One myth that dealmaking gurus, books, and even master classes get you to believe is that you can make great deals 100 percent of the time—if you just learn a few tips and practices. Sign up here and be the master negotiator! Unfortunately, that’s hype and not reality.

I say this without judgment: Some of those gurus are my clients, and I even teach some of those classes.  

Here’s the rub. I used to think I was such a good dealmaker that I could convince anybody. And if someone wasn’t convinced, I just needed to work harder. If the deal still didn’t work, then it was all their fault, their loss—end of story.

The more I tried, the more I became frustrated. I would spin my wheels, only to learn the deal had gone to someone else. Then—after years of therapy, coaching, the Hoffman Process healing retreat, and a lot of higher-ed—I had an epiphany.

What I’ve learned over the years, and after collaborating with the best deal makers in the world, is that the next best way to win a deal is to walk away when the current deal isn’t working. 

For the past 20 years, as a talent agent, dealmaker, and media attorney, I’ve been teaching people how to negotiate deals. I even teach a &Then masterclass on dealmaking. This is the method I use to concentrate on the deals that will work and let go of the ways that aren’t working.

Two ways to win a deal

My good friend and major tech founder, Pat Sullivan, summed up the dealmaking philosophy best. 

For dealmaking, “There are two winners in every deal. The first guy who gets the deal—and the next guy in line who knows he’s not going to get the deal, so he moves on to close another deal!”

This is your best strategic move—for two reasons:

  • The deal isn’t working. Get out there and find a new one that will. Maybe you’ll even do better.
  • Walking away might call the other person’s bluff and make them reconsider. They might be so afraid they’ll lose out on your business that they reach out and close the deal.

Either way, you’re a winner. Here are the four signals that indicate it’s time to walk away:

1. No good answers—they’re being evasive.

If your client can’t answer the who, what, or when—as in who needs to be involved in major decisions, what are the key deliverables, and when the project needs to be completed—then it’s time to hit the road.

2. No reply at all—you’ve been ghosted.

Have you called, emailed, texted—and still no reply? Chances are, when your prospect goes dark, they aren’t just too busy to answer your query. They aren’t interested in making a deal. It’s best to move on.

3. No money—they have money in their mouth and not in their pocket.

Prospects will always say contracts are too expensive. However, when it becomes clear the prospect doesn’t truly have the budget to work with you, politely steer them toward someone with a lower-priced offering. Then, find someone who does meet your budget.

4. No stability—they didn’t have the authority or the ability to close the deal.

If your prospect is constantly requesting changes in the terms or amounts you originally discussed, chances are they don’t have a clear vision of what they really want. Politely say you don’t believe your product or service is right for their current needs. Then tell them you would be happy to work with them in the future. 

Remember, you can always make a deal. It just may not be with the prospect you’re currently working with. You need to know when to move on so you can find someone who wants to make a deal.

Good luck, and let me know how this works for you.

This article was originally published by Inc. Feb 9, 2025.