How To Use Timing To Your Advantage When Making Deals

This expert opinion by Ken Sterling, Executive Vice President at BigSpeak, was originally published on Inc.com.

People make deals every day. You don’t need to be in a boardroom or on the golf course to make deals. When you are making deals, timing is essential. When you do something is just as important as what you do. 

For example, when you walk into a room to negotiate with another party, setting the terms is all about timing. You can’t reveal your price too soon or you’ll risk getting a bad deal or perhaps no deal at all (which isn’t always a bad thing, because maybe it was a terrible deal that your company would have lost money on!) You want to reveal your ceiling or floor number only when it can be most useful, usually after you’ve learned what the other person is willing to offer. 

As a talent agent, media attorney, and professor at USC Gould School of Law, I teach my students and clients how to use timing to tilt deals in their favor. I’m also working on my new book, TILT the Room, coming out in 2026, which explains how you can use timing, influence, leverage, and trust to win people over, close deals, and get better terms. 

In the meantime, here are some key timing tips I learned from my lifetime of dealmaking in backrooms, boardrooms, and private jets. You can use these tips whether you’re negotiating a multimillion-dollar merger with a startup or negotiating for a used bicycle on Facebook Marketplace. 

Go From Easy To Difficult. 

In dealmaking, get the easy stuff out of the way first. Leave the hard stuff for the end. For example, in divorce mediations (which I’ve been part of as a client, attorney, and mediator), we always start with the community property, because it’s easy to do. Also, there is usually less emotional entanglement. Then, we move to figure out support payments and finish with the kids, usually the most charged and triggering negotiations in a divorce.  

And the reason we start with the easy stuff is that it may be easier to settle. Then, once you have a few wins racked up, it’s easier to segue into the tricky stuff. 

Use The Pregnant Pause. 

In dealmaking, learn to leverage silence. People have a tendency to fill the void with words, and it can ruin deals. 

I like to call it the “pregnant pause.” It’s not just a pause in the conversation. It’s the weight of the pause. So, after you say your piece, stop talking. Let the other person absorb what you said. Don’t go into a staring contest. Have a slight, friendly look on your face. Maybe tilt your head ever so slightly. Conversely, after the other party says something to you, don’t respond right away.  

The silence might prompt them to reconsider and offer something better. Or at a minimum, the silence is uncomfortable for them, and they keep talking and offering better deal points. 

Avoid Looking Thirsty. 

Eager people make poor dealmakers. You want to avoid looking thirsty. For example, I was representing a client in a big deal, and we sent our terms to the other party. My client was anxious. He kept pestering me to call to see if the other party had received our email about the terms. 

Don’t do this. Whenever you’re thinking of emailing someone, like, “Hey, just making sure you got my email?” or “Hey, what are you thinking?” wait another day. If you appear thirsty, you give the other person leverage. They have you, and they know it. When you learn to leverage your patience, you make the other person thirsty. 

Apply The Five-Year Rule. 

Timing in dealmaking is about keeping your cool. If things get tense, I always apply the five-year rule I learned from one of my mentors, Jonathan Wygant. 

Wygant, the founder of my talent agency, has a lot of wisdom about people, business, and deals. He always reminds me to consider one question when I am in the throes of a deal, dispute, or negotiation: “Will this matter in five years?” 

Specifically, is this thing that you disagree on today that’s causing you stress really going to make a difference five years from now? And the answer, many times, is, “No, it really doesn’t matter.” If it’s not going to matter then, why does it matter now? 

Thinking in the long term can help you avoid mistakes in the short term. Because it’s not just what you say that’s important. It’s also when you say it. What are some things you do to better time your deals? I’d love to hear it.