Why getting good at sales is the most reliable way to break what's working

One of the bigger decisions I've made this year is getting more honest about where my time actually belongs.

That's a core part of what being an Essentialist CEO means to me — not just having a business that runs well, but being ruthless about what deserves my personal attention and what doesn't.

Sales is something I'm genuinely pretty good at. I enjoy those calls — the diagnosis, the conversation, the moment when someone gets clear on something they couldn't see before. But they are also incredibly draining. And they are time-consuming in a way that was pulling me away from the work that only I can do.

So I made a decision. I needed to find someone to own that part of the business for me. Someone I could trust with it completely.

I found Samy.

Samy came on earlier this year to handle sales for the Collective. From his very first calls, he was closing at around 45%.

Not because he was a natural (although in many ways he is). He was nervous — genuinely anxious about it. But because he was nervous, he did exactly what I told him to do. He followed the framework.

Every call. Every time. And it worked immediately.

Then his numbers started to drop. Within a matter of weeks he was closing somewhere between 15 and 20 percent, and it stayed there. Nothing had changed on the surface. Same offer. Same market. Same person on the calls.

I got on a call with him to figure out what was happening.

"Are you still using the framework?" I asked.

He laughed. "I stopped for a while."

"Why?"

Another laugh. "Honestly? Because it was going so well. I figured I didn't need it anymore."

There it is.

The framework wasn't the thing holding him back. It was the thing making him good. And the moment he felt confident enough to stop using it — the moment things were going well enough that the structure started to feel like something he'd outgrown — everything fell apart.

He went back to it. The very next webinar, he closed more than he had in the entire previous month combined.

Same person. Same offer. Same market. One change: he stopped winging it.

Note: I’m not criticizing Samy for this. He’s giving me a helpful example, but we ALL do this. I’ve done it more times than I can count (and I bet you have too). We use a framework, a tool, a system to get good at something. Then we get a little cocky, think we no longer need that help, stop using it, and everything goes to shit.

Let me be clear. You are probably very good at winging it.

I mean that sincerely. The people I work with are smart, experienced, and deeply skilled at what they do. They've built careers on being capable enough to pull things off without a rigid system. They get above-average results by operating on intuition and expertise alone. That is not nothing. That's actually impressive.

I had a business partner for several years who was exactly this kind of person. Phenomenally smart. An incredible writer. Genuinely, naturally excellent at winging it — in a way that I had to respect even when it frustrated me.

When I started pushing for us to plan our newsletters further in advance, to build out a real content calendar and stick to it, she'd look at me like I was slightly unhinged. And honestly? She had a point. We were doing well. Our ability to wing it had taken us FAR. The argument for adding more structure when things are already working is not an easy one to make.

But I knew something she didn't fully buy. The thing that would take us to the next level wasn't more of what we were already doing.

Winging it gets you to good. It does not get you to great — and it does not get you to consistent, let alone predictable.

The ceiling of winging it is real. And hitting it at the exact moment you feel most confident is, in my oh-so-humble experience, exactly how it tends to happen.

Here's the part that gets me though — and I want to be honest about where my patience runs out.

I understand winging it when you're already skilled at something. You've developed real intuition through years of repetition, and that intuition carries you. Even if you can't always explain what you did, you know it works. I get it.

What I cannot wrap my head around is winging it at something you know you're not good at.

Almost every week I talk to a consultant who tells me they hate sales. That it feels hard and uncomfortable and like something they just aren't built for.

And when I ask them about their process, they look at me a little blankly. They don't have one. They show up to every call and figure it out in real time. Every conversation is different. They've never actually tried doing the same thing twice.

And then they wonder why they can't get better.

You would never approach any other skill this way. You didn't build your expertise by doing something completely different every time and hoping it stuck. You put in reps. You refined. You got feedback. You iterated on something consistent enough to actually learn from it. That's how skill works — in every domain except, apparently, sales.

(I went deep on why smart people abandon everything they know about skill-building the moment sales comes up — and what it actually costs them — in this newsletter. Worth reading if that one hit home.)

Most people think a sales framework is about sounding polished. Smooth transitions. Not stumbling over your words.

That's not it.

The framework does one thing that matters above everything else. It frees up your attention. And when you don't have it, a few things happen that are worth naming honestly.

And then you walk away from the call feeling drained and vaguely terrible about it — and you tell yourself it's because you're just not a sales person.

But that's not why you hate it. You hate it because you're trying to navigate a conversation (probably an important one) with no map and no compass.

Here's something I say to almost every client I work with: a huge part of the stress of sales calls disappears when you have a clear offer.

If you don't know exactly what you're selling — if you're trying to figure that out in real time while simultaneously trying to connect with a prospect and diagnose their situation — of course it feels impossible. You're solving three problems at once and the call hasn't even started.

But even when the offer is clear, there's a next level. You need a flow and a framework for the conversation itself. That's when it really starts to work. That's when the calls go from something you dread to something you can actually learn from, refine, and get better at over time.

