The embarrassingly stupid sales mistake even smart negotiators make—And my foolproof method for avoiding it

Let me tell you a story about a friend of mine. We’ll call him Alexander.

Alexander was working with one of his company’s best clients—a high-value, long-term customer. That client was evaluating alternatives and considering leaving the company for a new vendor. Alexander had been negotiating with them for a few weeks, trying to keep them around.

I was serving as an advisor and helping him out with the process. He would call me up after his interactions with the client and let me know how things were going. I’d give him some advice each time, and he’d keep me in the loop.

At the beginning of the process, the client was 99% sure they would change to a competitor. We eventually moved them to 50/50, and even 60/40 in favor of Alexander’s company. I was sure they were going to stay on.

You might not have a seasoned startup CEO as a personal advisor by your side, but you can get a free copy of my book on negotiating better deals.

Then, today, Alexander called me with a confession. “Steli,” he said, “I think I made a big mistake.”

Even veterans make rookie mistakes

It’s worth noting here that Alexander is an experienced salesperson. He’s not new to this game. But he was under a lot of pressure. And that’s when people make mistakes.

He’d been going through this negotiation for weeks. He had other things to get done. He was tired of working with this client day in and day out. And he was under pressure to keep a valuable client on board.

Even veterans make easy-to-avoid mistakes when they’re under pressure. Sales negotiation is about avoiding dumb mistakes. It’s not just about doing everything right and getting the sale. It’s also about avoiding mistakes that make you facepalm when you see how easily they could have been avoided.

That’s the kind of mistake Alexander made. Here’s what happened:

Alexander had an in-person meeting with the client a while back. And in that meeting, he told the client that some customers who had left his company for other vendors had run into painful difficulties. Integration, implementation, pricing, and transitions had all been a source of serious headaches.

The day after the meeting, the client called and asked if they could get in touch with one of the companies that had gone through these difficulties.

Alexander knew he should think about this request carefully, but he was distracted. He gave it some thought while he was going through his email and doing other daily tasks.

He didn’t call me.

Instead, he thought of a company that had transitioned away from his, figured they’d be a pretty good reference, and made the introduction.

Then today, he learned that his company’s client was flying out to visit the ex-customer at their home office.

As soon as he told me that, I knew the deal was almost certainly lost. Why would they be flying out there if not to ask about things like tips on how to make the transition go more smoothly? Or to connect with the ex-customer’s consultants? Or get suggestions on which vendors to look into?

Alexander was so close to closing the deal, and he threw it away.

He should have talked to the ex-customer to set expectations, find out what they would say when asked about the transition, and see what they would recommend to his current client. He needed to be in control of the message—and probably should have also been on the call. (Despite these requirements, sharing references is a great tactic if you do it right.)

Now all he can do is call the ex-customer to ask about how the conversation went and why his client is flying out to their office.

This was a big mistake. Even the smartest people—like Alexander—make dumb mistakes under pressure.

How to not screw up your deals

Pressure comes from things like high-value deals, long negotiations, and high quotas. But you might feel pressured for any number of reasons. There are two things you need to do when you’re negotiating under pressure:

First, use an external advisor to check yourself. It might be a friend with sales experience. It could be someone else at your company. There are just three requirements: that advisor needs to be honest, sharp, and not invested in the deal.

That means you can use an engineer, a project manager, or an administrative assistant at your company. If you trust their wits and they’re not involved in the deal, they’ll make a good advisor.

The further along you are in the negotiation, the more crucial this is. During a grueling negotiation, you can’t trust yourself to think rationally. You’re emotionally invested, you’re exhausted, and you’re under pressure. That’s when you make mistakes.

Second, you need to be completely transparent with that advisor. Don’t do anything without talking to them about it first.

This is especially important if you feel uncomfortable about a particular idea or tactic. If you think your advisor will say “no,” be doubly sure to talk to them. If you’re uncomfortable, you’re probably about to make a mistake.

No matter how senior you are—whether you’re a brand-new salesperson or the CEO of a company—you need to talk to your advisor before making a decision.

I do it myself. Two years ago, I had a big negotiation with one of our clients, and I bounced a lot of ideas off my technical cofounder. He has no training or authority in sales—but he’s a smart guy and very honest. I used him as a sounding board almost every day.

I was feeling impatient. I just wanted to get the deal done and move on. But I knew that I couldn’t trust myself, because I was under pressure and prone to making a terrible mistake.

But with my cofounder’s help, I avoided making a mistake and kept the client onboard.

Check yourself

It’s easy to think that you won’t make a dumb mistake. Whether you’re a salesperson, a sales manager, or an executive, you think your experience will prevent you from doing something like Alexander. But trust me: when the pressure’s on, you will make a mistake.

So find someone to talk to about your sales negotiation, and be totally upfront with them. It will save you lost sales and a whole lot of headaches.

Want more tips on negotiating better deals? I've written an entire book on the subject, and you can claim your free copy here!

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