Let’s talk about discovery.

We’ve spent years teaching CSMs to ask better questions.

Understand your customer’s goals.
Uncover their pain points.
Listen more carefully.
Be curious.
Ask follow-up questions.

All good advice.

But I think we’re missing a much bigger piece of the equation.

The best CSMs don’t just ask better questions. They bring better perspectives.

Think about how a great management consultant operates.

They don’t walk into a meeting with a client and start by asking, “So, what’s going on in your business?”

They’ve done their homework.

They understand the industry. They’ve researched the competitive landscape. They understand the company’s business model, recent developments, strategic priorities, and potential challenges.

They come to the table with observations, insights, and hypotheses.

They have a point of view.

And then they use the conversation to validate what they’re seeing, challenge assumptions, and help the client think differently.

Why shouldn’t we expect the same from our CSMs?

I believe this is one of the biggest opportunities for Customer Success to evolve from account management into true strategic partnership.

Here’s something I see happen all the time.

A CSM prepares for a customer meeting by reviewing:

This is important. You absolutely need to understand what’s happening inside your accounts.

But here’s the problem.

You’re only looking at half the picture.

What about what’s happening outside the account?

What’s happening in their industry?

What’s happening with their competitors?

What’s happening inside their company?

What new pressures are their executives facing?

What changes in the market might fundamentally impact their priorities?

These are the things that can dramatically change the customer’s needs, expectations, and perception of value.

Yet most CSMs spend very little time researching them.

I think we need to start looking at customer discovery through three different lenses.

I believe there are three layers of intelligence every CSM should develop.

This is where most CSMs spend their time today.

Understand the account.

This is the foundation.

But understanding what’s happening inside the account doesn’t necessarily tell you why it’s happening.

For that, you need to look beyond the account.

This is where CSMs can start to differentiate themselves.

You should understand the bigger picture of the organization you’re supporting.

For example:

Think about how these developments could impact your customer relationship.

A new CRO might introduce an entirely different sales strategy.

A company experiencing layoffs might suddenly be under pressure to consolidate technology and demonstrate ROI.

An acquisition might create an opportunity to expand your solution across multiple business units.

A company moving upmarket might have entirely different enablement, onboarding, and operational requirements.

These aren’t just company announcements. They’re potential triggers for new customer problems, risks, and opportunities.

The best CSMs connect the dots before the customer has to explain them.

This is the layer I think most CSMs overlook.

You shouldn’t just understand your customer’s company. You should understand the industry they’re operating in.

What are the major trends?

What pressures are their competitors facing?

What is changing in the market?

What challenges are other companies in their industry trying to solve?

For example:

If you’re working with a SaaS company:

If you’re working with a financial services company:

If you’re working with a healthcare organization:

Now imagine walking into a customer meeting with some of this knowledge.

Instead of asking:

“How are things going with adoption?”

You might say:

“I’ve been following some of the changes happening across the SaaS industry. There’s a lot of pressure right now to improve sales productivity without increasing headcount. I’m curious whether you’re seeing similar pressure internally and how that’s changing your priorities for the sales organization.”

That’s a completely different conversation.

You’re not just asking about your product.

You’re demonstrating that you understand their world.

Here’s where I think we can take this one step further.

Understanding your customer’s account, company, and industry is important.

But the real value comes from connecting those observations to a hypothesis.

A hypothesis is simply an informed point of view about what’s happening inside your customer’s business.

It’s not an assumption you defend. It’s something you bring into the conversation to test, validate, or disprove.

Let’s look at an example.

Imagine you’re working with a mid-market SaaS company.

You notice three things:

Now connect those observations.

Your hypothesis:

The company may be preparing to scale its sales organization while simultaneously improving productivity and efficiency.

That creates a much better starting point for discovery.

Instead of walking into the meeting and asking what’s new, you might say:

“I noticed the recent CRO hire and the expansion into new markets. I’m curious how those changes are impacting your revenue organization. Are you looking at changing your sales processes or investing in new ways to improve productivity as you scale?”

