$340K was hiding behind a surface-level answer

"I don't think you're going to be ready to buy."

That's what a seller I recently coached said—out loud—to a prospect on a discovery call. I got the email about it last week, and it was a literal fist pump moment.

Here's what happened.

He'd been working this deal for a while. The CIO was his point of contact, and the conversations had been... fine. The process was crawling along, a little pain and some mild frustrations—but nothing substantial. It was the kind of deal that lingers in your pipeline without ever really moving forward.

He finally got in front of the owner. And that conversation was heading in the same direction. The owner offered surface-level answers, a few pain points, and the conversation was winding down towards working on a proposal he knew wasn’t going to go anywhere.

In his words: "I was about to walk away disappointed, feeling like I hadn't uncovered much real pain. But instead, I decided to dig further."

He said to the owner:

"From my selfish perspective of wanting to sell you services, I can absolutely bring you a proposal. But I don't think you're going to buy. I'm not seeing a big enough problem for us to solve."

That one statement cracked the whole deal wide open.

With some hesitation, the owner shared that the CIO's days might be limited. That he's spending $340,000 a year across three internal IT people and lacks confidence in what he’s getting in return. And that his CIO had been slow to engage throughout this entire discovery process—even though the owner himself had been pushing this initiative.

In about 90 seconds, the seller elevated himself from “IT guy sending me a quote” to a confidant and advisor. The problem being solved escalated from “maybe needing some IT help” to solving a fundamental business problem costing hundreds of thousands of dollars. And the probability of the deal increased by 10x.

It also explained why the CIO had been giving him so little to work with.

The seller’s takeaway in the email? In his own words:

"Don't walk away when you think there's only a little pain. Make the conversation uncomfortable. Keep digging. If there's gold there, you want to find it."

Couldn't have said it better myself.

When sellers come to me with problems, it's almost always about what’s happening at the end of the deal. The prospect brought in decision-makers they didn't know about. There's a pricing objection. Or the deal has stalled out and there's no urgency from the prospect.

Every time, we trace it back to the same place: discovery.

Not that they skipped it. They did it. They just didn't go deep enough.

I listen to a lot of calls, and here's the pattern I see over and over: sellers ask the scripted questions, get the standard answers, and move on. Check. Check. Check. Like they're filling out a form instead of having a conversation.

They accept surface-level answers with little to no curiosity or candor.

But surface-level pain leads to surface-level proposals. And surface-level proposals are easy to ignore, delay, or shop around.

After running, listening to, and coaching thousands of discovery calls, here’s one thing I’ve learned: There's the stated pain, and then there's the real pain. But you’ll never get to the real pain if the prospect doesn’t trust you.

And the fastest way to build that trust isn’t with slick techniques or cleverly worded scripts.

Ironically enough, the best way to build trust is through candor. It’s saying what you’re actually seeing and thinking, even when it’s uncomfortable.

That's what made this work. He didn't try to beat around the bush with a creative line of questioning. He was just honest: I don't think there's enough here for you to buy. And that honesty created more trust in a single sentence than most sellers build across multiple meetings.

He'd spent the entire process getting surface-level answers from the CIO, and even the owner up to that point. But instead of accepting it and throwing a losing proposal as a Hail Mary, he told the owner the truth. He called out exactly what he was seeing. And because he did, the real problem came out—the one that explained (and changed) everything.

Without that candor, he sends a proposal addressing some minor IT frustrations. The owner says, "Thanks, we'll review it," and that deal dies quietly in the pipeline without ever hearing the real objection. (Sound familiar? I wrote about that exact problem a while back.)

With it, he's now positioned to solve a $340K business problem that the owner is motivated to fix.

Same company. Same opportunity. Completely different deal.

If you're wrapping up discovery and not feeling like you've hit real pain—don't just move forward anyway.

Pause. Be honest about what you're seeing. You can frame it the way he did: "I can bring you a proposal, but based on what I'm hearing, I don't think you're going to be ready to move forward. I'm not seeing a problem big enough to justify the investment."

That kind of honesty does two things. First, it differentiates you from every other seller who's happy to just send a quote and hope for the best. Second, it gives the prospect permission to share what they're actually dealing with—the stuff they weren't going to volunteer.

And if there's nothing deeper? Then you've saved yourself weeks of chasing a deal that was never going to close.

Either way, you win.

Adios,

Ray