I read a great piece recently by Julie Thomas, “Creating Urgency Without Pressuring Buyers,” and it hit on something I see all the time with sales teams—especially when deals stall late.

Her core point is right: urgency doesn’t come from the seller. It comes from what’s genuinely at stake for the buyer.

In my work as a sales coach, I see things break down much earlier in the process.

Most sellers don’t stay in the pain long enough. They hear the first inkling of an issue and immediately try to fix it.

The Tip of the Iceberg

They stop at the “tip of the iceberg”—the visible, surface-level issues the buyer is willing to share early. A little frustration. A few inefficiencies. Something that “could be better.”

But a little pain isn’t a reason to change.

Great reps “wallow in the pain”—not in a negative way, but in a disciplined, curious way where you resist the urge to move too quickly to solutions. Instead of uncovering one or two issues and jumping to how you can help, these great reps ask questions that help them really understand what’s sitting below the waterline.

This is what I’ve talked about before as “filling the bucket.”

It’s not about finding a problem—it’s about uncovering the system of problems, how they connect, and what they are actually costing the business and the people inside it. The best sellers I work with stay in that space longer than feels comfortable. They keep asking, keep connecting dots, and keep building the case for change before ever trying to solve anything.

Because what’s under the surface—the operational drag, the financial impact, the risk to customers, the personal pressure on the buyer—that’s where a real reason to change lives.

People don’t change unless there is a reason to. “This looks better,” or “we’d like to try this,” won’t make them change, at least not with any kind of timeline attached to it.

A Second Mistake

When reps struggle with uncovering enough pain to build a business case for change, they often make a second mistake, too.

When deals slow down, the instinct is to push harder—add a discount, create a deadline, or ask what it would take to close this quarter. It feels proactive, but it usually has the opposite effect. Buyers recognize manufactured urgency immediately and, instead of moving forward, step back.

What you end up with are longer sales cycles, lower conversion rates, and a pipeline full of deals that require constant “staying in touch” with no real movement.

Even worse, it chips away at credibility. When you try to close without a compelling reason for the buyer to act, you don’t come across as a trusted advisor—you come across as a sales rep who needs to sell something.

Real urgency feels very different.

It shows up when the buyer starts to articulate, in their own words, what it’s costing them to stay where they are—operationally, financially, and personally. That doesn’t come from a well-timed closing question. It comes from doing the work up front to fully understand the problem, its impact, and what happens if nothing changes.

And even then, there’s one more layer that often gets missed.

What’s a “Strong Business Case”?

A strong business case creates interest. Quantified impact creates momentum. But commitment usually comes down to something personal—how the situation affects their success, their team, or their ability to deliver on what they’ve promised to their customers, donors, or students.

If you don’t get there, deals stall, even when everything else makes sense on paper.

The takeaway for me is simple.

Stop trying to create urgency at the end of the process, and spend more time earning it at the beginning. The more time you spend below the surface, the more likely you are to uncover what will actually compel a buyer to act.

And if you’re hearing a lot of “we’ll try this when the time is right,” it’s usually not a closing problem.

It’s a signal that you didn’t dig deeper, didn’t connect problems to impact, and never got past the tip of the iceberg.