Buyers arrive researched, and AI has cut comparison shopping to minutes. Open with ’what do you want to get out of this call?’ and go deeper, not longer.
Key takeaways
David sat through 20 minutes of decade-old qualification questions when he only wanted technical answers. One question would have unlocked the call: “What do you want to get out of today?”
Assume research. Buyers put your URL into a language model and get competitors, reviews, and pricing scraped from Reddit even if you hide it. Discovery has to extend their thinking, not repeat it.
Replace “why” with trigger verbs. Describe, explain, walk me through.
If your qualification set has no past-based question, fix it today. “Walk me through the last time you did this” reveals blockers, process, and the future decision path in one answer.
Cap the list at about five questions and leave room to drill down and actually listen.
Two bookends: open with “what motivated you to reach out?” and close with “to make this worth your while, what else do you need to see?”
I’m sorry, but I don’t believe in your whys. I feel like I’m being interrogated. I get my back up. I get defensive.
Regan Barker, co-founder, Ricavi
If you look at your qualification and you don’t ask them something about the past, go back and change it. Now.
Regan Barker, co-founder, Ricavi
What’s changed about the buyer on the other end of the call?
They’ve already done the work. Regan Barker cites research that nearly 60 percent of a buyer’s time in a purchase goes to independent research, and David Fastuca describes what that looks like now. He compared two fitness wearables by handing a model both product pages and asking it to check pricing, reviews, and Reddit. Two minutes. He’d have spent an hour. Any buyer evaluating a sales platform can do the same, including finding pricing a vendor thought was hidden.
So when a seller opens with “if nothing changes in six months, where will you be?”, an experienced buyer recognises the framework and mentally files the seller under salesperson. David lived it on a recent call with a well-regarded vendor. The questions were fine a decade ago. They weren’t what he needed.
What should the questions do now?
Extend the buyer’s thinking beyond what they’ve researched. Regan’s discipline is to swap out the accusatory “why” for verbs that give permission to explain, and to overlay curiosity on the checklist. The aim is the moment where the buyer says “I hadn’t thought of that.” A comparison table can’t produce that. A question about how this purchase will ripple through their organisation can.
The one question category most frameworks skip entirely is the past. Ask how they bought something like this before and you’ll hear the blockers, the missing stakeholders, and the budget failure. They’re telling you how the next decision will go.
How do you avoid asking too many questions?
Don’t bring a shopping list. Regan keeps about five prepared questions, listens properly to the answers, and drills down where the thread leads. A single open question, “walk me through how you target an account,” does more work than ten closed ones. The buyer reveals the customer relationship management (CRM) system, the process, and the bit they hate, without being asked. David’s two favourites bookend the call. The opener, credited to Luigi Prestinenzi, asks what motivated them to reach out. The closer asks what else they need to see. That one has turned 30-minute meetings into an hour.
Questions this episode answers
How has AI changed discovery calls?
Buyers arrive already informed on pricing, competitors, and reviews. Discovery has to start from their research and add what they haven’t considered, rather than re-running basics they’ve already answered for themselves.
How many questions should you ask in a discovery call?
Around five prepared questions, with room for follow-ups and real listening. Depth beats coverage, and over-questioning is something the asker usually feels happening.
What are the two most important discovery questions?
Open with “what motivated you to reach out today?” Close with “to make this worth your while, what else do you need to see?” The first sets the agenda in the buyer’s words. The second exposes what they’re weighing.
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