Top Interview Questions To Ask Senior Executives
Key Takeaways at a Glance:
Asking thoughtful, tailored questions in senior leadership interviews is every bit as important as giving strong answers.
Your questions signal what you value, how you think, and whether you’ll be a good fit for the role. It’s not just about your experience, but also your expectations, goals, and soft skills.
Generic or AI-generated questions often fall flat — the most effective questions are grounded in your personal experiences and interests.
Red flags in executive interviews include vague, rehearsed, or even evasive answers. Use your questions wisely to assess the company (just like they’re using their questions to evaluate you).
In executive interviews, asking the right questions to senior leadership is often just as important as answering theirs. In conversations with senior leaders, the questions you ask give you the chance to demonstrate your leadership abilities and get a feel for the company’s culture. And, ultimately, their answers can help you decide whether the position is a good fit for you.
Interviews with senior executives and hiring managers are two-way evaluations, not one-way interrogations. If you’re truly the best potential candidate for the job, you’ll treat it that way. It’s about more than just selling yourself — the best executive interview questions are the ones that lead to a genuine dialogue.
After all, you need to know what you’re getting into with this position, just like the leadership team needs to decide if hiring you is a step in the right direction. Preparing specific leadership interview questions creates an environment that’s productive for everyone. Both you and the management team can assess whether you’re the best candidate for the role — it’s always better to know now than later!
Why Asking the Right Questions Is Just as Important as Answering Them
The interview process with senior management is about learning what kind of environment you’d be stepping into if you got the job. Sure, it’s also about proving your value to an extent, but it’s vital that you take advantage of this opportunity to learn as much about the organization as possible.
You need to understand their management style and expectations just as much as they need to understand your skill set and leadership qualities. Everyone benefits when there’s alignment between your goals and those of the broader organization.
Asking the right executive interview questions can help you…
Clarify the specifics of the job description beyond what’s on paper
Understand the company’s vision and long-term strategy
Gauge the cultural fit and whether it would be a positive change for you
Build relationships and rapport with key decision-makers
Signal that you’re a budding business leader, not just a job seeker
Don’t pass up on this opportunity! Asking in-depth, thoughtful questions to learn as much as possible about the interviewer and their organization is one of the most important things you can do in an interview.
Why Your Questions Matter: What Senior Leaders Want to Hear
Consider this all-too-common scenario: A senior manager wraps up their pitch and asks, “Do you have any questions for me?” The candidate replies with, “No, I think I’m good.” That’s a big red flag, waving right in the leadership team’s faces.
Effective leaders can learn just as much about you from your questions as they can from your answers. What you ask about shows what you care about, and how you ask your questions reveals information about your soft skills and general thought process.
When candidates ask curious, genuine, direct questions, it demonstrates their intellectual engagement and emotional intelligence. Don’t just go with softball questions either — ask the specific questions you really want the answers to. Dig into the details and show that you can discuss meaningful topics with tact and professionalism.
The Strategic Value of Asking Questions
Let’s get tactical for a minute. Here’s what asking the right questions actually demonstrates to your interviewer:
Critical Thinking: You’ve gone beyond your basic interview preparation and research, showcasing your effective communication skills and leadership experience.
Alignment With Core Values: You understand that shared values aren’t the same as identical opinions. In other words, this is not to be confused with simply agreeing with everything your interviewer says!
Short- and Long-Term Vision: You can align expectations and reality, and you understand that you can’t know everything up front. You’re ready, willing, and able to help today, but you’re also keeping an eye on the future.
Relationship-Building: You’re able to develop rapport and find common ground, setting the foundation to work hand-in-hand with business leaders and other staff members.
Again, it’s impossible to know everything about a company from one executive interview. That said, mismatched expectations are among the biggest challenges for any new hire. If you want to avoid disappointment, don’t make assumptions — ask great questions to get good answers and form clear expectations.
Questions You Can Ask Senior Leaders in Your Interview
Before we discuss the details, here’s a quick disclaimer: These basic question templates are best viewed as starting points. The best interview questions are the ones that feel natural to you and are based on personal experience. Canned questions from Google or ChatGPT are too obvious, and a good interviewer can spot them a mile away. They’ll truly engage with you when your questions are clear, thoughtful, and relevant.
You can always get ideas from AI tools and then tailor them for content and delivery, but use your own words!
Questions About Leadership Styles
ChatGPT version: “Do you have any examples of tough decisions or major changes you’ve driven?”
Real-life version: “Do you have a recent, specific example of a tough decision you’ve made, and what factors drove you to that choice?”
This seemingly minor reframing invites your interviewer to respond with a story, not a soundbite. These narratives can provide insight into what type of leader they are and help you determine if there’s a strong cultural fit.
ChatGPT version: “How do you keep team members and leadership aligned on broader goals?”
Real-life version: “We all have our annual goals and milestones — how well would you say your team actually sticks to them?”
The latter version of the question encourages the interviewer to get deeper than the basic framework of their leadership style and address its real-world effectiveness.
Additional question options:
“Who’s on the leadership team? Did they all arrive at the same time, or have some been here longer than others?”
“How do you best process information? Do you prefer to read, hear, see, or discuss things?”
Questions About Expectations
ChatGPT version: “What can someone in this role do to showcase their value and express their ambitions?”
