How Revenue-Driven CSMs Use Discovery to Unlock Growth

Most expansion doesn’t fail because customers don’t want more.

It fails because Customer Success Managers don’t ask the right questions.

If expansion discovery sounds like this:

You’re already too late.

Those aren’t discovery questions.

They’re late-stage closing questions, asked without context, urgency, or business justification.

Revenue-driven CSMs know something different:

Expansion isn’t sold.

It’s discovered.

And the quality of that discovery determines whether expansion feels pushy… or inevitable.

The Core Mistake: Treating Expansion as an Event

One of the most common breakdowns I see in CS orgs is when discovery happens.

Most teams wait until:

And then try to talk about expansion.

By that point:

Sales teams would never run discovery this way.

Yet in CS, we often treat expansion as something you “bring up” instead of something you continuously uncover.

Revenue-driven CSMs flip that model.

They treat discovery as:

Not a checkbox before pricing.

Expansion Discovery ≠ Adoption Discovery

This is where many well-intentioned CSMs get stuck.

They do great adoption discovery:

This is important, but adoption alone does not create expansion.

Expansion comes from understanding how the customer’s business is evolving, not just how the product is being used.

To do that well, discovery has to operate at multiple levels.

The 3 Levels of Expansion Discovery

Level 1: Current State (The Table Stakes)

This is where most CSMs operate day-to-day.

Typical questions:

This helps you:

But on its own, it rarely creates new revenue.

Current state tells you what is.

Expansion lives in what’s changing.

Level 2: Business Change (Where Expansion Emerges)

This is the most underutilized layer of CS discovery, and the most important.

Revenue-driven CSMs are constantly asking:

Why this matters:

Expansion is rarely driven by:

It’s driven by:

Change creates new problems.

New problems create new value opportunities.

If you’re not actively discovering change, you’re relying on luck for expansion.

Level 3: Future Risk & Opportunity (Where Revenue Is Justified)

This is where revenue-driven CSMs separate themselves.

Instead of stopping at goals, they explore consequences.

Questions like:

This reframes the conversation from:

“Do you want more product?”

to

“What happens to the business if this doesn’t scale?”

Now expansion is no longer about features or seats.

It’s about protecting outcomes and unlocking upside.

That’s a CFO-level conversation.

The Most Important Shift: Don’t Jump to the Solution

One of the biggest sales lessons that applies directly to CS:

Discovery doesn’t create value unless it’s reflected back.

Too many CSMs hear a problem and immediately respond with:

Revenue-driven CSMs slow down.

They reflect the problem first:

Only after alignment do they introduce expansion as:

A logical response to a business problem

Not a sales motion

When done right, expansion feels obvious, not awkward.

The Strongest Expansion Signal Most Teams Miss

One of the most reliable expansion signals isn’t usage spikes or feature requests.

It’s this question from leadership:

“Can we do this everywhere?”

When a customer succeeds with:

And leadership starts thinking about scale, that’s not an upsell moment.

That’s a discovery moment.

The real questions become:

Expansion here isn’t about selling more licenses.

It’s about helping leadership solve a bigger version of the same problem.

Why Sales Discovery Skills Matter in Customer Success

Many CS teams shy away from sales discovery language.

But the reality is:

Sales teams are trained to:

Revenue-driven CS teams do the same

just after the deal is signed.

The best CSMs don’t “become salesy.”

They become strategic.

Your Challenge

In your next customer conversation, don’t ask about product needs.

Ask instead:

Listen for:

That’s where expansion lives.

Some Tactical ways to get started

Use these questions to move discovery beyond adoption and into business change, risk, and opportunity.

1. “What has changed in your business since we last connected?”

This is the single most important expansion question. Change creates new needs, and new budgets. Also, ALWAYS do your homework first. Use AI or just good old fashioned research to have a point of view on headwinds and tailwinds that they might be experiencing and incorporate that into the question. 

2. “What priorities are getting the most attention from leadership right now?”

Expansion often follows leadership pressure, not user demand.

3. “What’s becoming harder to manage as the team grows?”

Growth introduces friction. Friction creates justification for scale solutions.

4. “What goals feel most at risk this quarter?”

Risk-focused questions unlock urgency without being pushy.

5. “If this initiative stalls, what’s the downstream impact on the business?”

This shifts the conversation from product usage to business consequences.

6. “Who else in the organization is impacted if this doesn’t improve?”

Expansion almost always lives beyond the original buyer or team.

7. “What does success look like at the leadership level, not just for this team?”

This helps you connect team-level wins to executive outcomes.

8. “What happens when this approach needs to scale across more teams or regions?”

This naturally surfaces multi-team, multi-role, or enterprise expansion paths.

9. “What would ‘great’ look like six months from now if this problem were solved?”

Vision-based discovery creates pull toward expansion instead of push.

10. “What’s the cost of doing nothing or keeping things the same?”

This is where expansion becomes a business decision, not a product decision.

How to Use These

Expansion shouldn’t feel like a pitch.

It should feel like the logical next step.

How are you struggling to dive in deeper with discovery? Reply with a comment anytime I can help you out. 

Onwards,

Mark