Hey there,

The most expensive problems in your pipeline are the ones your prospects have completely stopped noticing.

I see it all the time. A seller gets on a discovery call, asks "what are your biggest challenges?" and the buyer gives them the same rehearsed answer they give every vendor. The seller nods, writes it down, and builds their whole pitch around a surface-level problem that doesn't have enough weight to drive a decision.

Last week, we covered Situation Questions and how to research before you call (catch up here). Today we're tackling the P - Problem Questions - and how to dig past the rehearsed answers.

Let's get into it.

In order to build a deal that actually closes, you need problems with enough weight to justify action. That means going beyond the obvious. Research shows top-performing sellers spend significantly more time exploring problems than average performers - because when buyers clearly articulate their own pain, they're far more likely to invest in solving it.

Here's how to get there.

Instead of asking "Do you have challenges with X?", which invites a yes/no answer, ask your buyer to compare where they are to where they want to be.

"How does your current process compare to your ideal?" or "What's the difference between how your best performers handle this versus everyone else?"

This forces your buyer to articulate a gap. They're not just saying "yeah, it's a challenge,” they're describing the distance between reality and the standard they actually care about. That gap is your opportunity.

Vague questions get vague answers. And vague answers don't build business cases.

Instead of "Is your process inefficient?"

Try "How many hours per week does your team spend on that step manually?"

Instead of "Do you have trouble scaling?"

Try "What specific part of the workflow breaks down first when volume spikes?"

Specific questions produce numbers, and numbers are what your buyer needs when they're justifying a decision to their leadership. Every time you can get a buyer to quantify their own pain - hours lost, dollars wasted, deals missed- you're building the business case in real time.

Some problems don't surface because the buyer is embarrassed to admit them. Inconsistency across the team, outdated processes, manual workarounds they know they should have fixed years ago - these feel like operational failures, and nobody wants to volunteer those to a vendor.

Make it safe by normalizing it first. "A lot of teams I work with tell me they struggle with consistency as they scale - is that something you've run into?" or "Most organizations I talk to find that about 60% of their team's time goes to administrative work rather than high-value activities. How does that compare for you?"

You're permitting them to acknowledge the problem without feeling like they're confessing a weakness.

Here’s a quick lightboard explaining this topic: (click the image to watch)

That's it.

Here's what you learned today:

Your buyer already has the problems you can solve. They just need the right questions to see them clearly.

Your action step this week: Identify the top 3 pain points your solution addresses. For each one, write a contrast question, a specificity question, and a normalizing question. Bring all three to your next discovery call and notice which technique unlocks the most detail.

Next week in Part 4: We'll cover Implication Questions: how to take the problems you've uncovered and expand their weight until your buyer can't afford to ignore them.