If you learn some of these hard lessons in communication, you’ll build a reputation as a strong negotiator.
If you want to improve your negotiation skills, start with your communication skills. Negotiation is all about communication: what to say, how to say it, and when to say it. If you should say anything at all. Sometimes, you need to shut up and listen. I call it the “pregnant pause,” and with a furrowed eyebrow and a knowing head nod, that pause can elicit so much talking from the other side.
One of the many important lessons my Nonno taught me about business was, “Never call anyone’s baby ugly.” He meant, of course, never tell anyone their idea is stupid. Also, never literally tell your friends, family, colleagues, or strangers that their child is less than the most beautiful baby you have ever seen.
I learned my Nonno’s lesson the hard way when we were negotiating a big deal with what would later become the largest CRM and platform company in the world. My company was co-pioneering a system the world would eventually know as, “The Cloud.” Negotiations were going well until our chairman just couldn’t help himself, and he called out the chairman of the other company and said, “That’s a ludicrous concept.” By embarrassing him in front of everyone, it not only drove a wedge, but it also shut down the deal.
As a talent agent, media attorney, and professor at USC Gould School of Law, I teach my students and clients how to communicate well in their negotiations. My new book, TILT the Room, which comes out in 2026, explains how you can use timing, influence, leverage, and trust to better negotiate.
Here are a few hard negotiation lessons I learned along the way.
1. Be honest.
You may have the urge to avoid the truth in a negotiation. Maybe it’s not in the best interest of your client or to put everything on the table right away. However, that doesn’t mean you should break their trust.
You might want to strategically withhold, which is different than lying with the intent that it’s going to come out later. If you do lie, however, and the other party finds out, it’ll either ruin that deal or your reputation as a negotiator.
2. Deliver bad news early.
Speaking of when you should deliver news. Deliver the bad stuff early. Some negotiators avoid mentioning the unpleasant news, hoping to hook someone before telling the downside.
However, when communicating with someone about a deal, it’s best to get the bad stuff out in the open early. I was taught this by Rob Chesnut, a respected attorney and mentor. Rob was on the founding team of Airbnb and Chegg. Rob explains that being transparent not only builds trust, it can also help cement relationships.
3. When you mess up, own it—and fix it.
Sometimes in a negotiation, you make a mistake, or someone on your team does. No one likes to make a mistake. However, don’t blame others for your (or your team’s) error. Own it and apologize. Call yourself out.
I worked with a high-ranking exec from one of the largest shoe companies in the world. He mentored many other dealmakers and told us it was always important to own your mistakes. It builds trust and encourages the other side to own their mistakes.
4) Don’t gossip or speak ill of others.
Negotiation is about respect. Respect for the process and the other side. One way to show respect is how you communicate about yourself and others. This is something I learned from my gangster friends when growing up in the streets. Their rules of communication went like this: keep your mouth shut, don’t talk crap, don’t talk to the cops, don’t snitch, and don’t gossip.
If other negotiators hear you speak ill of people who aren’t in the room, they might wonder if you’re doing the same thing about them. In fact, I teach my students and clients to do the opposite and compliment people (genuinely, of course) who are in and out of the room.
Negotiation is all about how you communicate. If you learn some of these hard lessons in communication, you’ll build a good reputation as a negotiator and have more success.