Why Your Sales Pitch Falls Flat (And What to Do Instead)

I was recently asked, “What’s the most common mistake sales reps make?”

Here’s my brief answer:

They try to have a sales conversation before they’ve earned the right to have one.

Most reps are in a hurry. They’ve got targets to hit and calls to make. So the moment a prospect picks up the phone or replies to an email, they pounce. They rush straight into their pitch, rattling off features and benefits, hoping something lands.

But here’s the problem: your prospect isn’t ready for that.

Unlike you, they don’t think about your product all day, every day. Before they take (or return) your call, they need to believe you’re someone worth talking to and that you have something worth talking about.

You can’t skip those steps and expect a good outcome.

Real sales conversations don’t happen in a vacuum. They’re the result of a progression.

Conversations about problems lead to discussions about solutions, and those lead to conversations about working together.

Most reps? They jump straight to the third one. They’re pitching a solution before they’ve uncovered a problem. They’re thinking about (and often offering!) answers before asking meaningful questions. And it shows.

Your prospects know when they’re being pitched, and they shut down the moment they feel like a target instead of a person.

That’s why the best reps don’t pitch; they guide the conversation. Here’s how they do it:

• They have a hypothesis in mind about a priority that’s tough to execute on.

• They validate whether the prospect is even thinking about that same priority right now.

• They ask if it’s worth digging into, while offering insight or expertise.

• They promise to trade value for time in that first meeting, regardless of the outcome.

• They use that first meeting to establish fit and build credibility before moving forward.

They seek first to understand, then to offer insight. Only when they’ve uncovered something meaningful—something worth solving—do they begin connecting the dots between that problem and the solution they represent.

This isn’t happening nearly as often as it should be (gesturing wildly while looking around…).

That progression, problem → solution → sale, isn’t just a framework. It’s how trust is built. It’s how relevance is established. It’s how value becomes obvious.

When you skip to the end, you rob the prospect of the opportunity to trust you. You force them to do the work of connecting the dots. You make them figure out why they should care.

That’s just too much to ask a prospect to do, especially without them even knowing who you are or believing you’re someone they should listen to.

This is part of a series I’m doing on sales mentorship, the questions I often get asked by new reps, and the mindset shifts that helped guide my career path in a positive direction.

I’m doing a live interview series for charity this summer, and I’ll be covering the same topics with some friends who have mentored and inspired me. You can join us and participate by making a donation to Chosen Vision. Learn more here.

So the next time you’re tempted to jump ahead, remember that you have to earn the right to have the conversation you want to have.

Slow down. Get curious. Build trust.

Cheers,
JB