The End of Freestyle Negotiating

by Todd Caponi

June 23, 2026
Leadership
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Not a deal goes by without a discussion about the price.

My teams and I, and probably each one of you, have run into a wide range of buyer negotiating personalities:

The “I want it because that’s what we’re used to” negotiator.

The “sharpen the pencil” negotiator.

The “I’m an expert negotiator” negotiator.

The “I won’t take no for an answer” negotiator.

The “everything is too expensive” negotiator.

The “we’re a logo you should want” negotiator.

The “let’s crawl, walk, run” negotiator.

The “last-minute ambush” negotiator.

…and you can probably think of a hundred more.

The challenge for me earlier in my career was the feeling that every type of buyer negotiating personality required me to be a different person. And I sucked at it.

As a result, I ping-ponged through these conversations. For some, I became a defensive jackass. For others, I panicked. In most cases, playing games, being a jerk, or simply trying to make everyone happy led to longer deal cycles, eroded deal values, and a customer less confident that what I proposed held any truth.

While it may feel like every one of these negotiator types requires a different you, having a structure you can deliver and propose with confidence can make all of that go away.

Every B2B company’s business model is driven by 4 pricing levers:

  1. Volume.
  2. Timing of cash.
  3. Length of commitment.
  4. Timing of the deal.

Let’s take the “I want it because that’s what we’re used to” negotiator:

While running a sales team a few years ago, we were selling a solution with billing terms of “annual payments paid up front each year.” One of my representatives, while discussing this at the goal line with a decision-maker, wasn’t happy about it and wanted to talk to his manager… aka me.

When I got on the phone, she immediately started yelling. “You, and your entire company, are totally out of touch with the rest of the industry. Every vendor in this space bills monthly, and la-di-da along comes you making us pay the entire amount up front.”

It was her way of asking for monthly billing. So what did we do? Three steps:

1) Be Human: I started by saying, “Yes. You’re right. The rest of the industry does bill monthly. I’m assuming you and your organization greatly prefer to pay monthly instead of annually?” Then I listened…like a human.

2) Explain the Four Levers: “We’ve structured our pricing around four core elements. The primary driver is Volume, or how much of the solution you’re committing to. The second is the Timing of Cash, or how fast you pay. The third is the Length of Commitment to the solution. And the fourth is our mutual alignment around the Timing of the Deal.”

3) Walk them through, cards face up: The price you have is based on an annual, up-front payment. If you would prefer to pay monthly, you can, but we’re going to need to adjust something else to make up for it.”

She was disarmed. A conversation ensued. And in the end, she realized that even her own organization preferred a single payment during the year rather than twelve individual payments.

Negotiating doesn’t have to be difficult.

We’ve built a course around the Four Levers where you’ll learn a simple structure for how you deliver and propose your pricing. With that foundation set, you’ll learn how to use the Four Levers to confidently and transparently address every concession request you’ll ever hear, in a way that builds trust, maintains and even grows deal values, and shortens your sales cycles.

If you’re ready to easily master B2B sales negotiating in a way that you can take with you for the rest of your career, check it out and sign up:

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Todd Caponi
As it turns out, being transparent sells better, retains better, grows better and leads better. I speak (CSP®) and teach revenue organizations how human beings engage, prioritize, and decide, then how to use that knowledge (for good...not evil!) in their 𝐦𝐞𝐬𝐬𝐚𝐠𝐢𝐧𝐠, 𝐧𝐞𝐠𝐨𝐭𝐢𝐚𝐭𝐢𝐧𝐠, and 𝐫𝐞𝐯𝐞𝐧𝐮𝐞 𝐥𝐞𝐚𝐝𝐞𝐫𝐬𝐡𝐢𝐩. I wrote two award-winning books, 𝘛𝘩𝘦 𝘛𝘳𝘢𝘯𝘴𝘱𝘢𝘳𝘦𝘯𝘤𝘺 𝘚𝘢𝘭𝘦 and 𝘛𝘩𝘦 𝘛𝘳𝘢𝘯𝘴𝘱𝘢𝘳𝘦𝘯𝘵 𝘚𝘢𝘭𝘦𝘴 𝘓𝘦𝘢𝘥𝘦𝘳, with a third coming in January 2026 called 𝘍𝘰𝘶𝘳 𝘓𝘦𝘷𝘦𝘳𝘴 𝘕𝘦𝘨𝘰𝘵𝘪𝘢𝘵𝘪𝘯𝘨. I am a multi-time C-Level sales leader, a behavioral science and sales history nerd, and have led in seven roles including at two companies through successful exits, one with a double exit (IPO and a ~$3B acquisition).

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