Real-life version: “Let’s say that I get this role and knock it out of the park. What would my future career path look like?” …or…
“I want this job. I know I can do well. If/when I become a top performer, what would my next potential steps be?”
The former version of this question is essentially just asking the interviewer to repeat the information listed in the job description. The latter version requires deeper thought into your long-term prospects if you get the job.
ChatGPT version: “How do you prefer to receive feedback? Is there open communication or a clear chain of command?”
Real-life version: “From this conversation, it sounds like feedback is a two-way street at this company, which is great. How does feedback from employees typically go to leadership? Is there an open door?”
The second version of this question indicates that you’ve been paying attention to the flow of conversation in the interview and thinking critically about what that means for you as a prospective team member.
Questions About Company Culture and Vision
ChatGPT version: “What’s your vision for the company over the next several years?”
Real-life version: “If everything went your way for the next 18 months, where would the company be?”
This is another tweak that might seem minor on the surface, but the adjustment in phrasing makes it more specific and tailored to the interviewer’s personal priorities and outlook.
Additional question option:
“How does senior management support professional growth for emerging leaders?”
Questions That Indicate Your Strategic Value
ChatGPT version: “What’s the biggest challenge facing the company right now, and how can someone in this role help?”
Real-life version: “You’ve mentioned that XYZ is the most significant challenge facing the company. Can I share my ideas to help overcome it?”
The real-life version of this question positions you as a problem-solver. You’re offering solutions for the next steps to take, instead of asking what those solutions might look like.
Additional question option:
“What types of new ideas or innovations would you be most excited about?”
Questions That Reveal Behavioral Tendencies
ChatGPT version: “Can you describe how the leadership team communicates with rank-and-file employees?”
Real-life version: “How does leadership communicate bad news or failures to the broader organization?”
The first version gives the interviewer an opportunity to cop out with a too-simple response. For instance, they might discuss the communication app the company uses or focus on how they communicate success (which is always easier than communicating failure). You can learn a lot about someone based on how they deliver bad news.
Additional question option:
“What accomplishments in your current management role are you most proud of?”
Best Practices for Crafting Your Interview Questions
If you want to stand out as the ideal candidate, here are some best practices for creating your own list of leadership questions.
Prepare a few confident, open-ended questions. Bring at least 3-5 questions that you can adapt to the flow of conversation. And don’t forget to think about follow-up questions!
Tailor your questions to the role you’re applying for (and your present position). Tie your questions to personal experience and accomplishments in your previous positions. If the interviewer mentions a product launch and you have project management experience, ask something about launch success metrics or stakeholder alignment to indicate that you know what you’re talking about.
Read body language during responses. If a question makes someone visibly uncomfortable or even evasive, take note of this potential red flag. (More on red flags in the next section!)
Avoid asking cookie-cutter, surface-level questions. Stuff like “What’s the dress code?” or “How much PTO do I get?” might be entirely valid questions, but they’re more appropriate for human resources, not a company leader.
Red Flags in Interviews With Leadership
Senior leaders can sniff out a bad fit in an interview, and so can you. Here are some potential red flags to look out for:
Evasive, unclear responses to your questions, especially those about culture and values. Just like a good interviewer can spot generic questions a mile away, you should be on the lookout for vague responses that sound more like sample answers than actual replies. Great leaders won’t dance around legit questions.
Overly rehearsed talking points that feel disconnected from your actual question. This can be an indicator that the interviewer is treating the interview process more like an interrogation than a conversation.
Dismissiveness around important employee concerns like work-life balance or pathways for advancement. These shouldn’t be difficult questions to answer — if they struggle to form a response, it might mean they don’t really care about the answers.
You’re looking for legitimately valuable insights, not empty platitudes. If there isn’t an honest, two-way dialogue during the hiring process, it’s often a sign of deeper issues within the organization.
Don’t Just Impress — Assess!
Interviews with senior executives are a two-way mirror. The questions you ask in your interview can accomplish the following goals:
Demonstrate your readiness for a leadership role
Show that you have the right skills for strategic thinking
Determine if this company will help you advance your career and become a good leader
Help you avoid surprises the next time you apply for a new position
Don’t settle for asking a series of common questions that don’t really tell you anything. The best way to approach your interview with senior leadership is to ask in-depth questions that reveal alignment on important issues, spark genuine discussions, and help both sides determine whether this is a good fit.
Need Help Preparing for Your Next Executive Interview?
Are you interviewing for a leadership position and want to stand out from a sea of executive candidates? Do you want help crafting a candidate’s approach specifically tailored to your leadership skills and career experience? Let’s talk.
Whether you’re looking for entry-level roles or an executive search firm, I can help you navigate every step of the interview process with confidence and clarity. Schedule a free discovery call with me today to discuss real-world strategies and actionable insights for your next executive interview!
About The Author
Emily Sander is a C-suite executive turned leadership coach. Her corporate career spanned Fortune 500 companies and scrappy start-ups. She is an ICF-certified leadership coach and the author of two books, An Insider’s Perspective on the Chief of Staff and Hacking Executive Leadership.
Emily works with early to senior executives to step into effective leadership with one-on-one coaching. Go here to read her story from seasoned executive to knowledgeable coach.