5 Ways to Keep Improving Your Negotiation Skills

My youngest heads back to college this month to finish her senior year. I can’t believe how quickly time’s gone by. Back-to-school has always been a marker for me and a good place for reflection. This year, I keep hearing a line from an old mentor of mine: “If you know everything, you’ll never grow.”

She said that to me after my first Scotwork class, more than 20 years ago. I was the guy in the back row with my arms folded, daring her to teach me something I didn’t already know. I’d been closing deals for years, so I figured I was there to have my talents validated.

It took less than an hour for me to realize I knew nothing about negotiating. I thought about how I won those deals: intimidation, pressure, and cheap tactics. Even though I won deals, I started to see all the money left on the table and the damaged relationships because I wasn’t actually negotiating. It was humbling, and my instructor handled it in a way that made me feel safe to be wrong.

My mentor had seen the pattern before I did: My certainty was so complete that other perspectives couldn’t get in, and early in my career, I was terrified of appearing anything less than capable. Between my arrogance and insecurity, there was no room left to learn anything.

Turns out, my attitude wasn’t unusual: Resistance to learning is a pretty standard human setting. We take comfort in routine and predictability, and learning requires walking into the unknown, which most people would rather avoid.

Here’s why that matters for anyone who negotiates for a living: Negotiation isn’t a skill you acquire once and own forever. It’s perishable. It requires regular use and adjustment to stay sharp. I was convinced I didn’t need to grow, so my skills had regressed. I never tried anything new at the table. When a deal went sideways, I blamed the other side instead of examining my own moves. I wrote off every chance to get better as time I didn’t have. My hubris didn’t just stall me; it made me a worse negotiator.

When my mentor held up the mirror, it changed how I learn. Here are 5 techniques that I continually use . . .

1. Name what you don’t know. When you encounter a negotiation situation that you struggle with, call it out. Recognizing the gaps makes the next steps much easier.
2. Ask for help. Negotiation is a human skill, so the best learning happens through interaction, discussion, and repetition. You can read a book, listen to a podcast, or ask AI, but none of that replaces working on your negotiation skills with someone who actually does it.
3. Reflect on the deals you won, not just the ones you lost. This isn’t about blame; it’s about examination. A deal that closed on your first offer will have as much to teach you as the one that fell apart. Look at both.
4. Get feedback from someone who watched you negotiate. Have a colleague sit in on the call or the meeting and tell you what they saw. Your own read on your performance is exactly where your blind spots live.
5. Write the plan down. Document what you want to improve about your negotiations, how you’ll get there, and the support you’ll need. Plans change as you go, and that’s fine. You’re still far more likely to get somewhere with one than without.

As back-to-school season arrives, I’d encourage you to go back to school, too. Learn something new. Close a gap you’ve been carefully working around. And if you negotiate for a living, take perishability seriously, because the skills you neglect this year show up as concessions next year.

If you know everything, you’ll never grow. And in this business, not growing costs you money.

Negotiation Training and Consulting to Help You Keep Improving Your Negotiation Skills.

Negotiation isn’t a skill you acquire once and own forever. It requires regular use and adjustment to stay sharp. Rely on Scotwork’s expertise to keep your edge.

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