Customer Success loves to talk about empathy.

And while, understanding your customer’s perspective matters there are much more important skills that we need to develop. 

I think too many people have over-indexed on empathy.

Empathy helps you understand what your customer tells you.

Curiosity helps you discover what they haven’t told you yet.

And that distinction matters.

The best CSMs I’ve worked with aren’t necessarily the ones who are the most empathetic.

They’re the ones who are relentlessly curious. They don’t just accept the answer. They dig deeper. They ask another question.

They connect seemingly unrelated pieces of information.

And most importantly, they are genuinely interested in understanding how their customer’s business works.

That’s what turns a CSM from a relationship manager into a business partner.

Think about the typical customer conversation.

CSM:
“How are things going?”

Customer:
“Pretty good.”

CSM:
“Great. Are you getting value from the platform?”

Customer:
“Yeah, the team is using it.”

CSM:
“Awesome. Anything you need from us?”

Customer:
“Not really.”

And then the CSM updates the health score:

Green.

This type of conversation should be banned from every CSM call 

It doesn’t teach us anything.

And that’s the problem.

A CSM who is simply trying to make sure the customer is happy will often get surface-level answers.

A curious CSM is trying to understand what is actually happening inside the business.

Instead of: “How are things going?”

Try: “What’s changed in the business since we last talked?”

Instead of: “Are you seeing value?”

Try: “What is your team doing differently today that they weren’t doing six months ago?”

Instead of: “Are people using the product?”

Try: “Where are you seeing the strongest adoption, and where are you still struggling?”

Instead of: “Everything looks good. Anything you need?”

Try: “What’s the biggest problem your team is dealing with right now?”

These questions aren’t necessarily more complicated.

They’re just more curious.

And they create a completely different conversation.

One of the simplest ways I’ve learned to identify a great CSM is to listen to what happens after the customer answers a question.

A mediocre conversation looks like this:

Customer:
“We’re struggling with adoption.”

CSM:
“Okay. We can schedule some additional training.”

Conversation over.

A curious CSM asks:

“What do you think is causing the adoption problem?”

Customer:

“Honestly, managers aren’t reinforcing the process.”

The CSM asks:

“Why aren’t they reinforcing it?”

Customer:

“They don’t really believe it’s important.”

Now you’ve uncovered something completely different.

The problem isn’t adoption.

The problem is manager alignment.

And that leads to another question:

“Why don’t they believe it’s important?”

Now you’re getting closer to the actual business problem.

This is where great discovery happens.

Not because the CSM had the perfect question.

Because they were curious enough to keep going.

I think there are seven areas every CSM should constantly be curious about.

What’s happening in the company?

Your customer’s business is changing constantly.

Your understanding of it should change too.

What’s happening with the people involved?

A champion who was incredibly important six months ago may no longer be the person making the decision.

Curious CSMs notice.

How is the customer actually operating?

Don’t just understand how they use your product.

Understand the workflow around it.

Ask:

“Walk me through what happens from the moment this problem occurs until your team solves it.”

You’ll often discover opportunities that never appear in product usage data.

What’s improving? What’s getting worse?

This is where CS needs to move beyond activity metrics.

Don’t just ask: “Are users logging in?”

Ask: “What business metric are you trying to improve?”

Then: “How is that metric trending?”

And eventually: “What role do you think we’re playing in that?”

That’s a much more valuable conversation.

What’s different?

This might be the most powerful category of all.

Because change creates opportunity.

Ask: “What’s changed since we started working together?”

Maybe the company doubled in size.

Maybe the CRO left.

Maybe they launched a new product.

Maybe the sales organization was reorganized.

Maybe budgets were cut.

Maybe they’re moving upmarket.

Every meaningful change can create either risk or opportunity.

What could prevent them from achieving the outcome?

Curious CSMs don’t just look for reasons to mark an account green.

They actively search for reasons they might be wrong.

Ask: “What could derail this?”

Or: “What are we not talking about that could become a problem?”

Or one of my favorites: “If we were having a very different conversation six months from now, what would have happened?”

Those questions can surface problems long before a health score changes.

And finally: What’s possible that the customer hasn’t considered yet?

This is where curiosity becomes an expansion engine.

Don’t ask: “Do you need more seats?”

Ask: “Where else in the organization is this problem showing up?”

Don’t ask: “Would you be interested in another product?”

Ask: “What other problems are you trying to solve that are related to this?”

That’s the difference between selling more and discovering more.

There’s another important distinction.

Great CSMs don’t need to walk into every meeting with the answer.

They need to walk in with better questions.

That’s particularly important as AI changes the role of Customer Success.

AI can summarize meetings.

It can identify risks.

It can analyze usage.

It can surface trends.

It can even suggest questions.

But the CSM still has to decide:

Which question should I ask next?

And then listen carefully enough to recognize that the customer’s answer just changed the direction of the conversation.

That’s the human part.

AI can help you prepare for the conversation.

Curiosity determines the quality of the conversation.

There’s a deeper reason this matters.

The goal of Customer Success isn’t to make customers feel like they’re being taken care of.

It’s to help them achieve something valuable.

And you can’t help a customer achieve an outcome you don’t understand.

You can’t identify risk you haven’t discovered.

You can’t find expansion opportunities you haven’t uncovered.

And you can’t become a strategic partner if you’re only reacting to the information the customer volunteers.

That’s why curiosity matters so much.

Curiosity creates discovery.

Discovery creates insight.

Insight creates action.

Action creates outcomes.

And outcomes create the Profit Loop.

The next time you’re on a customer call, listen to yourself.

How many questions are you asking just to get information?

And how many are designed to actually understand what’s happening?

When your customer gives you an answer, don’t immediately move to the next question on your list.

Pause.

Think.

Then ask: “Tell me more about that.”

Or: “Why do you think that’s happening?”

Or simply: “What changed?”

You might be surprised by what you uncover.

Because empathy helps you meet your customer where they are.

Curiosity helps you discover where they need to go.

And that’s where great Customer Success begins.