What to ask when interviewing with an executive
We’ve heard all the questions from interview websites, and they're not setting you apart. Here’s how to ask questions that really stand out.
👋Hi, it’s Greg and Taylor. Welcome to our newsletter on everything you wish your CEO told you about how to get ahead.
Taylor and I have interviewed over 15 candidates in the past two weeks alone. Not one has asked us a question about Section’s product market fit.
This is surprising and disappointing for two reasons. First, Taylor and I are the final stage in the interview process – the “go / no go” on hiring. Good, strategic questions could set a candidate apart and be the deciding factor.
Second, any candidate should want to know this information before joining the company. A new job is an investment like anything else, and they’re not doing due diligence.
If you’re on the job market, we get it – you’re doing a lot of interviews, and you’re probably optimizing for getting hired, not finding the perfect role. But if you get to the executive interview round, your questions for the exec are JUST as important as your answers. If not more.
Here’s how to ask questions that signal you’re a great candidate – and examples of questions we wish we were asked.
– Greg
Why the executive interview matters more than you think
If you make it deep into an interview process for a mid-level or senior role, you’ll likely end up with a 30 minute exec interview.
Execs usually aren’t the hiring manager, but they can be just as influential in the process. They’re probably your hiring manager’s boss (or their boss’s boss), and they’re also often the tie-breaking vote if the team has several good candidates – which is the reality in today’s job market.
You get half an hour with them, and they’re coming in without much context on you. They’re likely coming from another call, and pulling up your LinkedIn as they join the Zoom.
So you should treat this interview differently than your other interviews. Assume you’ll spend more time asking questions than answering them. We both try to strike a 50-50 balance (15 minutes to ask you questions, 15 minutes for you to ask us), but some execs will kick off with, “Okay, what do you want to ask me?”
The exec isn’t just there to help you learn about the company or the role. They’re evaluating you based on the questions you ask. So you need to ask good ones.
What makes a great question
Executives want to hire people that can think strategically about the business, and then tie this back to the job they are interviewing for. A good question for an executive is high-low. It shows that you’re evaluating the business’s strategy and is specific enough to avoid the obvious.
Great executive interview questions have 5 key components:
They ask about the company, not the role – Your prior interviews are role-focused. Use this one to show that you’re strategic enough to evaluate the business and ask questions about how it’s performing – like product market fit, business challenges, differentiators, and strategy.
They ask about longer time horizons – Executives think 12-24 months in the future. So when you ask about specific parts of the strategy, frame the question around these time intervals.
They demonstrate business acumen – Executives want to hire people who understand how businesses operate and make money. So instead of asking “what’s your business model?”, ask “you’ve moved to a membership model, but I know this comes with a decline in conversion rates in favor of higher customer lifetime value. What indicators are you looking for to understand whether this model is working?”
They’re specific – Vague questions beget vague answers. And they make us feel like you don’t really care about the answer, you’re just moving through a list.
They indicate you’ve done your research – Reference what you’ve learned in previous interviews, on Glassdoor, or the company website. You can also reference what you’ve learned in past companies or roles that are relevant to this one. This gives us a glimpse into your experience and strategic thinking.
On the flip side, 80% of bad questions usually meet one of these two criteria:
They’re too open-ended – Do CEOs love to wax poetic about their companies? Sure. But questions like “what keeps you up at night?” are a waste of time in an interview.
They’re better suited for the hiring manager – Not only are we less-qualified to answer questions about team structure and success in the role, asking this indicates you’re only evaluating the role, not the company – not a very strategic mindset.
What to ask and not to ask
Here are some examples of questions you should stop asking executives and what kinds of questions you should ask instead.
❌ Bad question: “What’s your vision for the company?”
✅ Good question: “What do you think the most important moat for the company will be in the next 1-2 years?”
💡 What it does well: Asking about moats demonstrates business acumen and shows you understand that differentiation is key to a startup’s success – plus the question covers an exec-level time horizon.
❌ Bad question: “What’s the culture like?”
✅ Good question: “I don’t see any operating principles on your website, but I know startups tend to have them. What are the 1-2 behaviors that are your non-negotiables for success at company X?”
💡What it does well: Shows you understand how startups operate and that you’ve done your research. Plus, operating principles are relevant to executives – things like team dynamics less so.
❌ Bad question: “What does success look like in the role?”
✅ Good question: “What are the top metrics or indicators you’re tracking to assess product-market fit?”
💡What it does well: Presumably a hiring manager already laid out expectations for the role, and it’s not the executives job to tell you how to meet them. Instead, ask which metrics you’ll be expected to contribute to so that you can define success in the role.
❌ Bad question: “What keeps you up at night?”
✅ Good question: What’s the one thing that an outsider wouldn’t know about your business that drives its success or is limiting its growth?
💡What it does well: It’s a more specific way to get at what might be under the hood, and shows you know that businesses often aren’t as they appear on the outside.
❌ Bad question: What’s your exit strategy?
✅ Good question: Is there one competitor you want to beat within 12 months?
💡What it does well: It shows you care about winning (and that’s often the subtext of a question about exit strategy). But for CEOs, exits aren’t the end game – winning or dominating the category is. So ask about that.
A final tip: Remember that all team members, but especially fellow executives, talk to each other. So if you’re meeting with multiple execs, don’t recycle your questions. Or if you do, make it clear why you’re asking twice (e.g. “I already asked Greg this, but I’m curious to hear your perspective as COO)”.
Our advice
First of all, don’t treat this post as another listicle to source interview questions from – we’re not saying “these are the exact questions you should ask”. The point is to put real thought behind your questions and use them as a chance to get information – not just to try to stand out to an exec.
Case in point, the top search result for “questions to ask in an interview with the CEO” advises you to start with the number one question we advised against – the CEO’s vision for the company. So don’t copy/paste.
You’re likely not getting many executive interviews – make them a priority. Keep your answers to the exec’s questions tight so you have more time to ask your own. This kind of time management gives you control of the interview and makes a better impression.
Even if you don’t get this job, you might get a call in 6-9 months when one opens up that you’re a better fit for – Greg’s done it before. So make this 30 minutes count.
To the next 10 years,
Greg & Taylor
Great tips. Also, curious to know if others never heard the “moat” reference before?