The Biggest Mistake I Made in a Negotiation (and What I Learned)

There’s something unique about negotiations. It’s one of those rare spaces where everything is laid bare—who’s prepared, who isn’t, who can navigate the subtleties of communication and who lets emotions cloud their judgment. It’s an intense experience, where preparation can make or break the outcome. Those who come in ready, with a plan and the right frame of mind, usually walk away feeling good about the process, if not entirely satisfied with the outcome. But negotiation is rarely straightforward. It’s almost always a challenge.

One negotiation in particular stands out for me—an experience that, looking back, was humbling. I was representing a close friend who was selling his condo. At the time, I let my emotions get the best of me. I had a very specific outcome in mind, one that I thought was best for everyone involved, and I couldn’t see beyond it. My friend and client, ironically, was the one who showed up level-headed and composed—the way I should have been. I allowed my frustration to creep into the conversation, and instead of being a professional, I ended up coming off as emotional and unprepared. It was embarrassing.