Now you’ve opened up a strategic conversation.

You might discover that:

Suddenly, you have a much deeper understanding of what’s happening.

And potentially, an opportunity to help solve a problem the customer hasn’t even connected to your solution yet.

That’s what great discovery looks like.

I would encourage every CSM to start using a simple five-step process before their next strategic customer conversation.

Look beyond your CRM.

Spend 15–20 minutes researching the customer.

Look at:

You’re looking for things that might impact their business.

Take what you’ve observed and ask yourself:

Come up with two or three hypotheses.

You don’t need to be right. You need to have a thoughtful starting point.

Bring your observations into the conversation.

Don’t pretend you know everything.

Instead, share what you’re seeing and ask questions.

For example:

“I noticed your company has been investing heavily in AI. I’m curious how that’s impacting your team’s priorities and whether you’re evaluating changes to your current processes.”

Let the customer validate or challenge your thinking.

Now connect what you’re learning to business outcomes.

How does this impact their goals?

What processes might need to change?

Where could your solution help?

What additional problems are emerging?

This is where you move from understanding the business to helping improve it.

Discovery without action is just an interesting conversation.

Take what you’ve learned and turn it into something meaningful.

Maybe it’s a new recommendation, an executive discussion, a change in strategy, an adoption initiative, or an expansion opportunity.

The goal is to help the customer move forward.

There’s another reason I think this skill is going to become increasingly important.

AI is dramatically lowering the cost of research and preparation.

Historically, asking a CSM to research 20 different companies, monitor industry trends, track executive changes, and prepare strategic insights for every meeting was unrealistic.

Today, that’s becoming much more achievable.

Imagine having an AI workflow that prepares a briefing before every strategic customer meeting.

It could analyze:

And then produce:

1. What has changed?

Five meaningful developments since your last conversation.

2. What might be happening?

Three potential business challenges or changing priorities.

3. What should I investigate?

Five recommended discovery questions based on the research.

4. Where might we help?

Potential opportunities to improve business outcomes, mitigate risk, or expand the relationship.

Think about the advantage this creates for a CSM managing 20 or 30 accounts.

But here’s the important distinction.

AI can help you gather intelligence, identify patterns, and develop hypotheses.

The CSM still needs the business acumen to understand what matters, the judgment to challenge the hypothesis, and the curiosity to have the conversation.

AI can help you prepare for the conversation. You still have to create the value within it.

I think we’re at an interesting point in the evolution of Customer Success.

For years, we’ve focused on teaching CSMs how to manage relationships, drive adoption, understand customer goals, and ask better questions.

All of that matters.

But I believe the next evolution requires something more.

We need CSMs who understand business.

People who follow industry trends.

People who understand how companies make money.

People who can connect market developments to customer challenges.

People who can walk into a meeting with a perspective that challenges the customer’s thinking and helps them see something they might have missed.

That’s a different level of value.

And it’s how we move away from being viewed as another vendor or account manager and become a trusted business partner.

Before your next strategic customer meeting, don’t just review your CRM and prepare your agenda.

Spend 20 minutes researching the customer’s business.

Look at their industry.

Look at what’s changing inside their company.

Think about the challenges their leadership team might be facing.

Develop two or three hypotheses.

Then bring those perspectives into the conversation.

You might be wrong about some of them. That’s okay.

The goal isn’t to pretend you know more about their business than they do.

The goal is to demonstrate that you’ve invested enough time to understand their world and that you’re bringing something valuable to the table.

Your customer shouldn’t have to spend the first 20 minutes of every meeting educating you about their business.

They should feel like they’re talking to someone who has done their homework, understands their challenges, and has a point of view.

That’s the difference between managing an account and becoming a strategic business partner.

And I believe that’s where the future of Customer Success is headed.

Questions/Thoughts? Reply to these emails anytime 🙂

Onwards,
Mark