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Today’s Episode
Everyone thinks they know how to prepare for a PM interview until the interviewer baffles you with a trick question.
Today we have Gayle McDowell, the author of Cracking the PM Interview, and the architect behind hiring processes at top tech companies.
She breaks down exactly how to ace behavioral and case interviews.
What makes this episode different? We’re not just giving you generic advice…
We’re breaking down real answers, exposing the biggest mistakes, and showing you how to fix them.
By the end of this episode, I’m confident you’ll know why most candidates fail PM interviews and exactly what to do instead.
We cover:
How to Practice for Interviews - 00:01:41
The Correct Way to Answer Behavioral Questions - 00:15:16
How to Answer Tough Case Questions - 00:35:21
How to Land Interviews in 2025 - 00:56:59
Gayle’s Revenue Picture - 01:06:14
Key Takeaways
1. The Right Way to Prepare for PM Interviews
Most candidates take the wrong approach:
Scrambling through books/videos → Taking notes → Practicing answers in their heads.
And that’s why they struggle.
A real interview isn’t a script. Your interviewer will challenge you, interrupt you, and dig deeper…
And if you’ve only prepped solo, you won’t be able to adapt.
Instead, focus on what actually works:
A. Record yourself answering questions → catch timing issues and unclear explanations.
B. Do mock interviews with PMs → simulate real-time pressure.
C. Practice thinking on your feet → because structured problem-solving beats memorized answers.
Knowing the right answers isn’t enough; you need to train like it’s the real thing.
2. Why Most Candidates Fail Behavioral Interviews
Behavioral questions should be easy, right?
You’re just talking about yourself.
But most candidates mess them up because they don’t understand what interviewers are actually looking for.
What’s actually happening?
The interviewer is trying to decode your core strengths:
Are you a structured thinker?
Do you match the company’s values?
Can you adapt your experience to different contexts?
As an interviewee, your job is to shape your experience into an answer that actually fits what’s being asked.
3. The Right Way to Answer "Tell Me About Yourself"
Most people answer by either:
Listing their resume in reverse order.
Starting at the very beginning and rambling.
Both are less-effective approaches.
Instead, a structured, intentional approach is:
Start with who you are today ("I’m a PM at [Company], focused on [Area]")
Step back and walk through your career arc (highlighting only the most relevant roles).
Weave in what makes you uniquely suited for this role.
Even more important — anticipate the assumptions people will make about your background.
And use your intro to highlight your product thinking and leadership — the areas where people might have doubts.
4. How to Answer “What’s Your Biggest Weakness?” Without Ruining Your Chances
Picking these “fake” weaknesses is definitely going to backfire:
"I work too hard."
"I care too much."
What works is:
Choose a real weakness — "I can be too direct in communication, which sometimes causes friction."
Mitigation — "I’ve learned to slow down, add context, and check how my messages might come across."
Tell a short story — "Once, I sent a quick Slack message that came off harsher than I intended. It hurt a key relationship, so now I take an extra few seconds to soften my wording."
This works because it shows self-awareness and growth, which interviewers love.
5. Why You’re Failing Case Interviews (And How to Fix It)
Most PM candidates walk into case interviews thinking it’s about getting the right answer…
It’s not.
Because the interviewers aren't looking for a perfect solution.
They’re actually evaluating:
Can you structure a problem clearly?
Do you think about users first?
Can you relate everything to business outcomes?
Can you prioritize effectively under constraints?
So, don’t jump to solutions.
Instead, start by clarifying the problem, understanding the context, and asking the right questions.
Because if you’re not leading with questions, you’re already failing.
Where to Find Gayle
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Up Next
I hope you enjoyed the last episode, where I shared 11 key lessons from 50 podcast episodes and answered a bunch of your questions. Up next, we have episodes with:
Satish Mummareddy - L7 PM at Meta (Fmr)
Ethan Evans - Fmr VP, Amazon
Tal Raviv - Gen AI PM, Early Patreon, Riverside
Finally, check out my latest deep dive if you haven’t yet: The AI Job Search Tool Market: Everything You Need to Know
Cheers,
Aakash