Offer clarity + call structure — that's the combination that makes premium sales start to feel less like performing and more like helping.

When you have both, you can actually be present. You can listen. You can hear what someone isn't saying as much as what they are. You can notice when something lands, when it doesn't, when they go quiet in a way that means something.

That's not possible when you're managing yourself. And that inward focus is exactly what produces the most expensive failure mode in sales.

It has a name. Most people just call it being helpful, which is why it's so hard to catch in yourself.

Premature solutioning is what happens when you jump to prescribing before you've actually finished diagnosing. You hear a few symptoms, you recognize the pattern, and your brain — being the efficient, experienced thing it is — immediately knows the answer. So you start sharing it. You outline what you'd do. You explain your approach. You demonstrate your expertise.

And the call goes sideways.

There are three distinct reasons why, and they're worth understanding separately.

What you heard in the first ten minutes is almost never the full picture. Symptoms aren't the problem — and the problem you see immediately is rarely the root cause. Pattern-matching to your existing answer rather than staying curious about this specific person's specific situation means you might confidently prescribe the right-sounding thing for the wrong problem entirely. Confident and wrong is worse than asking one more question.

You already know what their problem is. You've seen it a hundred times. That's your expertise. But they haven't caught up to you yet.

They came into the call thinking "yeah, I have this problem — maybe this person can help me." Your job is to take them somewhere completely different: to "oh my God, this is so much bigger than I realized, and staying here is costing me more than I can afford to keep paying." That is a journey. It requires going deeper, asking more questions, sitting with the uncomfortable silence after a hard question lands.

If you jump ahead — if your expertise lets you skip that part — they won't feel the urgency to act. They'll say "this was really helpful, let me think about it." And you'll never hear from them again. Not because they weren't a fit. Because they weren't ready. And they weren't ready because you did the discovery work for them instead of with them.

(I covered the pre-call framework that starts this journey before you ever pick up the phone in The Pain Primer — if you're not using something like this, it's worth your time.)

Even when a prospect thinks you sound smart, something feels off. It feels like you're fitting them into a box before you know if it's the right box. The rushed prescription might earn an impressed nod, but it rarely results in a signed contract.

Here's what the prospect is actually experiencing, even if they can't articulate it.

They feel like they're being sold to instead of helped. Like you're building a case for yourself rather than trying to understand if you can actually help them.

For the attuned buyer — and your ideal clients tend to be attuned — this reads clearly. Premature solutioning signals that you need to sound like you have the answer more than you want to actually find it.

That's overcompensation. It looks like insecurity wearing the costume of expertise, which makes most of us cringe.

And even when a prospect doesn't read it that precisely, they feel something that makes them hesitate. That feeling does not close premium engagements.

More questions. Fewer answers offered before they're ready to receive them.

The shift sounds simple and is genuinely difficult, because sitting with a good question — actually waiting for the full answer instead of jumping in with the next smart thing — is one of the most uncomfortable things to do when you're used to demonstrating your expertise at every opportunity.

But when you do it well, something changes.

And then something happens that doesn't happen any other way. They get fully, viscerally clear on how bad the situation actually is. Not the polite version they came in with. The real one. "Oh my God, I didn't even realize how bad this has gotten."

That's the moment!

And when you've taken them there — when they're sitting in the full weight of it — you can ask something that completely reframes the rest of the conversation: "Are you open to hearing how I think I can help?"

Notice what that isn't. It isn't a pitch.

It isn't a transition into a presentation you've been waiting to deliver. It's an offer to help someone who has just realized, out loud, how much they need it.

And they don't feel sold to. They feel like they’re buying something they want and need. They feel relieved. They welcome it.

It lands like something they've been waiting for without knowing they were waiting. You're not closing them — you're rescuing them. And the difference between those two experiences is the difference between a prospect who needs to "think about it" and one who says yes before you've finished the sentence.

(The posture and qualifying signals that make this possible — including how to recognize when to stop pursuing entirely — are in this newsletter.)

He didn't get better between the bad month and the good webinar. He didn't develop new skills, deepen his knowledge, or figure out something he didn't know before.

He went back to the framework. That was the entire change.

The framework didn't constrain him. It gave him back the mental space to actually show up for the person on the other end of the call. To listen instead of perform. To diagnose instead of pitch. To be present enough to actually help.

And here's the part worth sitting with: he didn't stop using the framework because it wasn't working. He stopped because it was. Success confidence is one of the most reliable ways to break the thing that was making you successful. The structure isn't something you graduate from. It's something you return to — and the returning is what keeps compounding.

In love, growth, and better questions,
Kasey

P.S. The three newsletters that sit alongside this one: why the "I'm just not a sales person" story is costing you more than you think — the Pain Primer, the pre-call framework that does the diagnostic work before you ever pick up the phone — and the evaluating posture that makes qualified prospects close themselves.