How to Interview a Product Leader
Or: Are they a builder, a boss, or a project manager in disguise?
This is the second post in the How to CEO series—a collection of tactical, no-nonsense guides for running a high-growth company. If you’re just joining us, start with the series welcome post for the full roadmap, or check out How to Write a Job Description for a Senior Exec, the first post in the series.
Hiring a Head of Product is one of the most confusing interviews a CEO will ever lead—especially the first time. The resumes all look the same. The titles are all over the place. And worse: you’re often not even sure what kind of product leader you need. Are you looking for someone to build the vision? Ship what’s already on the roadmap? Or clean up a messy team dynamic?
Product leaders don’t work in a vacuum. The great ones show up ready to engage with your strategy, your customers, and your team—before the first roadmap is even written.
Your product leader should already feel like a partner in the business
before they walk in the door.”
There are three key axes that define how a product leader works—and you need to know where your candidate lands on each one before you make the hire.
Builder vs. Refiner
Not everyone can build from scratch. Not everyone wants to. And that’s fine—as long as you know which one you need right now.
Builders are zero-to-one thinkers. They see opportunity in ambiguity, ask “why not,” and are energized by figuring it out. You want a builder when you don’t yet have product-market fit, are entering a new space, or need to define something from the ground up.
Refiners make what’s already there better. They tighten processes, ship cleaner product, and focus on efficiency, clarity, and iteration. You want a refiner when the direction is clear and the focus is delivery, scaling, or optimization.
The mistake: hiring a refiner when you need a visionary—or vice versa. You don’t want someone perfecting a product that isn’t working yet.
Operator vs. Innovator
This is bigger than “product vs. project.” It’s about whether your product leader is just managing throughput—or driving new thinking.
Operators keep the system working. They build teams, run rituals, track metrics, and bring predictability to delivery. They’re often excellent in complex orgs where coordination and clarity are essential.
Innovators challenge assumptions. They work upstream. They partner with you on what to build and why—not just when and how. They see around corners and take smart risks.
The mistake: mistaking an innovator’s ambiguity for disorganization—or expecting an operator to create a strategy from scratch.
Business Strategist vs. Product Craftsman
This one’s subtle—and where I’ve seen the some CEOs screw it up.
Craftsmen love great product. They obsess over flows, friction, polish, delight. And that’s good. But the best ones tie that work directly to business outcomes—retention, expansion, differentiation.
Strategists start with the business problem. They ask: what do our customers need to succeed—and how does that success power our success? They talk to Sales. They know how the company makes money. They understand that “delight” without conversion or retention is just aesthetic.
The mistake: hiring someone who builds beautiful things that don’t move the needle. Or worse, things that make your customers happy—but don’t keep them paying.
You don’t need someone who’s perfect across all three axes. You need someone whose default mode matches where your company actually is. And the only way to figure that out is to ask better questions.
The 5 Questions That Reveal Who They Really Are
1. “What questions do you have for me about our business?”
I’m looking for the questions you’d ask as if you were already the Head of Product here. What are you curious about? What have you already observed or assumed about our strategy, our customers, our challenges?
You’re not just making polite conversation. You’re testing for curiosity, preparation, and thinking. Did they form hypotheses before showing up? Or are they waiting to be spoon-fed information?
Red flag: “I didn’t want to make assumptions.” That sounds humble—but it’s usually a cover for weak prep or weak instincts.
2. “Tell me about a product you built or led. Walk me through the business problem, the strategy, the challenges, the wins, the losses, and the results.”
Be specific. What were the trade-offs? What do you wish you’d done differently? What results did it drive?
You’re listening for real-world experience, not just good storytelling. Do they own the hard parts? Can they talk about metrics, impact, and regret with equal clarity?
Red flag: All features, no outcomes.
3. “Tell me about a product you admire—ideally close to our space. What do you think makes it great? What does it teach you about strategy, trade-offs, or execution?”
What’s one thing that product gets right that we could apply here?
This reveals pattern recognition, curiosity, and whether they’re learning from the world around them. You’re looking for someone who dissects greatness—not just uses it.
Red flag: “I just love the design.” Cool, but… so what?
4. “Tell me about a time you drove a product forward through cross-functional work. What relationships made it successful—or not? What did you learn?”
Walk me through the actual situation—who was involved, where was the tension, how did you move it forward?
Great product leaders don’t live inside product. They live between product, engineering, sales, marketing, and customers. You’re looking for someone who knows how to get the messy stuff done—without hiding behind process.
Red flag: “I just kept everyone on the same page.” That’s not a story. That’s a sentence.
5. “Let’s talk about you for a minute…”
Ask these four to get the full picture:
a. What’s your long-term ambition?
b. What’s your superpower—what do people rely on you for?
c. What’s something you’re still working on—or not great at?
d. If I spoke to your last manager, what would they say your biggest growth area is?
You want to understand how they’re wired, how they grow, and whether they’re reflective enough to be coached and trusted at the highest level.
Red flag: “I care too much” or “I work too hard.” Nope. Be real.
Final Gut Check:
Would I trust this person to own the product, the team, and the learning—right next to me every day?
Head of Product Interview Scorecard
Want a version you can actually use in interviews?
👉 Grab the Product Leader Interview Scorecard template here
(Click “Make a copy” to add it to your own drive.)
The CEO Move
Hire the product leader you want next to you every day, solving the same problem you care about most.
Not someone who’s just great at product. Someone who’s great at building this product, this way, with you. If you’re not aligned on what the company is here to do, it won’t matter how good they are.
“The hardest thing isn’t finding someone great—it’s finding someone great who wants to solve your problem.”
If this post helped you—or made you think of someone—please forward it to them. And let me know what resonated or missed. I read every reply.
#leadership #howtoceo #executivehiring #productmanagement #RealTalk