Find more pain on your sales calls, a real call breakdown

If you're stuck getting surface level answers on your calls, I guarantee it's not your closing. It's your discovery. You're not asking the right questions to dig past what they tell you first. Let me show you exactly what that looks like on a real call.

When I was new to sales, I fell into this trap constantly. My conversations stayed surface level and then I just hoped something I said would click in the prospect's mind and they'd hand me their money. I got some sales that way. But it was inconsistent as hell. It wasn't until I learned the right questions, and how to actually navigate a conversation to get below the surface, that my numbers got consistent and kept growing.

I've closed $9M+ in sales over the years, coached thousands of reps, and the biggest skill gap I see over and over is this. People can't get to the real pain. And it usually traces back to one thing: how they start the call.

Get direction before you dig

If you don't have direction at the start of the call, you'll never get below the surface. This is especially true on inbound leads. The prospect came to you for a reason. Your job in the first few minutes is to find out exactly what that reason is.

The question I always ask is simple:

Do you know what you're looking for specifically?

Then I follow it up with something like, "what have you actually seen so far that's even got you looking at this?" That one question almost always gets them to start talking about their real pain, instead of giving you a generic answer.

On the call I reviewed, my client skipped this. He jumped straight into "tell me what you're doing" without first finding out what specifically brought the guy to him. I told him straight up:

I need to have a little more direction as far as what his problems actually are, to keep it on point with what you guys do.

Without that direction, you're just collecting information with no target. With it, every question you ask after has a purpose.

Watch for status games early on

On this call, the prospect opened by trying to show he already knew how the business worked. He called the offer "a trick," said he'd heard about it before, and started grilling my client with questions like he was the one running the show.

That's a status move. He's putting the focus on you, the rep, and acting like he already has you figured out. If you let that sit, you lose control of the conversation before it even starts.

My advice on this was simple. Don't fight it, diffuse it.

We can definitely go over all those options for sure, we don't really have a one size fits all, it really just depends on where you're at now compared to where you want to be.

Then get the conversation right back on him. The second you let the prospect make it about proving what they know, you've lost the frame. Diffuse it fast and steer it back to his situation.

Stop assuming, start asking

This was the biggest pattern I caught on the call. My client kept making statements instead of asking questions. He'd hear something and immediately label it.

Example. The prospect said he runs out of cash and can't grow. My client jumped in with "so that sounds aggravating" and labeled it an emotional pain point. Sounds good on the surface, but here's the problem:

I don't like you labeling your words on someone else, because it could be the exact same feeling he's feeling, but he might verbalize it differently.

Instead of assuming the word, ask for it. Something like:

Not being able to grow the way you want, how does that actually feel on your end?

Let him tell you the word. Maybe it's "frustrating." Maybe it's something totally different. Whatever word he gives you, that's the word you use for the rest of the call. In the presentation. In objection handling. His words hit different than your words ever will.

A good drill if you want to fix this fast: listen back to your own calls. Every time you catch yourself making a statement, ask yourself if there was a way to turn that into a question instead.

Quantify everything, don't leave it vague

Another spot I flagged. The prospect said he wanted to "double" his properties and grow his net worth. My client moved on without quantifying it.

Vague goals don't create urgency. Specific numbers do. If someone tells you they want to double something, ask what double actually means in real numbers. What are they at now. What would double actually look like. If they say they'd cut their timeline in half, ask what that timeline currently is.

Same thing applies to cost of inaction. The prospect mentioned hard money lending at 10 to 15 percent. I told my client to quantify that right there on the call.

How much would he actually be taking out in hard money lending? Is he taking out 100,000? 200,000? What would the interest be on that? So we're talking about him paying over 20,000 in interest. That could be trouble.

That's the difference between a prospect nodding along and a prospect feeling the actual weight of their problem. Numbers make pain real. Vague words don't.

Dig two or three layers deeper than feels comfortable

Most reps stop at the first sign of pain. The prospect says something close to a problem and the rep moves on to pitch. That's leaving money on the table every single time.

On this call, once the prospect started opening up about running out of cash, there was a real opportunity to go two or three questions deeper. Ask how long this has been going on. Ask for an example of when it actually happened. Ask what it's costing him in deals he can't get to. Each question peels back another layer.

Just take a little more time, ask two to three more questions, and once he says the word that he actually feels, write it down. That's what you leverage later in the conversation.

This isn't about being pushy. It's about being thorough enough that the prospect feels truly heard and starts connecting their own dots about why they need to change something now.

The bottom line

Finding real pain isn't about some magic question. It's about direction at the start of the call, diffusing status games fast, asking instead of assuming, quantifying everything with real numbers, and digging two or three questions past where it feels comfortable to stop.

If your close rate feels inconsistent right now, go back and listen to your last five calls. Count how many times you made a statement when you could have asked a question instead. That one habit change will do more for your pain-finding than any script ever will.