ABOUT 1 MONTH AGO • 4 MIN READ

How to ask the right questions to get ahead

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Product Career Newsletter

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Hello there Reader,

Most Product Managers get to the end of an interview and ask questions for one of two reasons.

They want to validate if they actually want to work there. Or they want to make themselves look smarter.

And here’s the thing… both approaches completely ignore the most important thing you need to know to land your next role faster.

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The problems with typical interview questions

Generic questions lead to fluff answers.

When you ask an interviewer what it’s like to work at the company, they’re speaking on behalf of the company in a very forward-facing way.

They’re not going to give you honest, candid feedback.

They’ll tell you what they think you want to hear.

I would never expect a hiring manager to be honest about just how awful working with the VP of Sales is. Or how often they have to build something because the HiPPO said so.

Asking the wrong questions wastes precious time.

When you ask a recruiter how the product team is structured, they likely aren’t in a position to answer that well.

You’re lucky if you get 5 minutes to get answers. That time is precious. Don’t waste it asking the wrong person the wrong question.

Company info won’t help you succeed.

Asking questions early on about the company structure or how they do goal-setting doesn’t actually help you prepare for later rounds.

It’s maybe interesting to learn, but these are details you can get later. If they even matter…most of the time they don’t.

Smart questions won’t change minds.

Thoughtful questions can reinforce you care about the right things. But if they were already a “No” on you, no question will change that.

If you bombed the case study, asking about their agile rituals won’t save you. And if you crushed it, you’re already going through.

The power balance isn’t in your favour yet.

At the start of the process, the company holds all the power. They’ve received hundreds of applications and are setting up calls with maybe two dozen candidates.

When you’re asking questions to validate this is a place you want to work, you’re showing a lack of awareness of where the power sits.

That balance shifts in your favour the later you get into the process.

What to do instead

Get information on the next interview.

This is the single most important thing to get first.

You want to know exactly what the format will be for the next round.

Who you’ll be meeting with.

What they really care about.

Some recruiters are great at detailing this out. Some companies even publish it on their website. But always double-check and get it in writing.

You should never jump on an interview call unsure about what to expect. If you’re unclear, chase that recruiter. It’s their job to help you.

Ask questions like:

“Should I expect to tell some stories about my experience in the next interview?”

Once you know what to expect, find out the most important signals that interviewer is looking for.

Try

“What are the three most critical skills or areas of expertise the hiring manager is looking for?”

This guides your preparation on which stories to tell.

If the hiring manager says their biggest challenge is “misalignment with stakeholders,” you can prepare to talk about how you’ve managed difficult stakeholders in the past.

Use outreach to get better signals.

You want authenticity from the person helping you validate if this place is right for you. You won’t get that from an interviewer.

You need to reach out to PMs who actually work at these companies. That’s where you’ll get the real picture.

Not only can you learn what it’s like on the inside, you can learn the problems the team really cares about. This is your insider’s advantage.

Too many people think about outreach solely as a way to get referrals. That’s narrow thinking.

Follow my 3x3 Framework for how to conduct that outreach.

Save the tough questions for the end.

Once the power balance has shifted in your favour, that’s when you’ll get the information you need to make a confident decision.

In the later stages, they don’t want to lose you. If something makes you feel uneasy, now’s the time to ask.

Found some bad Glassdoor reviews? The appropriate time to ask about them is near the end of the process.

The bottom line

Interviewing for Product Manager roles is a game. You need the right tactics to win.

Don’t waste your question time trying to look smart or validating the company before you are even close to getting an offer.

Use it to get information that will help you prepare and succeed in the next round. Rely on outreach to get more authentic insights into the company.

And you’ll be on your way to offers in no time.


Hey there, quick thing. I’ll be sending one more newsletter before ending 2025. I have tons more planned for next year.

If you’ve been getting value from this newsletter or anything else I share, can you take 1 minute and leave me a testimonial? It would mean the world to me.

Thank you, and wishing you a safe, happy holiday season.

Wishing you success,
James

James Gunaca

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