How Letting Go Closed My Biggest Deals

Earlier this morning I was ripping down a mountain trail.
Knees locked. Jaw clenched. Hands strangling the bars like I could control the chaos. Every bump slammed through me. Every rock threw me sideways. The tighter I held, the more the trail beat me up.

Then my buddy breezes past, laughing: “Why you holding on so tight, man? Relax.”

So I did, not completely, just enough. Instantly everything shifted. The bike stopped fighting me. The trail opened up. I was present, smooth, using half the energy. For a few blissful minutes I flew.

Of course, ten minutes later I got cocky and ate shit, over the bars, dirt in my teeth, ego in the ditch. Lesson learned again: balance isn’t a one-time discovery. It’s a practice, every ride, every deal, every relationship.

Here’s what that looks like on the sales floor.

Grip too tight and you will choke the deal

When you micromanage a conversation, squeeze pricing until it caves, or over-explain features to prove your worth, you’re doing the equivalent of clenching the bars. Prospects feel the pressure. They close off. Negotiation becomes a tug of war and you end up discounting value instead of leading it.

Let go too much and you lose control.

But “relax” isn’t an invitation to be sloppy. Letting go completely, ignoring process, failing to guide the buyer, or not owning the outcome means chaos. Deals stall. Teams misalign. Growth flatlines.

The middle line is where scaling happens.

The sweet spot is a steady, confident hold: you lead the conversation, you trust your process, you let the buyer arrive at the conclusion themselves. That’s where magic happens:

• You use less energy but get better results.
• Your team doesn’t need babysitting, they need a framework and permission to run.
• You stop trading margin for motion and start trading clarity for commitment.

Tactical takeaways you can use today:

1. Loosen the grip on features. Paint the future instead, let them feel the result, not the spec sheet.
   

2. Create guardrails, not chains. Teach your team the playbook (PITCH). Let them execute without micromanage checks.
   

3. Ask for the buy-in, then be quiet. Give space for the prospect to own the decision, the most durable closes are the ones people make themselves.
   

4. Practice balance daily. Debrief your toughest calls: where did you pull? Where did you push? Tune it next time.

I’ve learned this the hard way, on trails and in boardrooms. Letting go enough to trust the ride, and firm enough to keep the line, is what turned inconsistent closers into teams that scale.

If you want a simple framework for that balance (so your reps don’t have to learn it the painful way), I pull this into every coaching call and training I run. It’s the same principle behind PITCH ME: lead, don’t squeeze.

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Ride steady, close better, scale smarter.
Kayvon

P.S. If you had to choose one place you’re gripping too tight right now (price, micromanagement, product talk), hit reply and tell me. I’ll give a quick note on how to loosen up and win it.