Letting Go of the Playbook
Sales is supposed to be about persuasion. I’ve found it’s more about presence.
The Playbook Trap
When I first started in software sales, I thought success meant control.
Control of the conversation. Control of the questions. Control of the outcome.
I read the guides, memorised the frameworks, and armed myself with every technique I could find. Meetings sometimes felt more like FBI interrogations than conversations.
It worked - at least, it worked enough. But it never felt quite natural. And I’m sure my customers could probably sense it too.
What Happens When You Let Go
Over the last couple of years, something shifted. As I got more comfortable in my role and more confident in what I actually knew, I started letting go of the script.
I stopped treating meetings like performances and allowed myself to just be there. Not every silence had to be filled. Not every question had to be perfectly sequenced. And I didn’t have to take notes on everything under the sun.
And that’s when things became easier. Conversations flowed more naturally, prospects seemed more open, and trust built itself without me forcing it.
The Desperation Problem
Of course, this is much easier to do when you’re ahead. When you’re tracking well for quota, leaning back feels safe.
But when you’re behind, it’s harder. Every deal suddenly feels like it has to close, and that’s when the nerves creep in. I catch myself overthinking, tightening up, and trying to steer things too much. And prospects can usually pick up on that energy, whether I want them to or not.
It’s strange, isn’t it? The more you need the deal, the harder it seems to get.
Beyond Sales
What struck me is how much this applies outside of work too.
In friendships, relationships, even creativity - when I try to over-control things, they get rigid. But when I loosen my grip a little, the space seems to open up for something better to happen.
Letting go doesn’t mean not caring. It’s more like trusting that I’ve done enough to show up as myself, and that’s usually the best place to start.
The Quiet Confidence
Some of the best people I’ve learned from, in sales and in life, carry this quiet confidence. They don’t need to force anything, they don’t need to push too hard. They just show up, grounded in who they are.
That’s what I’m learning to practice. And funnily enough, it’s worked better than any playbook I’ve tried.
Maybe the best way to sell isn’t to sell at all. Or at least, not in the way I once thought.