Questions to Ask in Your CSM Interview to Get Ahead of Product Issues

Great CSMs can't make up for bad product.

And no, that’s not your fault. I’ve been there.

You show up to work with all the enthusiasm in the world. You build strong relationships, run killer QBRs, and craft the kind of Success Plans that would make a strategist weep with joy.

But your product? Clunky. Confusing. Buggy.

Or worse — it just doesn’t deliver the value it promised.

And suddenly, all your charm, all your process, all your hustle… still ends in churn.

The Hard Truth: Product Is the # 1 Driver of Retention

Let’s say it louder for the people in the back: Great Customer Success Managers can’t make up for a broken product.

Not with a smile.Not with documentation.Not even with next-level hand-holding.

If your product can’t deliver outcomes, customers will leave. That’s the game.

So... How Do You Avoid This Trap?

If you’re interviewing for a Customer Success role, don’t just focus on preparing your answers.

Do some due diligence.

Because you’re not just taking a job — you’re signing up to represent the product.

If it’s not something you believe in (or at least feel confident can improve), you’re setting yourself up for burnout and frustration.

Here’s a checklist I’ve used myself — a mix of sleuthing and strategic questioning to get the real story before Day 1.

Before the Interview: Do Your Homework

1️⃣ Read G2 Reviews

This is the unfiltered customer voice. Look for recent reviews and recurring themes. Is there a consistent complaint? Are people raving about specific features (or lack thereof)? Context and timing matter — a 1-star rant from 2019 may no longer be relevant, but a flood of similar feedback from last quarter? That’s a red flag.

2️⃣ Check Community Chatter

Head to Reddit, Slack communities, LinkedIn groups — anywhere customers are talking. What are they saying? Are they fans? Frustrated? Fleeing?

3️⃣ Browse the Knowledge Base

Is it comprehensive, current, and user-friendly? Are there recent articles tied to product updates? This is a direct reflection of how the company supports its customers post-sale.

4️⃣ Look for Press Releases

Any recent product launches? Innovation announcements? Acquisitions? This shows whether the company is actively investing in its future — or just coasting.

5️⃣ Scan for Industry Awards

Recognition from trusted organizations for product excellence or innovation? That’s a good sign they’re not just relevant — they’re competitive.

During the Interview: Ask the Right Questions

1️⃣ Ask for a Product Demo

You’re going to be on the front lines supporting this tool. You should see it. Don’t be shy — this is a reasonable and insightful request.

2️⃣ Request a Trial (if possible)

If the company allows it, get hands-on. I once had to complete tasks in the product as part of the interview process — and honestly, it gave me way more confidence walking in.

3️⃣ Roadmap Reality Check

Ask: “What percentage of last year’s roadmap shipped?”This helps you separate aspiration from execution. A roadmap that’s just vibes doesn’t help you or your customers.

4️⃣ Understand the Feature Feedback Process

How does the company collect and prioritize customer feature requests? Is there a clear process, or do ideas vanish into the void? This tells you a lot about how much they listen to and value the customer voice.

TL;DR: Choose Wisely

You’re not just interviewing for a paycheck — you’re choosing the product you’ll be fighting for every day.

Make sure it’s a fight you can win.

Because if the product isn’t up to par, you’ll be working twice as hard… for half the results.

And no one — not even the best CSM on Earth — has time for that.

Have any product red flags you look for during interviews? Drop them in the comments or shoot me a message .