The #1 Sales Question You Aren't Asking

Why prioritizing pain is the key to winning more deals

There’s one question you can ask on a first sales call that will dramatically increase the odds you win the deal.

And almost every salesperson I work with forgets to ask it.

Want to know what it is?

Here you go:

“Which of those challenges is costing you the most time, money, or sanity? Like, of all those problems you mentioned, which is your #1 problem?”

I want you to notice something about that question: It can’t be the first question you ask someone. Why? Well, to state the obvious, it’s a follow-up question. It presupposes that you’ve already gotten the prospect to spill their guts a bit about what’s going on with them and their work. More specifically:

1. It presupposes that you’ve gotten them to share what’s challenging about their work (i.e., naming the obstacles/problems standing between them and the results they’re paid to create).

2. It presupposes that you’ve uncovered the personal impact of those challenges (i.e., what’s painful for them about all the stuff they shared in #1).

Most salespeople are actually decent at doing #1 and #2. Every sales methodology ever created has beaten this stuff into us. We know we’re supposed to ask questions about what people are dealing with. We know those questions are supposed to help us find pain.

But the step that most salespeople skip is prioritizing that pain. And that’s a mistake.

A mistake that’s keeping you and your team from winning deals you deserve to win.

Why Prioritizing Pain is So Important

You see, finding something painful about someone’s job is not that hard. Literally every human being does their work in under-optimized conditions. All of us have a vision of what an ideal state of work would look like if our job were frictionless. There’s a big gap between the reality of our work and that ideal, perfect-world state. That gap is where the pain we look for as salespeople lives. Most of us are pretty good at creating a conversation about that gap. We have to get talk about that gap if we want to make our sales pitch relevant to the person in front of us. Otherwise we’re just brochures with legs.

However, as my friend Rob Snyder likes to say:

“Life is a series of pain points we mostly do nothing about.”

This is true for all of us. We’re all working around a million little sources of friction that we’ve decided we can live with. We feel a little pain, but we just keep soldiering on. Despite the fact that almost everyone out there has a long list of things they’d change about their job if they could, there are very few of those changes we’re willing to commit to doing something about.

Let me say that again more succinctly.

All of us have pain. But not all of that pain is worth doing something about. Not even close.

And that tension is absolutely critical for salespeople to accept, understand, and use.

You see, sales happen when pain rises to the level that someone is willing to do the work to secure resources to alleviate said pain. Resources in the form of money, yes. But also resources in the form of attention from their boss, political capital to champion a vendor selection process, cycles spent teaching people how to use a new tool, and credibility risked on a bet that this thing will actually make things better.

But how many of the little challenges rise to the level of “I need to fix this now”? How many of those million little pain-points are big and costly and annoying enough to will you to ask for budget, convince your team, and do the work of implementing some kind of solution?

Not many. And just like you, at any given time, there might only be one or two real problems this person you’re trying to sell is genuinely committed to solving. And if you only know the list of problems, and not their relative priority, you have no idea how committed your prospect really is to securing the resources you need as a salesperson to win the deal. You’re guessing when you should be sure.

Think about it mathematically. If someone has ten problems and you solve their seventh-most-painful one, they might like you. They might even agree that your product is cool and would probably help (how many times have you heard this from a prospect who ghosts you later?). But “cool” and “would probably help” doesn’t get you a signed contract. It gets you stuck on someone’s “nice to have” list while they silently de-prioritize you in favor of the two or three other vendors who can provide proof that they can solve problems one, two, and three.

You need to know where you rank. You need to know not only what hurts, but what hurts the most.

Because if you’re not near the top of their list, you’re not going to win the deal.

What This Unlocks

A while back, one of my portfolio companies was struggling with demo conversion rates. We were getting better at discovery, but when we got to the demo, we kept losing deals.

The problem? Our demos were still generic product tours. We’d uncover five or six pain points in discovery, then show up to the demo and walk through every feature in the product from beginning to end. We covered everything, but we never clearly proved we could solve the #1 problem the prospect cared most about.

Once we started asking the “which of those is your #1 problem” question in discovery and using the answer to plan our demos, everything changed. Not just because we learned what mattered most to the prospect. But because now we had permission to build the entire demo around the #1 problem they cared about.

We stopped trying to be comprehensive and started trying to be compelling. We started spending 70% of the demo proving we could solve their #1 problem, and left room in the rest of the agenda to show them we could handle their other problems (and answer any questions that arose naturally from our new, more-relevant, more conversational demo).

And, just as you might imagine, our close rates went up.

Because we now knew what their #1 pain-point was.

And their #1 pain-point became our pitch.

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When you know what’s costing someone the most time, money, or sanity, you don’t have to guess anymore about what will resonate with them or what will drive urgency. You know what hurts the most. You know the problem they care most about solving. And you know exactly what you need to prove as a salesperson.

And knowing that is what allows you to make the natural shift to the most powerful moment in any sales conversation.

The moment when you can credibly say:

“I get it. And I think we can help.”