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Sales Discovery Training: How to Ask Better Questions and Uncover Real Needs

Sales Training
by Chris Orlob
August 5, 2025

Most reps are sleepwalking through discovery. And it’s killing their close rates.

They rely on canned intros and generic BANT-style questions like:

  • “What are your goals?”
  • “What’s keeping you up at night?”

Sound familiar? These shallow prompts lead to one thing: surface-level conversations that miss the mark. 

The result? Reps pitch too early, miss buying signals, and sound like every other vendor flooding the buyer’s inbox.

Great discovery isn’t about gathering data. It’s about generating urgency. Real sales discovery training turns reps into deal accelerators, not question-askers.

Let’s break down how.

The Sales Discovery Process Most Teams Get Wrong

Your reps don’t need more scripts—they need stronger instincts. 

Because here’s the truth:

  • Most discovery calls are over-scripted and under-coached
  • Reps default to features instead of focusing on friction
  • They fail to connect pain with outcomes

The right sales discovery process flips that. It’s consultative, confident, and conversion-focused. It's what separates sellers who drive urgency from those who stall in "maybe."

What Elite Discovery Sounds Like (and Why It Closes)

Top sellers don’t interrogate. They diagnose.

Instead of jumping into product specs, they zero in on pain points, business drivers, and emotional triggers. This is where consultative selling shines. 

For example, data shows that top-performing reps spend less than 10% of their time in discovery talking about product features.

Key stat: Top AEs spend less than 10% of discovery talking about the product. That’s intentional. The rest is spent listening for urgency, friction, and hidden landmines.

Here’s what they’re tuned into:

  • Language that signals cost (time, money, efficiency)
  • Emotional cues like frustration or fear
  • Strategic shifts or upcoming deadlines

It’s not about having the right answers. It’s about asking the right questions—and knowing what to do with the answers you get.

Two Power Levers That Separate Top Reps

Sales discovery training isn’t about throwing more questions at reps—it’s about teaching them how to ask with purpose. These two levers will instantly tighten any discovery call.

1. Intent-Driven Questions

Forget fishing for facts. Great reps ask questions that create motion:

  • Instead of “What tools are you using?”, go with: 
    • “What’s breaking in your current workflow that’s forcing this change now?”

Every question should map back to urgency, timing, or influence.

2. Sequencing That Creates Urgency

If you're wondering how to create urgency in B2B sales, it's not about pressure. It's about progression. Start broad (“How are you handling this today?”), then narrow in (“What’s that costing you in time or output?”).

This sequence creates momentum—without sounding like a pitch.

Sales Discovery Techniques That Build Real Pipeline

These aren’t theoretical. These are the exact techniques reps should master to stop wasting discovery and start surfacing deals with real intent.

1. Challenge the Status Quo

Ask: “What’s changed that made this a priority now?”

This opens the urgency gap. If they’ve lived with the problem this long, why are they looking now? You’ll surface internal triggers (missed KPIs, leadership changes) or external drivers (budget cycles, competitor moves).

2. Surface Hidden Stakeholders

Ask: “Who else might have a strong point of view on this?”

B2B deals are a team sport. On average, 6–10 people influence a buying decision. These kinds of SaaS discovery questions uncover blockers early, like the security lead who derails you at the last minute or the VP who’s holding budget strings.

3. Translate Pain Into Metrics

Ask: “What’s this issue costing you right now—win rate, CSAT, ramp time?”

This is where discovery shifts from frustration to financial impact. Pain is emotional. But pain + impact? That’s budget-worthy.

4. Define Success Early

Ask: “What does a win look like after 30 days live?”

This snaps vague goals into concrete outcomes. Maybe they want adoption. Maybe visibility. Maybe measurable time savings. Either way, you’re aligning expectations while building a roadmap to value.

5. Use Negative Reverse Selling

Ask: “What might make you think this isn’t a fit?”

This is classic negative reverse selling—and it works. It flushes out silent objections and shows you’re not afraid of honest friction. Confidence builds credibility.

How to Reinforce Discovery Skills That Actually Stick

You can’t train discovery through decks. Great account executive training is rooted in live call coaching and behavior change—not theory.

Here’s how to make discovery skills permanent:

  • Use real call recordings: Show reps what great (and not-so-great) looks like across real scenarios. Highlight what moved the deal forward—and what didn’t.
  • Drive peer coaching: High-performing AEs don’t just compete—they collaborate. Create a culture where reps break down calls together and sharpen each other’s skills.
  • Track with tactical scorecards: Focus on what matters—did the rep tie pain to metrics? Did they identify urgency triggers? Are they using intent-driven follow-ups?

Discovery isn’t just a step in the process—it’s the step that shapes everything after.

Discovery in Action: A Call Breakdown

Let’s break down a discovery call from a mid-market AE at a SaaS company selling onboarding automation. No pitch deck. No demo. Just one conversation that flipped a stuck deal into a fast-track close.

What Was on the Surface

The CRM showed basic intent:

  • Inbound lead from a webinar
  • Head of Customer Success booked the call
  • No timeline, no budget, no clear pain

The rep could’ve treated this like another “curious, not serious” call. Instead, they got surgical.

What Got Unlocked on the Call

On paper, this looked like a soft lead. But with the right discovery moves, the rep turned a surface-level conversation into a strategic opportunity. Here’s what sharp questioning revealed—and why it changed the entire sales motion.

1. Hidden Pain That Wasn’t in the Brief

The buyer initially framed the issue as a “process efficiency” project. 

But by pressing with intent-driven questions like: “What’s breaking down when new customers onboard today?”, the AE uncovered a bigger issue—new accounts were taking 3x longer to onboard than promised, triggering churn within 60 days.

2. Budget Influence That Wasn’t in the CRM

Midway through the call, the buyer mentioned they were “trying to get RevOps and Finance to agree on prioritization.” 

Instead of moving on, the rep asked: “Who’s driving the prioritization conversation internally?”

That surfaced a RevOps lead who owned the tech stack budget. The AE had been selling to the wrong function.

3. Champion Alignment Before the Deck

Before the AE ever shared slides, they asked: “If this worked the way you need it to—what would that change for your team 30 days from now?” 

The buyer responded with specifics: “Fewer fire drills, cleaner handoffs, and a win in front of my VP.” 

Boom—emotional driver + internal validation goal = instant champion potential.

Why This Worked

This wasn’t magic. It was execution.

The rep followed a discovery framework built around:

  • Curiosity, not checklist questions
  • Pressure-testing the status quo
  • Tying pain to measurable impact
  • Mapping influence, early and often

This call turned a passive inbound into a multi-threaded opportunity with clear urgency—and it happened before a single slide was shown.

Want Faster Deals and Tighter Pipeline? Start With Discovery

Here’s the real talk: If your reps aren’t surfacing urgency in discovery, they’re clogging the pipeline with “maybe later” deals.

Sales discovery training is the fastest way to drive win rates, shorten cycles, and build trust from the first call.

If you’re ready to overhaul your team’s discovery game, start with a Discovery Audit from pclub.io. We’ll break down real calls, highlight missed opportunities, and show you exactly where reps can go deeper to close faster.

No guesswork. Just sharper conversations, stronger pipelines, and reps who know how to own the moment.

Book your Sales Team Audit now. Let’s unlock the deals hiding in your calls.

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