CSMs don't need more playbooks. They need more reps

I recently wrapped up a workshop series with a CS team that was trying to do something hard.

Not hard like learning a new tool. Hard like rewiring how they show up in customer conversations.

We spent two sessions going deep on frameworks: how to ask better questions, how to listen, how to turn a routine check-in into something actually useful. Then I sent them out to practice what they learned. When they came back, what they shared was honest and specific and a lot more interesting than I expected.

Breakout session where the group practiced what we covered

Here's what stood out.

1. The silence is harder than the question

Everyone got comfortable asking the tough questions. "What does success look like for you?" "What's keeping you from getting more value?"

But then came the silence.

And almost every person in the room admitted their instinct was to fill it. Jump in. Rephrase. Answer it for them. One person said she literally doodles for six seconds just to keep herself from talking.

The silence is where the customer does the work. When you fill it, you steal that from them. You also usually end up putting words in their mouth that weren't actually there. The question is the easy part. Waiting is the skill.

2. Getting the reflection wrong is fine. It's actually useful.

One person shared something that stopped me. She reflected back what a customer said, got it half right, and the customer corrected her. In doing so, the customer gave her more information than she would have gotten if she'd nailed the reflection perfectly.

Think about that. The reflection isn't about being right. It's about showing you were listening and giving the customer a chance to confirm, correct, or expand. When they correct you, they lean in. That correction is often where the real insight lives. Don't be afraid to reflect imperfectly. It opens doors.

3. Curiosity beats expertise when a customer throws you a curveball

At some point, every CSM runs into the moment where a customer mentions a tool, a competitor, or a strategy they don't know anything about. The instinct is to answer anyway. Or deflect. Or worse, start explaining how your product compares to something you've never actually used.

The better move is simpler. Say you don't know and ask them to tell you. "I've heard of that but I'd love to understand how you're actually using it. What's it doing for you day to day?" That question does three things. It's honest. It's curious. And it usually gets you more useful competitive intelligence than any product briefing ever will. Customers who mention new tools often want to talk about them. Let them.

4. The pre-call is where joint calls are won or lost

The team brought this one up in the context of working with their sales counterparts on renewal and expansion calls. I've seen this go wrong more times than I can count. Two people from the same company join a call, both want different things, and the customer watches them figure that out in real time. It's a disaster.

Even a 10-minute alignment beforehand changes everything. Who's opening? What's the goal? Who handles what objection? What are we NOT going to bring up today? If you can't get the 10 minutes, send a message in Slack or Teams. Lay out the plan. Get agreement. It doesn't have to be formal. It just has to happen.

Showing up aligned is not a nice-to-have. It's basic professionalism, and customers notice when it's missing.

5. The product trainer mindset is a trap

This one came straight from the team, and they called it out themselves, which I respected. There's a version of CS where you're basically a really knowledgeable trainer. You teach people how to use the product. You answer questions. You run enablement sessions. And that's it. That version of CS does not drive retention or expansion. It definitely doesn't position you as a strategic partner.

The shift is uncomfortable because product knowledge is safe. Asking about business goals is not. You might hear something you don't want to hear. The customer might not have clear goals. They might be struggling in ways you can't fix with a feature tour. But that discomfort is the job.

The best CSMs I know are not the ones who know the product best. They're the ones who know their customers' businesses and have enough courage to ask the questions that matter. The teams I work with don't need more playbooks. They need reps. They need to practice being uncomfortable, listen to their own calls, and give each other honest feedback. That's the hard part. Playbooks just give you something to practice with.