Recently, Jack Tame asked me a question on stage:
“How do we assess our skills in selling? How do we know if we’re any good before the sale happens?”
It’s a great question.
Because most people measure selling by one thing.
Did they buy?
But that’s the final metric.
The real indicators show up long before money changes hands.
And I know that because I used to get it wrong.
When Selling Felt Tense
There was a time when jumping on a sales call would spike my heart rate.
My mouth would go dry.
Pricing felt uncomfortable.
There was tension in the air.
I was good at building rapport. I’ve always had that skill.
But underneath it, I felt pressure.
I felt like I had to sell.
And that internal pressure created external tension.
The people on the call could feel it.
Looking back, I realise something important.
Early in business, you often need the sale.
Financially, emotionally, psychologically.
And when you need the sale, you try to manage the call.
You steer it.
You justify pricing.
You talk more than you listen.
You anticipate objections before they even arise.
Even if you’re not forcing a square peg into a round hole, the energy feels slightly off.
Because you’re convincing.
Not understanding.
The Shift That Changed Everything
The biggest change for me was mental.
I stopped trying to sell.
And I started coaching.
That distinction matters.
I was trained in coaching. I taught coaching for years.
Yet in sales conversations, I was managing instead of coaching.
When you manage a call, people feel handled.
When you coach a call, people feel understood.
The only directive I now carry into a consult conversation is simple:
How can I help this person?
That’s it.
If they buy, great.
If they don’t, have I added value anyway? Have I helped them think more clearly about their problem?
The moment I released the pressure to close, the tension disappeared.
And everything became easier.
How You Know It’s Working
Jack’s real question was this:
How do you know in the moment?
You know by the micro-signals.
They lean forward.
They nod.
They mirror your posture.
They interrupt with, “Yes, that’s exactly it.”
They smile in recognition.
They say, “How did you know that about us?”
That’s resonance.
That tells you your empathy is landing.
And empathy is not being nice.
It’s pattern recognition built from listening to hundreds of real conversations.
It’s what I learned from years of follow-up calls where clients told me exactly what was going wrong in their organisations.
When you’ve done that work, you’re not guessing.
You’re naming what they already feel.
And when someone feels seen, trust accelerates.
Confirmation, Not Persuasion
When selling works well, it doesn’t feel like selling.
It feels like confirmation.
You reflect their problem clearly.
You articulate the pain accurately.
You share a story of someone who faced something similar and solved it.
Not as a tactic.
As empathy.
Often people are slightly embarrassed by the problems they’re facing.
They think they’re the only ones.
When you tell a relevant customer success story, you remove that isolation.
You say, without saying it directly, “You’re not alone.”
That builds safety.
And safety builds trust.
When trust is present, hard selling disappears.
People effectively say, “That’s it. That’s what we need.”
The Hidden Metric
So how do you assess your selling skill?
Ask yourself:
- Does the conversation feel tense or relaxed?
- Am I talking more than I’m listening?
- Am I managing the call or coaching it?
- Do they feel handled or understood?
- Is there pushback, or is there alignment?
Revenue is a lagging indicator.
Resonance is a leading one.
When you diagnose accurately, empathise deeply, and remove pressure, selling becomes lighter.
It becomes cleaner.
It becomes easier.
The day I stopped trying to sell and started trying to help was the day my selling improved.
Not because I got more persuasive, but because I got more precise.
