challenge/s have you sought their advice for?
This question helps determine if they have a ‘go-to’ person outside of their company. It highlights their need for help or counsel, which can be an indicator of a desire to learn and grow.

6. Tell me about a time when you had to make a tough business decision that supported your company’s purpose, but may have had a negative, short-term financial impact.
This question helps us get a sense of the leaders commitment to the mission or purpose of their previous company and how willing they are to make the hard decisions leaders have to make when faced with the trade-off of staying true to the company mission/purpose or deciding to pursue short-term interests.

7. Tell me about a time you broke a rule for an employee.
This question helps us understand the candidate’s people orientation. We specifically focus on employee handbook type rules, not safety, risk, or other rules that should never be broken. If they’ve never broken a rule for an employee, chances are they don’t deal well with ambiguity and look at the world very black & white.

8. If you could go back and give your 21-year old self a valuable piece of advice, what would you say?
This question helps us understand the depth of a candidate’s introspection and reflection ability.

9. As you think about your career, who is a team member you had a huge impact on and what are they doing today as a result of your leadership?
This question helps us understand if the candidate has a specific story about someone they coached/mentored/developed and the details of what that person is doing today. Specificity is the key here – details, and lots of them.

10. If you could work on solving any problem in the world, what one problem would it be?
This question provides insight into the difference in the world they want to make and perhaps an indicator of their true passion. Is it aligned to your company’s mission and purpose?

11. What is your leadership philosophy?
This question is intentionally vague. Most leaders will answer this question in a way that demonstrates their core values or the way in which they lead.

12. What’s the one mistake you’ve made in your career that you wish you could go back and fix?
If the candidate isn’t able to share a specific story, keep looking. Every leader has made a mistake.

13. Tell me about a contentious situation between colleagues you’ve had to resolve. Specifically, how did you work through the tension?
This question helps us understand the candidate’s approach to conflict resolution. Again, specifics matter.

14. What specific mental, physical, emotional and/or spiritual activities do you engage in to keep yourself operating at your optimum level?
This question reveals the candidate’s approach to their overall well-being.

15. What are you learning right now?
Every candidate should have at least one immediate answer to this question. If not, be afraid.

If you’re ready to supercharge your leadership search and get the right person in your organization, please contact us. If you’d like to share some of your favorite executive interview questions, we’d love to share them with our Leadership Community.

You may enjoy these executive level posts about interview questions:

// 15 High Level CTO Interview Questions
// 15 Exceptional CIO Interview Questions
// 15 Incredible CFO Interview Questions
// 15 Amazing CMO Interview Questions
// 15 Extraordinary COO Interview Questions

Y Scouts is an executive search firm that helps nonprofits and social enterprises find exceptional leaders. Contact us if you are looking to find an exceptional leader. To be considered for exceptional leadership opportunities with our clients, please take the first step by joining the Y Scouts Leadership Community.