5 Interview Mistakes That Cost You Great Product Leaders—And How to Fix Them

Fireside Product Management

Content provided by Tom Leung. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Tom Leung or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

8M ago 30:48

MP3•Episode home

Hiring a Great Product Leader Is Harder Than You Think

Team, we’re back on the Fireside PM podcast, and today, I want to talk about a topic that keeps coming up: why even experienced executives struggle to hire strong product leaders. If you’re a CEO or CPO at a mid-to-late-stage company and you need to hire a killer Director or VP of Product, this post is for you.

You go through the hiring process, extend an offer to someone who looks amazing on paper—only to realize months later that it’s not working out. Sound familiar?

The good news? Most hiring failures happen because of a handful of predictable mistakes. Let’s break them down, one by one, so you can avoid them next time.

Mistake #1: Trying to Prove How Smart You Are

Executives sometimes treat interviews as a stage to showcase their own expertise. Instead of assessing candidates effectively, they dominate the conversation with industry insights or theoretical debates.

"We had one hiring manager who spent most of the interview explaining his product strategy instead of evaluating the candidate’s thinking. It turned into a monologue."

How to fix it: Think of interviews as a collaborative exploration, not a quiz show. Instead of trying to stump candidates with trick questions, create space for them to showcase how they think and solve problems. Ask open-ended questions like, ‘How would you approach building X in our business?’ and let them take the lead.

For candidates: If an interviewer starts flexing their knowledge too much, try steering the conversation back to your experiences by asking, ‘That’s really interesting—here’s how I’ve tackled something similar. How do you think that approach would work here?’

Mistake #2: Accepting Surface-Level Answers

Great PMs don’t just recite frameworks—they demonstrate depth in their thinking. But too many hiring processes settle for polished, rehearsed answers rather than pushing for real insights.

"We hired a candidate who sounded great in the interview, but once they were on the job, we realized they couldn’t actually navigate ambiguity."

How to fix it: Don’t stop at the first answer. Dig deeper:

* What was challenging about that situation?

* Why was it challenging?

* What did you learn, and what would you do differently?

Look for signals of intellectual honesty and self-awareness.

For candidates: Expect follow-ups. Instead of giving a generic “here’s what I did” response, add layers of reflection: ‘Here’s what I did, what was difficult about it, what I learned, and how I’d refine it next time.’

Mistake #3: Not Testing for True Product Sense

There’s a big difference between a good PM and a great one. Good PMs can apply best practices and tweak existing products. Great PMs spot breakthrough opportunities that others miss.

"We realized too late that the person we hired was great at incremental improvements but struggled to think big."

How to fix it: Give candidates real-world problems and see how they think. Ask:

* How would you improve X feature in our product?

* What’s an underserved user need in our market?

* How would you prioritize trade-offs between short-term execution and long-term vision?

The best candidates don’t just apply frameworks—they generate novel insights that connect market needs, user behavior, and technical possibilities.

For candidates: Show that you can think beyond standard playbooks. When discussing past work, highlight moments where you spotted opportunities others missed.

Mistake #4: Failing to Provide Real-Time Feedback

A lot of hiring managers expect candidates to read their minds. But vague questions and unclear expectations lead to wasted interviews and misjudged candidates.

"We almost passed on a great candidate because they started out with rambling answers. But once we gave them direct feedback, they nailed it."

How to fix it: Give candidates real-time guidance:

* If a candidate is being too verbose, gently ask them to summarize in two minutes.

* If they misunderstand a question, clarify what you’re looking for.

* If they struggle with structure, let them know you’d like a more formatted response.

The goal is to assess a candidate’s ability to learn and adjust, not just their ability to perform under perfect conditions.

For candidates: If an interview feels unclear, ask for guidance: ‘Would you like a structured breakdown, or a high-level approach?’ Adapt based on their response.

Mistake #5: Forgetting That You’re Being Interviewed Too

The best PMs have options. If your interview process feels adversarial, disorganized, or uninspiring, top candidates will walk.

"We lost a great candidate because they said our process felt chaotic and that we weren’t aligned on what we wanted."

How to fix it:

* Be respectful of their time. Don’t drag out the process with endless rounds.

* Showcase your team culture. Let candidates meet potential colleagues in a way that feels engaging, not like a test.

* Sell the role. Top candidates need to know why this is an exciting opportunity for them.

For candidates: If a company treats you poorly during interviews, that’s a preview of how they’ll treat you on the job. Pay attention to red flags.

Final Thoughts: Hiring Great PM Leaders Takes More Than Luck

The best product leaders don’t just fall into your lap—you have to create a hiring process that identifies them effectively. Avoid these five mistakes, and you’ll:

* Attract stronger candidates.

* Get a clearer picture of their real capabilities.

* Increase your offer acceptance rate.

* Build a world-class PM team that drives results.

If you’re a CEO or CPO looking to make a high-impact product hire, or if you want expert guidance on hiring strategy or need help with a can’t miss search campaign, I offer product management consulting and contingent searches where I personally vet all candidates at paloaltofoundry.com.

Thanks. Now get back to work :-)

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit firesidepm.substack.com

108 episodes

#Tech #MBA #Business #Tom Leung #Productdevelopment #Productmanagement #Productivity

5 Interview Mistakes That Cost You Great Product Leaders—And How to Fix Them

Fireside Product Management

14 subscribers

published 8M ago