The discovery call question that kills trust

Key takeaways

• Buyers judge you by your questions. The question set is your positioning, and it lands you in one of two boxes: salesperson or consultant.

• Avoid “why” openers. “Why did you choose that vendor?” reads as “you did your job badly.” “Describe what was happening when you chose that vendor” opens the same territory without the sting.

• Around 80 percent of seller questions are about today, according to Paul Cherry’s Questions That Sell, cited on the episode. People buy tomorrow, based on what happened in the past. Ask more past questions.

• First-time buyers and repeat buyers need different plays. One early question sorts them: “Is buying something like this familiar for you, or quite new?”

• Discovery never stops. Every meeting updates the problem statement, and each buyer on the committee may read that statement differently.

• Ask how others will read your documents. “When the chief financial officer (CFO) sees this, how will he interpret it?” stopped a champion mid-sentence and led to a redesign that got finance onside.

Winners actually ask less. It’s about going deeper on a set of questions rather than it becoming an interrogation.

Luigi Prestinenzi, co-founder, Ricavi

’Where are you on this journey?’ It doesn’t open a door. It opens a floodgate.

Regan Barker, co-founder, Ricavi

Why do discovery calls feel like interrogations?

Because the seller is working through a list instead of following a thread. Luigi Prestinenzi puts it plainly: every question either creates a barrier or opens the conversation, and buyers decide which category you belong in based on the questions you ask. A closed question at the wrong moment, or a why-question at almost any moment, pushes the relationship into tension. And when relationship tension is high, nobody moves into the zone of trust.

Regan Barker admits she gets her back up the instant someone asks her a why-question about data. It feels like being told her work isn’t good enough. That reaction isn’t unusual. It’s the default.

What should you ask instead?

Add a trigger verb. “Describe.” “Illustrate.” “Walk me through.” The question covers the same ground, but the buyer hears an invitation to explain rather than a demand to justify. Then overlay time. Past questions reveal how this buyer has made decisions before, who was involved, and what went wrong. Current questions establish the state of play. Future questions surface what success looks like. Most sellers live almost entirely in the middle bucket.

The past matters most for one practical reason. A buyer who has bought this category before knows their own procurement process. A buyer who hasn’t, or whose company was just acquired and now buys through a new parent, doesn’t. Luigi’s champion of six years hit exactly that wall. The right question turned it into a joint action plan instead of a stalled deal.

How do questions help the buyer sell internally?

By asking about the people who aren’t on the call. Luigi reviewed a discovery brief with a champion and asked how the CFO would interpret it. The champion hadn’t considered it. They rebuilt the problem statement together so the CFO would read it as a reason to say yes. That’s the consultative move in one question, and it comes from curiosity, not a script.

Questions this episode answers

Why are “why” questions bad in a discovery call?

They sound accusatory. Buyers hear a challenge to their past decisions, get defensive, and stop sharing. The same question rephrased with “describe” or “walk me through” gets the information without the tension.

What is the past, current, future question structure?

A way of balancing discovery so you’re not stuck in the present. Past questions reveal how the buyer decides. Current questions establish the state of play. Future questions define success. Most sellers over-weight the middle.

How many questions should you ask in discovery?

Fewer than you think. The hosts’ experience is that winners ask less and go deeper. A handful of prepared questions with room for follow-ups beats a checklist every time.