The Inner Game of Negotiation

“The third type of person, before deciding to overcome the obstacle, tries to find a viewpoint where what is on the other side of the obstacle can be seen. Then, only if the reward is worth the effort, does that person attempt to overcome the obstacle.”
— W. Timothy Gallwey
The Inner Game of Tennis

A few weeks ago, I mentioned Chesterton’s Fence — the idea that before removing a barrier, we should first understand why it was built.

The principle is straightforward: If something stands in your way, pause long enough to ask what purpose it serves. Only then decide whether it should be removed.

Recently I’ve been reading The Inner Game of Tennis, a book that has me thinking about negotiation in new ways. Curiously, it brought me back to Chesterton.

Over the next few posts, starting today, I want to explore a few of these connections. I hope they give you pause for thought, too.

First published in the 1970s, Gallwey’s book became a classic not because it teaches tennis technique, but because it examines the mental side of performance — the internal battles that shape how people compete, decide, and perform under pressure.

I should confess that I don’t play tennis, and pickleball has not yet claimed me. But I’ve always been interested in athletic performance more broadly. As a kid I played baseball. As an adult I’ve spent plenty of time running long races. And for years I’ve watched my kids compete on soccer fields all over creation.

Across those arenas, the same pattern appears: The real contest often begins in the mind.

Gallwey describes three common responses to obstacles. Some people walk away. Others immediately attack the problem in front of them. A third group pauses first, trying to find a vantage point from which they can see what lies on the other side of the obstacle before deciding whether overcoming it is worthwhile.

In negotiation, we often default to the second approach.

A stubborn demand appears, and the instinct is to defeat it.
A comment feels unfair, and the impulse is to respond.
A position seems unreasonable, and energy is directed toward correcting it.

Obstacle → effort → victory.

But in mediation, I’ve repeatedly watched capable professionals expend enormous energy overcoming obstacles that ultimately didn’t matter very much. Arguments are sharpened. Positions are defended. Points are scored. Yet the overall trajectory of the negotiation barely changes.

Often the obstacle isn’t the real problem.

The unexamined urge to overcome it is.

Gallwey notes that while worthwhile things often require great effort, not all great effort leads to worthwhile results. Effort misapplied is simply motion.

In tennis, experienced players understand this instinctively. Not every difficult shot is meant to be attacked. Sometimes the wiser move is simply to return the ball deep, reset the point, and wait for a better opportunity.

Negotiation works much the same way.

Not every obstacle deserves force. Some reveal information about priorities. Some signal emotion rather than substance. And some, when viewed from a different vantage point, lose much of their significance.

Before applying pressure, ask a simple question:

If I overcome this, what actually improves?

Does it move the negotiation toward resolution?
Does it clarify the real issue? Does it move us closer to a worthy goal?
Or does it merely satisfy the impulse to win the point in front of me?

That brief pause, the moment Gallwey describes, can change the quality of a negotiation.

Not every obstacle is meant to be overcome.

Next time: What happens when we focus only on winning?

If this post resonated with you . . .

The Stoic Negotiator explores the inner game of negotiation — the mindset required to think clearly in conflict and make better decisions under pressure. Drawing on decades of mediation experience and the practical wisdom of Stoic philosophy, the newsletter examines how we can approach everyday disputes with greater discipline, objectivity, and empathy.

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