Why the most systematic people I know wing it on sales calls (and then blame their personality)

Nearly every client I work with tells me the same thing in our first conversation:

"I hate sales calls. I feel pushy and uncomfortable. I'm just not a salesperson."

And I get it. I do.

But I'm going to challenge you about that story you're telling yourself. It's not the truth, not really. It's an excuse that's keeping you stuck.

Let me explain.

When someone tells me they're "bad at sales," it's almost never actually true. What's usually happening is one of two things:

If you can't articulate your offer with confidence—what it is, who it's for, what transformation it delivers—of course, you're going to feel uncertain on sales calls. You're not bad at sales. You're trying to sell something you haven't fully defined yet.

And that is haaaaaaaaard.

Convincing. Overcoming objections. Handling resistance. Closing hard.

That version of sales feels gross because it IS gross. And since you're not a gross person, you assume you're just not cut out for it.

But here's what nobody tells you:

That's not what good sales looks like. Your resistance to it isn't a weakness. It's a sign you understand something most "salespeople" don't.

I started my career in B2B sales. And frankly, I was naturally pretty good at it. I could connect with people, read the room, think on my feet.

But I flamed out. Got frustrated. Eventually left sales entirely.

Why? Because no one ever taught me how to have a solid, repeatable process.

I was winging it every single time. And when you're selling something simple, reading a script works fine.

But when you're selling something more complex, like the consulting and coaching work most of you do, winging it hits a ceiling really freaking fast.

If you missed it, I talked all about this idea and how it shaped my theme for 2024 and became a HUGE part of how I went from inconsistent $10k months to consistent $30k-$50k ones.

I didn't leave sales because I wasn't cut out for it. I left because I was exhausting myself reinventing the wheel on every single call, and I didn't know there was another way.

That's what I see with most of my clients. They're smart. They're good at what they do. Some of them are even naturally good at connecting with people.

But they've never built a process. They've never tried doing the same thing consistently enough to know what actually works.

They let the prospect lead. They react instead of guide. And then they wonder why it feels so hard.

It's not your personality. It's not some deep resistance to being "salesy."

It's that you've been treating sales like something you either have or you don't, instead of a skill you can actually learn.

Now let me tell you about the opposite scenario.

One of the best salespeople I know is Reuben Shears. He’s been a core partner in building the Essentialist CEO Collective and has become a good friend.

Reuben is an avowed introvert. He has dual degrees in astrophysics and math. He is the epitome of "not a sales guy." No natural gift-of-gab. No charisma-driven schmoozing. He's not working a room or charming anyone into anything.

And yet he consistently closes at rates that would make most "natural salespeople" jealous.

The difference? He has a solid, standard process that he uses every single time.

Clear steps. A framework he follows. Questions in a specific order. He's not winging it and hoping his personality carries him through—he's executing a system he trusts.

So here's the picture:

What does that tell you?

Talent without process hits a ceiling. Process without "natural talent" still wins.

The variable that matters isn't your personality. It's whether you've actually built something repeatable.

So when you say "I'm just not a sales person,” let me ask you something uncomfortable:

Have you ever actually tried to learn?

Not read a book once. Not sat through a webinar. Actually tried to develop a repeatable process and follow it consistently?

Here's something I've noticed about the consultants and experts I work with:

They'd NEVER dream of winging it in learning the skills that deliver exceptional results for clients.

But sales? Totally different story.

For some reason, they treat sales like they're just supposed to magically know how to do it. Like it's a personality trait you either have or you don't—not a skill you can actually develop.

So they never create an environment where they can learn. They never build a system they can practice and refine. They just show up, wing it, and then blame themselves when it doesn't work.

I don't know what it is about sales that makes smart, systematic people abandon everything they know about skill-building. But I see it constantly.

Most of the clients I work with, when I dig in, have never actually given themselves a real chance to get good at this. They show up to every call and improvise. They let the prospect lead the conversation instead of guiding it themselves. They do something completely different every time.

And then when it doesn't work, they tell themselves "I'm just not good at sales" instead of recognizing the truth: they've never approached it like the learnable skill it actually is.

Winging it is not a strategy. Even if you're naturally talented.

We all hate being sold to.

That feeling when someone's pushing something you don't want. When you can sense their agenda. When you feel like a target instead of a person.

It's awful. We've all been there. And most of us have sworn we'll never make anyone else feel that way.

But we all LOVE buying things we actually want.

Think about the last time you bought something you were genuinely excited about. Maybe it was a course, a service, or even just a product you'd been eyeing for months.

That experience—when done right—is kind of thrilling. It's empowering. You're making a choice that's going to improve your life or business. You're in the driver's seat.

The difference between "being sold to" and "buying" isn't the transaction. It's who's in control.

When someone is selling TO you, they're in control. They have an agenda. You're a target.

When you're buying, YOU'RE in control. You're gathering information. You're making a decision that's right for you.

Your job on a sales call isn't to sell.

It's to create the conditions where they can buy with clarity and confidence.

Think about what happens when you go to the doctor.

You don't walk in and diagnose yourself. You describe symptoms. "It hurts here. This started last week. It gets worse when I do this."

The doctor's job is to connect those symptoms to the actual problem, which you couldn't have articulated yourself. You know something's wrong. They know what it means.

That's your job on a sales call.

Your prospects are symptom-aware, not problem-aware. They know things aren't working. They can describe what's frustrating them.

But they can't connect the dots to the root cause. That's YOUR expertise.

If you caught Thursday's newsletter on the Pain Primer, this is exactly why that framework works. You're not asking them to describe their problem—they can't.

You're showing them their problem through your framework. They discover the scope of their own pain by selecting symptoms they recognize.

The discovery happens TO them. Not through you extracting information.

And when you do this well—when they feel like you understand their situation better than they do—they don't feel sold to. They feel seen. They feel like they're finally talking to someone who gets it.

That's not pushy. That's helpful.

Here's where I'm going to push you:

And here's what these stories do for you: they protect you from having to actually try.

As long as you believe you're "not a sales person," you don't have to sit down and learn a process. You don't have to practice. You don't have to do the uncomfortable work of getting better at something that doesn't come naturally.

You get to keep winging it, keep blaming your personality, and keep wondering why your income is unpredictable.

But the math doesn't lie. If your close rate is 25% and it could be 60%, that's not a personality problem. That's a skill gap. And skill gaps are fixable.

The question is whether you're willing to stop hiding behind the story.

Here's the principle I want you to take away:

Your job is to make sure the buyer feels like they're in the driver's seat.

→ They share the important information. → They articulate their symptoms. → They calculate the cost. → They decide whether this is a priority. → They determine if you're the right fit.

You're not dragging them anywhere. You're creating a space where they can figure out what they actually want. And then offering to help them get there if it makes sense.

When you do this well, something magical happens:

And you STOP dreading calls. Because you're not pretending to be someone you're not.

You're just being the expert you already are, helping someone figure out if you can help them.

The Pain Primer gets them ready before the call. What you do ON the call matters too—but that's a conversation for another week.

What would change if you stopped telling yourself you're "not a sales person"?

What if the only thing standing between you and sales calls you actually enjoy... is a process you trust?

That's not a personality transplant. That's a skill you can learn.

The question is whether you're willing to let go of the story that's been protecting you from trying.

With love, growth and service,
Kasey