Most discovery calls sound like a bad first date - one side interrogates, the other side checks their watch. That’s not selling, that’s scaring people. Great discovery doesn’t feel like a Q&A session; it feels like a real conversation where the prospect actually opens up.

If your current playbook is just a list of “qualifying questions,” toss it. Here’s how to ask smarter, softer questions that uncover real problems without sounding like a pushy rep.

SALES

Most discovery calls sound like an interrogation - forcing prospects to shut down or give short answers. The best salespeople know how to ask questions that feel natural, uncover real pain, and open the door to executive-level conversations.

Here’s a 7-question framework you can use to do just that:

Start simple. After setting your agenda, ask: “I’m guessing you don’t take every call that comes your way. What made you take this one today?”

If they share a problem, great - go deeper. If they don’t, move to Question 2.

When they shrug it off, push gently: “Sure, I know I called you, but my guess is you don’t take every call. What caught your ear?”

This often uncovers an operational problem you can dig into.

If they give a neutral answer like “We track renewals in spreadsheets,” make it easier to answer by offering options: “Got it - when folks track renewals that way, it’s usually because they’re struggling to manage existing contracts or control new spend. Which is it for you?”

Multiple-choice questions show expertise and make the conversation flow.

If they say what they want (“We need a better way to track renewals”), ask why: “Is that because you’ve auto-renewed something you didn’t want, missed negotiation windows, or just trying to prevent that?”

This uncovers the deeper problem behind their request.

Stories reveal the real executive pain. Ask: “When did you realize this became a problem? Was it a missed renewal, over-purchasing licenses, or just a gut feeling?”

The answer gives you context - and a reason this problem matters to leadership.

Impact questions often feel too aggressive. So soften them: “Would fixing renewals make a real dent in getting spend down, or is it more of a nice-to-have and there’s a bigger initiative at play?”

This lets prospects clarify priorities without feeling pressured.

When asking about executive-level impact, acknowledge the awkwardness: “I know this might sound like a tough question, but is this an isolated incident… or something that’s happening over and over and blowing up budgets?”

This keeps the conversation comfortable while surfacing business-level risk.

Bottom Line: These questions feel conversational - not salesy - yet they lead you straight to operational problems, executive concerns, and business impact. Master them, and you’ll turn every discovery call into a real business conversation.

HEADLINES

→ My 10-step process for nailing prospecting on LinkedIn, according to AMP's CEO

SOFTWARE

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Team B2B Whales