Win-Loss Insights
The Lost Art of Sales Discovery
What You’re Missing, What It’s Costing You, and How to Fix It
Thirdside research shows that 65% of lost deals stem from poor discovery. Most companies skip or rush discovery — and it’s costing them more than they realize. From lost deals to silent churn, here’s what you’re missing, how to spot it, and what to do about it.
Our research has shown that 65% of losses can be attributed — at least in part — to sales not doing enough discovery. And yet, in many organizations, discovery has become more of a checkbox than a craft.
If you’re losing deals — and you’re not sure why — it’s time to look closer. Some losses will be obvious, but many more will come with vague or misleading reasons in your CRM. Others won’t show up as traditional losses at all: they’ll die in the pipeline as ‘no decision,’ or go closed-won only to show signs of poor adoption, unmet expectations, and eventual churn at the first opportunity.
If any of that sounds familiar, the issue may not be your product, your pitch deck, or your price.
It might be your discovery process.
And let’s be honest — in many companies, there isn’t one. Not a real one. Not a structured, intentional, repeatable approach to uncovering what the customer actually needs, how they buy, and what will get in the way.
It’s the lost art of sales discovery. And it’s costing B2B companies millions.
The Hidden Cost of Skipping Discovery
Over the last 15 years, Thirdside has conducted hundreds of post-sale interviews with B2B buyers across tech, healthcare, education, and financial services. We’ve uncovered patterns and blindspots most companies miss — and one of the most persistent is poor or non-existent discovery.
Here’s what the data says:
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- In win-loss interviews where the deal was lost, 65% of buyers said sales did not do enough discovery.
- In churn interviews, a common refrain from former customers: “They never really understood our use case.”
- In “no decision” outcomes, discovery is often the root failure — buyers get overwhelmed, confused, or unconvinced.
- In win-loss interviews where the deal was lost, 65% of buyers said sales did not do enough discovery.
The impact is severe. Without proper discovery:
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- You demo the wrong things.
- You engage the wrong stakeholders.
- You miss the competitive context.
- You demo the wrong things.
You lose the deal — or worse, win it and lose the customer later.
What You Miss When You Skip Discovery
We’ve put together a quick visual below to show just how much information gets left behind when sales jumps into pitch mode too quickly:
| Missed in Discovery | Consequence |
| Key pain points | Product doesn’t feel relevant |
| Business context | Misaligned value proposition |
| Decision criteria | Proposal gets deprioritized |
| Internal politics | Your champion gets overruled |
| Competitive vendors | You don’t differentiate effectively |
| Timing and urgency | Deal stalls or goes to no decision |
| Technical limitations | Churn risk post-sale |
Symptoms of Shallow Discovery
Think discovery isn’t a problem for your team? Here are some red flags:
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- A high percentage of deals lost to ‘no decision.’
- Closed-won accounts that churn at the first renewal.
- Low product adoption despite high expectations.
- Demos that sound the same every time.
- Sales reps who talk more than they ask.
- CRM loss reasons defaulting to ‘price’ or ‘competition.’
These symptoms are common. But they’re only symptoms. The underlying cause often lies in the early stages of your sales process — when assumptions are made and questions are skipped.
You won’t know for sure unless you ask. That’s where Thirdside comes in.
We interview your buyers — wins, losses, no-decisions, and even churned customers — to reveal what really happened. And in many cases, it started with a missed discovery opportunity.
Real Stories, Real Consequences
The Generic Demo That Blew the Deal
One buyer told us, “It felt like they were demoing to a different company. We had specific pain points. They never asked.” The competitor, by contrast, spent the first meeting just listening — and then won the deal with a tailored proposal.
The Churn That Could Have Been Prevented
A churned customer explained, “We realized a few months in that the product wasn’t built for how we work. But we were too deep to back out. At the first renewal, we were gone.”
The 'No Decision' That Was Really a Hidden Objection
“They were great to talk to, but we couldn’t figure out how it would actually fit into our workflow. We liked them — but we paused. And they never followed up.”
All of these losses were preventable. But only if someone had taken the time to ask the right questions — early, and often
How to Bring Discovery Back
Here’s how to rebuild your discovery process — and make it a competitive advantage:
Structure It
Don’t leave discovery to chance. Develop a standardized approach:
- A shared discovery framework (e.g. MEDDIC, SPIN, SPICED, or your own)
- Required topics to cover before a demo is scheduled
Qualification beyond BANT — focus on fit and friction
Coach for It
Sales managers should review discovery calls, not just late-stage deal reviews. Are reps:
- Asking open-ended, high-impact questions?
- Digging into why now and why not?
Identifying potential blockers or technical gaps?
Reward It
Celebrate great discovery in your sales culture. Highlight reps who:
- Uncover unexpected insights
- Challenge assumptions
- Bring clarity to the buyer’s internal debate
Check It
Not sure how well your team is doing? Let us talk to your buyers. We’ll surface the discovery blindspots directly from the source.
Don’t build your revenue strategy on assumptions. Just ask.