Use AI to negotiate smarter
Ask AI to role-play the other side. Ask it to break apart your argument to make it stronger.
Note: This was originally posted on LinkedIn.
// 10X Productivity as an AI-Native Lawyer
Use AI to negotiate smarter: Ask AI to role-play the other side. Ask it to break apart your argument to make it stronger.
Looking back, I wished majoring in philosophy had more practical life ROI (besides being junior bootcamp for law school). But those seminars taught me a negotiation tenet I still use to this day.
Be charitable. Assume the steel man i.e. the strongest good-faith version of the other side’s viewpoint. My argument is strongest when I can understand – and overcome – that steel man.
For example, say you want to make a counter-proposal at a key negotiation next week. Ask AI: “Pretend you’re my counterparty. What do you think about my terms? How will they help or hurt you?”
Ask further: “Tell me your strongest arguments against it. What are my best counter-arguments? Be brutally honest. Show me your lines of reasoning.”
AI is a 24/7 sparring partner to pressure test negotiation strategies big and small. You can test out different ways to frame a topic, a new line of reasoning, down to the best phrasing for a talking point.
Better yet, AI can do this for any part of working life.
Say you’re pitching a client. Ask AI: “What do you think is my firm’s biggest value-add and weakness for this matter, compared to my competition?”
Or say you’re briefing a regulator. Ask AI: “Look at their press releases and public interviews. What are their enforcement priorities? How is my client most vulnerable? What will the regulator think about XYZ defense, and how can I preempt those questions?”
AI can role play as your business partners, your opposing counsel, your press critics. Even your boss or the partner reviewing your work.
This can be as fast as running an AI spot check before you ship an email, or getting a few hours of intensive personalized prep before a big meeting.
Yes, AI’s reasoning isn’t always perfect. But negotiation is a game of inches. Every bit of leverage helps, and AI can equip you with just a few more tools before you head into that next opportunity.
The key is to give AI enough context on the other party so it knows about their background and goals, which I’ll write more about next week.