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.

Here’s the thing: when emotions drive your actions, they cloud your judgment. You lose the clarity needed to make sound decisions and present yourself professionally. That’s exactly what happened to me in that negotiation. I wanted the conversation to go a certain way, but my emotional attachment to the outcome blocked me from doing what I was actually there to do—serve my client. I’ve since learned that negotiation isn’t about forcing your preferred outcome. It’s about helping your client make the best decision for them.

Another lesson that hit me hard from that experience is the importance of setting expectations. When expectations are clear, surprises are few, and surprises are what cause anxiety—for both you and your client. In any negotiation, surprises can erode trust and throw the process off course. But when you take the time to prepare your client for what might happen, you build trust. It’s almost like you’re predicting the future. The better you are at setting expectations, the smoother the process will be, and your client will feel more confident every step of the way.

I’ve also learned that your role in a negotiation is to advise, not decide. You’re not the one making the final call; your job is to present options, walk your client through potential outcomes, and let them decide what’s best. When you stay grounded in the advisor role, you maintain integrity and professionalism. You give your client the space to feel empowered by their own decisions. You are the guide—not the hero of the story.

And then there’s the matter of tone. Negotiation isn’t about winning battles—it’s about building bridges. No one wants to feel like they’re being opposed or shut down. The moment a conversation feels like a fight, rapport is lost, and it becomes nearly impossible to move forward productively. But when you approach negotiations with a collaborative mindset, the dynamic changes. The people you’re negotiating with feel heard, respected, and open to finding solutions with you. That openness makes all the difference. When people feel heard, they’re more likely to listen.

At the end of the day, negotiation is about balance. Detach yourself from the outcome so you can stay level-headed and professional. Set clear expectations so your client knows what to expect, minimizing surprises. And most importantly, remember your role as an advisor—your job is to guide, not to control. When you approach negotiation this way, you not only represent yourself and your client well, but you also create an atmosphere where productive conversations can thrive.

The next time you walk into a negotiation, ask yourself: Are you prepared to stay calm and professional, no matter how the conversation unfolds? Are you ready to set expectations, build trust, and focus on collaboration? If so, you’re already well on your way to mastering the art of negotiation.

Stay the course.

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