Despite decades of sales training and frameworks, we haven’t solved a key selling fundamental: Discovery is still broken. Too often, it’s rushed, shallow, and undifferentiated—leading to no decision, lost deals, and pricing pressure.
According to CSO Insights, 35% of lost deals are due to poor qualification and lack of buyer understanding. And 70% of opportunities still end in no decision, a stat that reflects the failure to articulate a compelling reason to change—not a failure of product.
To explore what’s driving these challenges—and how AI might offer a path forward—25 B2B leaders gathered in London for a lively panel and debate. What emerged was a clear-eyed view of the current sales discovery gap, the promise of AI, and the risks if we get it wrong.
The Discovery Gap Is Real—and Expensive
Discovery is supposed to uncover pain, build urgency, and set the stage for value. But in most B2B sales orgs, it’s a missed opportunity:
- 68% of buyers say reps don’t understand their business before pitching. (Gartner)
- Only 20% of opportunity records include customer metrics or quantified pain. (Genius Drive)
- And 35% of lost deals come down to poor qualification. (CSO Insights)
These stats reinforce a core truth: reps are struggling to uncover real pain and connect it to impact. They’re moving too fast, jumping to demos, and failing to build the “why change” story. Discovery is being treated like a checklist, not a conversation.
As one panelist shared, “The enemy of discovery is knowledge. The moment you believe you have all the answers, you stop asking the questions that matter.” — Tom Canning, Sales Consultant / CRO
The Five Biggest Sales Discovery Challenges
The event participants—ranging from CROs to Enablement and Revenue leaders—surfaced five recurring challenges:
- Discovery is too shallow or rushed – Reps often pounce on one pain point, then move to a demo. The result? No depth, no urgency, and no real impact uncovered.
- Insights don’t evolve into a value story – Even when discovery happens, the insights stay buried in call notes. There’s no structured path to turn them into a compelling business case.
- Reps lack personalization and context – Many AEs go in blind—no persona insights, no vertical context. This leaves buyers cold and makes every call feel generic.
- Information is fragmented and overwhelming – Sales assets, research, and messaging live in 10 places. Reps can’t find what they need, when they need it.
- Discovery isn’t treated as a continuous process – It’s often a single-step activity. Great teams, by contrast, embed discovery across the full sales cycle.
Where AI Can Actually Help
AI isn’t a silver bullet – but it can help fix these issues, if implemented thoughtfully. Here’s where it offers real promise:
- Crafting a confident point of view – Sellers can start with hypotheses informed by peer benchmarks, past wins, and firmographic data. AI helps sellers lead, not just listen.
- Persona-level personalization – AI can tailor talk tracks, questions, and proof points to the stakeholder’s role and industry—making conversations feel bespoke from the first minute.
- Generating high-quality discovery questions – Instead of repeating tired questions, AI can guide reps to ask layered, insightful questions that expose strategic pain.
- Auto-synthesizing prep – AI can assemble call briefs from CRM data, buyer news, and internal assets—saving reps hours in research.
- Evolving discovery into a living value story – As calls unfold, AI can capture key metrics, pain points, and outcomes—building a narrative that champions can re-tell internally.
As one leader put it: “Used well, AI clears the runway for curiosity.” It handles the admin work, so humans can focus on the “why.”
But Be Warned: AI Can Also Hurt Discovery
The panel didn’t shy away from the risks:
- Hallucinations and stale data undermine credibility – “You should assume the data generic LLMs give you isn’t accurate—the sums are not correct.” — Daniel Head, Jacquard
- Generic outputs make sellers sound the same – “You can spot an AI-written email a mile away. I’ve even seen reps sprinkle in typos to make it look human.” — Mike Slater, Carlyle Group
- Rushing to pitch – Reps get overconfident with AI-provided answers and skip the discovery process altogether.
Worse yet, if AI replaces soft skills like curiosity and active listening, it doesn’t elevate the seller – it just automates mediocrity.
What Great Discovery Looks Like
The vision painted by the panel wasn’t about automation—it was about amplification. The best discovery experiences feel like co-designing a business case.
As one panelist said, “Effective reps layer questions like a good therapist, and exchange proof points for every ask they make.”
When AI supports this—not shortcuts it—it can create smarter, more consistent discovery motions across teams.
The Bottom-Line: AI Can’t Replace Curiosity, But It Can Accelerate It
The takeaway from this session wasn’t to hand discovery over to the bots. It was to empower humans with better tools—so they can show up smarter, ask better questions, and tell stories that stick.
If B2B sellers want to win in a world of buyer skepticism and no-decisions, they’ll need more than good products. They’ll need great discovery—and AI, done right, might just be the assist we’ve been waiting for.
Check out the full briefing and attendee profiles from the event here:
https://cuvama.com/ai-in-sales-discovery-insights/
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