Stop trying to make prospects like me

Observation

Most of my sales calls aren’t sales calls. They’re approval auditions.

I noticed it in the small things first. I agree too fast. I over-explain decisions nobody asked about. I discount before anyone pushes back. I keep talking after the client is already sold, because silence feels like rejection. Somewhere in almost every conversation there’s a moment where I trade a real opinion for a safer one — and I can feel the trade happening, and I make it anyway.

Here’s the uncomfortable part: the prospects usually can’t tell. The calls go fine. Polite. Forgettable. And then I walk away with a gut sense that I performed a version of a person instead of being one.

Fear and resistance

What actually scares me isn’t the phone. It’s being misjudged with no chance to correct the record — the prospect deciding I’m clueless or pushy, and me just having to sit there and be that in their head.

So I manage. I pre-apologize. I soften recommendations into suggestions. I make myself smooth so there’s nothing to grab onto.

Hypothesis

The likability work isn’t just exhausting — it’s costing me deals. Prospects can smell a performance even when they can’t name it, and a person busy managing an image isn’t listening to the problem. If I drop the performance, I expect:

• shorter calls
• more “no”s
• a few dramatically better conversations
• a strong urge to go back to performing

The experiment

For the next stretch of sales calls, I’m dropping the likability project. Concretely:

1. Say the honest read, including “I don’t think you need this” when it’s true.
2. Let silence be silence. No filling, no over-explaining.
3. No discounting unless the price is actually wrong.
4. Notice the moment I want to trade an opinion for approval, and name it to myself in real time — even if I still make the trade.
5. Write down what happened internally after each call: body, thoughts, the flavor of the discomfort.

My prediction

I predict the calls will feel worse and go better. I predict at least one moment where I want to abort the experiment mid-sentence. I predict the “no”s will sting about as much as I imagine, which is the whole point of checking.

What happened so far

I’m publishing this while it’s live — on purpose. This section is a log, not a conclusion.

Sep 29 — first calls. Made three calls with the rules above. Two were unremarkable, which is itself interesting: unremarkable used to require effort. On the third, the prospect asked for something I’d usually fake enthusiasm about, and I said “honestly, I’d do it differently, here’s why.” He paused and then said “okay, what would it cost?” That has never once happened in a call where I was performing.

Sep 29 — internally. The urge to fill silence is louder than I expected. It sits in my chest, not my head. Noted, not fixed.

Oct 2 — first week. The pattern I actually see isn’t “fear of rejection.” It’s reflexes — small trained moves (apologize, soften, agree) that fire before any fear shows up. The experiment is less about courage and more about noticing a habit fast enough to choose. No lesson yet. More calls this week.

What I’m watching for

Whether the discomfort decreases or just changes shape. Whether honesty reads as confidence or as abruptness on the days I’m tired. Whether I can tell the difference between “being straightforward” and “being harsh” while it’s happening.

Follow along on the experiments page — updates land here as they happen.