If you were a doctor diagnosing a patient, you wouldn’t prescribe medicine after asking just one question about symptoms, would you? The more questions you ask, the clearer the diagnosis becomes.
That’s exactly how good discovery works in sales.
And the truth is that across my 15 years in sales, roughly 95% of opportunities are won and lost in the discovery stage.
Not in your pitch deck. Not in your demo. Not in your pricing negotiations. Discovery.
The Real Job of Discovery
Let me be direct: your job in discovery isn’t to talk about your product. It’s to be incredibly curious.
Most people think being good at sales means you have the gift of the gab. They couldn’t be more wrong. The best salespeople I know follow an 80/20 rule – they listen 80% of the time and talk only 20% of the time.
When done right, discovery is your secret weapon.
It’s hands down the most powerful tool you have for closing more opportunities. But here’s what most founders miss: discovery isn’t a one-and-done conversation at the start of your sales process. It’s an ongoing dialogue that continues throughout the entire journey.
Why Early Discovery Is Your Golden Opportunity
Think about it this way: prospects are most open to sharing information at the beginning of your process. Once they’ve seen your demo or received pricing, they become more guarded. They’re less likely to connect you with other stakeholders or share sensitive information. That’s why front-loading your discovery is crucial.
But here’s what makes great discovery truly powerful: when you do it well, you actually don’t have to “sell” anything.
Instead, you’re simply guiding someone through a process where choosing your product becomes a no-brainer. You’ve uncovered so much pain and mapped your solution so perfectly to their needs that the sale almost makes itself.
Why Discovery Never Really Ends
Here’s something that most founders get wrong: they treat discovery like a one-and-done meeting. But in reality, things change throughout the sales process. New stakeholders join the conversation. Priorities shift. Requirements evolve. This is why you need to stay constantly curious.
I like to think of my role in discovery is like channel my inner five-year-old. Yes, I’m serious. Five-year-olds are naturally curious and aren’t afraid to ask “why” about everything. They’re not worried about looking stupid – they just want to understand.
Let me give you a practical example: When a prospect says, “Send me an email with that information,” most founders would just say “okay” and send it. But if you’re doing discovery right, you’re going to dig deeper:
- “Who else needs to see this information?”
- “What specific parts are most important to include?”
A real use case I saw recently looked like this. The company was selling an expense management solution. Their prospect might be perfectly content with their current process of manually collecting receipts. But by asking deeper questions, you might uncover that:
- Their finance team is spending 15 hours a week processing expenses
- They’re regularly missing reimbursement deadlines
- They have no visibility into spending patterns
- They’re unable to forecast cash flow accurately
- Their growth is actually being constrained by their manual processes
Now you’re not selling expense management software – you’re selling them their time back, better employee satisfaction, and the ability to scale their business.
Structuring Your Discovery for Success
Here’s how I advise founders to segment their first discovery call. Think about it in four distinct buckets:
- Company-wide objectives for the year
- Business unit-specific challenges and goals
- Personal motivations of your contact
- Technical sales qualification questions
For each segment, prepare specific questions in advance. Think of it like a tree where each question is a trunk, and your follow-up questions are the branches. This structure helps ensure you don’t miss crucial information while keeping the conversation flowing naturally.
The Basics That Make or Break Your Discovery
I’m a big believer in getting the basics right in sales. Being prepared, being on time, and being professional are non-negotiables. And a key part of that is having an agenda for every meeting. To be honest, I simply won’t ever have a meeting without an agenda. It’s a waste of everyone’s time. My tried-and-tested format to setting an agenda is:
- Start with introductions
- Explain that you’ll be asking questions about their company
- Promise a high-level overview of your solution
- Outline clear next steps
- Ask if there’s anything specific they want to add to the agenda
This last point is golden because it creates a value exchange. You’re going to ask them questions, but you’re also committing to addressing their specific interests.
Common Mistakes That Kill Opportunities
I see the same mistakes over and over again with founders:
- Not asking enough questions
- Rushing to demo
- Leading with slide decks in the first meeting
- Failing to uncover real pain
- Selling solutions instead of solving problems
- Not having a prepared question framework
Remember this: if you want to speed up your sales cycle, you need to slow down at the beginning. Investing time in your discovery process will make everything else easier.
How to use the information you discover
After you’ve put time into understanding your prospect’s needs and pain points – what you do next is key.
First, show that you’ve actually listened. Summarise the key points and specific challenges they’re looking to address, and the outcomes they hope to achieve.
Say something like “Based on our discussion, it sounds like your top priorities are reducing churn and driving faster time-to-value. Does that align with what you shared?” Getting that confirmation shows you were paying close attention.
Then, pivot to how your product can address those priorities. “Great, I’m excited to show you how our solution can help improve those areas. In our demo, I’ll walk through features tailored to your needs.” Make sure to reference the exact pain points they outlined – that demonstrates you listened intently and are committed to delivering value.
The follow-up is vital too. Your next touchpoint should reiterate those key points from the discovery. “Just wanted to recap our discussion – I know you’re focused on boosting efficiency and cutting churn. In our demo, I’ll highlight how our platform can move the needle on those fronts.”
Brining it back to their challenges shows you truly understand their business.
Throughout the process, keep those discovery insights top-of-mind. Refer back to them, show how your solution addresses them, and make it clear you’re committed to helping them succeed. That’s what makes prospects feel heard and confident you’re the right partner.
The Bottom Line Impact
Let me be crystal clear about what good discovery means for your business:
- Faster sales cycles
- Higher contract values
- Better product-market fit
- More closed deals
- Less capital needed to scale
Here’s the thing about closing: when founders come to me asking for help with closing more deals, it’s never actually a closing problem. It’s always a discovery problem.
Get discovery right, and closing happens naturally.
I’ve seen countless startups transform their sales performance simply by improving their discovery process. It’s not about being more aggressive or pushy – it’s about being more curious and thorough. When you truly understand your prospect’s pain points and challenges, the solution becomes obvious to both parties.
Remember: prospects don’t care about your product. They care about their problems.
Your job in discovery is to help them articulate those problems clearly, understand their full impact, and see how your solution can transform their business. Do that well, and everything else falls into place.
Author: Matthew Codd
I’m Matthew, I have 15 years of commercial leadership experience, helping VC-backed B2B technology companies scale revenue and transition from founder-led sales.
I use my experience to help early-stage start-ups with GTM expertise, sales best practice, and hiring insights.
I co-founded Cosmic Partners in 2022. We are SaaS sales recruitment specialists for VC backed B2B tech companies.
