The 21 Hats Morning Report

The 21 Hats Morning Report

AI Can Make You a Better Negotiator

For example, you can use it for background research and to brainstorm arguments. You can even use the voice function for rehearsal.

Loren Feldman's avatar
Loren Feldman
Oct 20, 2025
∙ Paid

Good Morning!

Here are today’s highlights:

  • If the ACA subsidies go away, small businesses will take another big hit.

  • Of course, health insurance isn’t the only insurance category generating huge rate increases.

  • Here’s how one company found an untapped source of labor in rural America.

  • Small businesses say they can survive the tariffs so long as their customers pay higher prices.

EDITOR’S NOTE

This week’s Dashboard podcast will be published on Friday instead of Monday: We here at 21 Hats hope you can still have a productive week.

ARTIFICIAL INTELLIGENCE

Here’s how AI can make you a better negotiator: “Earlier this year, Jennifer Barnes received an email from a client in financial distress, asking to renegotiate their contract. As the founder and CEO of Optima Office, an outsourced HR and business services company based in San Diego, this was not the first time she’d received a message like this. She’s been in business since 2018, growing her 100‑employee company to around $18 million in revenue and earning a place on the Inc. 5000. There isn’t much she hasn’t seen. From experience, Barnes knew negotiating was going to burn the better part of an hour. First, she’d have to read the whole exchange. Then she’d think about how to respond. After that, she’d have to spend a lot of time writing and editing the response.”

  • “This time, however, instead of working through it on her own, Barnes popped the email into her paid version of the AI chatbot Claude and asked it for a three‑point summary of the client’s demands. She then uploaded a brief synopsis of her perspective on the situation, did a light edit, and hit send. Total time to craft the message that solved the problem? Five minutes.”

  • “As an entrepreneur, it can feel like you’re constantly either preparing, actually doing, or managing the results of a negotiation. All of that is intellectually and emotionally demanding, says Emily DeJeu, professor at the Tepper Business School at Carnegie Mellon University, who teaches classes on negotiation. ‘Even in our textual exchanges, negotiation is happening as much with our guts as with our brains.’ But with the advent of AI, using your own brain unassisted has become a bit passé.”

  • “[Sesh Iyer, North America chair of BCG X, the tech build-and-design unit of Boston Consulting Group] suggests starting with what you have right now. It’s easy enough to incorporate AI into negotiation prep with the tech your business probably already uses. Test it out with background research, brainstorming arguments and counterarguments, and use the voice function for rehearsal.” READ MORE

User's avatar

Continue reading this post for free, courtesy of Loren Feldman.

Or purchase a paid subscription.
© 2026 Loren Feldman · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture