Customer Success teams are wired to solve.
We jump into onboarding. We start talking about features. We assume what customers want based on use case or industry.
But here’s the hard truth: You can’t deliver value if you don’t understand the problem.
And most CSMs are operating with half the picture. Guessing at goals, assuming pain points, and missing what truly matters to the customer.
That’s where discovery comes in.
Discovery Isn’t a Phase. It’s a System.
In many CS teams, discovery is treated like a one-time task: Ask a few questions during kickoff, then move on.
But real discovery is ongoing. It’s the engine that powers the entire customer lifecycle.
When done well, it helps your team:
- Define what value truly means to this customer
- Align on expectations for 30/60/90-day outcomes
- Choose the right plays
- Spot risk before it shows up in usage metrics
- Drive strategic conversations that build trust
What Most Teams Miss
Too often, discovery gets stuck at the surface.
CSMs ask about use cases and features but stop there. They don’t push deeper. They don’t get specific. They don’t uncover the real “why” behind the customer’s decision.
Here’s how to go further:
- “What made you choose us over other options?”
- “What does success look like by the end of this quarter?”
- “If this doesn’t work, what happens on your side?”
- “Who needs to see results for this to be considered a win?”
These questions shift the conversation from features to outcomes. And that shift is where real value starts.
Tailor Discovery by Segment and Stage
Every account, segment, and lifecycle stage needs discovery tailored to it. You’re not asking the same things in onboarding vs. pre-renewal. A scaled SMB account won’t need the depth of a strategic enterprise account.
That’s why good discovery isn’t just a skill. It’s a team capability and it needs to be enabled, documented, and reinforced.
Discovery is Ongoing, Not One-Time
Your champion left? Start over. You’re entering the expansion phase? Rediscover. You’re prepping for a QBR? Revalidate assumptions.
Customer Success isn’t static. So your understanding of the customer can’t be either.
The best CSMs revisit discovery like a habit. They don’t assume. They confirm. And that’s how they stay ahead of risks, surface expansion opportunities, and maintain trust with stakeholders.
So What Does Good Discovery Actually Look Like?
It’s not just “asking more questions.” It’s asking the right ones, at the right time, for the right customer segment.
Here’s how to operationalize good discovery across your team:
1. Start Before Kickoff
Good discovery doesn’t start in onboarding. It starts before the handover:
- Sync with Sales to understand customer goals, value drivers, and decision criteria.
- Look at the deal notes. What pain were they solving when they signed?
2. Ask Tiered Questions
Train your team to go beyond surface-level:
- Use Case Questions “What are you planning to use the product for?”
- Value Questions “If this works, what changes in your day-to-day?”
- Risk Questions “What could block you from seeing success here?”
- Executive Alignment Questions “Whose success is this project tied to internally?”
Build a discovery flow that ladders up from tactical to strategic. Don’t jump straight into feature talk.
3. Make It a Team Habit
Discovery isn’t one-and-done. It needs to be ongoing:
- In QBR prep: “Have goals shifted?”
- After expansion: “What does value look like now?”
- When new stakeholders join: “What matters to them?”
Build checkpoints into your lifecycle journey where discovery is revisited, not assumed.
4. Document It in One Place
If insights live in scattered docs or Slack threads, they’re lost. Create a shared Success Plan or CRM field that captures:
- Business goals
- Success metrics
- Key stakeholders
- Known risks
- Desired outcomes per milestone
This becomes the source of truth for every engagement.
Discovery Powers Everything Else
When discovery is strong, here’s what happens:
- Success Plans become tailored and outcomes-driven
- Executive conversations feel consultative, not reactive
- Expansion becomes a natural outcome, not a forced upsell
- Risk is caught early before it becomes a churn conversation
It’s not some kind of secret sauce. It’s just great discovery, done consistently and intentionally.
Need Help Operationalizing This Across Your Team?
I work with CS leaders to build out:
- Discovery frameworks that go beyond kickoff
- Coaching programs that upskill teams on strategic conversations
- Success plan templates and value realization toolkits that stick
📅 Want to talk through how to embed this into your CS org?
👉 Book a free consultation call and let’s explore whether coaching or consulting is the right fit for your next stage of growth.