Playing Your Hand

On negotiation, leverage, and learning when to reveal.

I just accepted a new job at Oats Overnight. Which means I just finished negotiating.

For the record, I’m an average negotiator. In business school, we ran simulations in our negotiations class. I almost always ended up with a good deal, never the best. But I’ve come to believe that consistently good deals compound into something better than occasional great ones. And people have told me I negotiate well. So maybe average is underselling it. Or maybe I’ve just learned to work with what I’ve got.

Here’s what I’ve got: I can’t bluff.

I tell too easily. My face, my voice, something gives it away. So I’ve never been able to sell a position I don’t actually hold. For a long time, I thought this meant I couldn’t play my cards close to my chest. That I was stuck being readable, and therefore stuck leaving value on the table.

But I’ve learned something. People can’t always read me the way I think they can. The gap between what’s happening inside and what people actually see is bigger than it feels. I assume I’m transparent. I’m not always. None of us are.

This is the art of leverage. Not lying. Not bluffing. Just understanding that you don’t have to reveal everything to be truthful. Omission is not deception. Timing is not manipulation. You can hold cards without hiding them. You just choose which hand to play them in.

Think about it like a card game. You may have collected certain cards over the course of play. But when you play them, and in what combination, determines whether you win. The cards don’t change. The sequencing does. The context does. The read you give your opponent does.

In a negotiation, you might have multiple truths. You have other options. You have constraints. You have priorities. You have flexibility in some areas and not others. All of these are real. But which ones you lead with, which ones you hold back, which ones you reveal only when asked directly: that’s the craft.

I’m not suggesting you lie. I’m suggesting you recognize that truth has structure, and structure has power.

The other thing I’ve learned is that this doesn’t come naturally. At least not to me. My instinct is to put everything on the table, to be fully transparent, to let the other side see exactly where I stand. It feels honest. It feels fair. But it’s also how you give away leverage you didn’t need to give away.

Emotional players do this. They react. They reveal. They let the pressure of the moment override the strategy they planned. I’ve done it. I’ve watched myself do it and known I was doing it and still couldn’t stop.

But knowing it’s a pattern is the first step to breaking it. You can learn to pause before you speak. To ask yourself: does this need to be said right now? Does revealing this help me or hurt me? Is this truth serving my goals, or am I just uncomfortable holding it?

It’s a skill. Like any skill, it gets better with reps. And like any skill, the people who treat it seriously outperform the people who wing it.

You have a duty to set yourself up for success. No one else is going to do it for you. The other side of the table is thinking about their leverage, their timing, their sequencing. If you’re not doing the same, you’re not being noble. You’re being unprepared.

The cards you hold matter. But so does knowing when to play them.