A teammate pings you: “Can you jump on a quick call? The vendor wants to revisit pricing.” Or your manager says: “We need to realign responsibilities on this project.” You have 30 minutes, you feel the tension, and you can tell there is more you should be negotiating, but you are not sure what. This is a moment when generative AI (like ChatGPT, Claude, Gemini, or Copilot) can help. Don’t think of AI as giving you a script or telling you what to do. Think of it as acting like a fast prep analyst that helps you get clarity, expand your options, and walk in with better questions.
My simple frame is: THINK, BE CURIOUS, then ASK.
What AI is good for (and not)
AI is most helpful before the conversation. It can help you clarify what you want, surface tradeoffs, generate proposals, and practice how you want to show up. It is a thinking partner, not a decision maker. You still have to do the human work of reading the room and building credibility. But it can help you get ready.
Try This: Copy and paste (THINK, BE CURIOUS, ASK)
Use an organization-approved tool if you have one. Do not paste confidential information. Anonymize names, clients, numbers, and internal details. Start by pasting answers to these questions in your prompt:
SITUATION inputs (paste this first):
My role:
Their role:
Relationship context (new, ongoing, strained, high trust):
What I think I am negotiating about:
What I want:
What I can offer:
Constraints (timing, budget, policy, approvals):
THINK: “Ask me 5 clarifying questions. Then restate my goals as a ranked list across outcomes, relationship, timing, and risk. Next, identify my top 2 must-haves, my nice-to-haves, and what I should not concede. Then propose 8 possible tradeoffs or concessions that would cost me relatively little but could matter to them, and for each one, explain why it might be valuable to the other side.”
BE CURIOUS: “Separate the facts from the story I am telling myself. Then list 5 plausible interpretations of the other party’s behavior that do not assume bad intent. For each interpretation, give me one question to test it. Finally, write 10 high-leverage questions that sound natural: 3 opening questions, 3 diagnostic questions (constraints, approvals, timing), 2 assumption-testing questions, and 2 alignment-check questions before we close.”
ASK: “Help me build a flexible offer menu for this negotiation so I can stay present and respond in the moment. Create 3 package options (A, B, C) that reflect different priorities. For each package, include: what I could ask for, what I could offer, and the underlying interest it might meet for them. Then give me: 5 curiosity questions to ask before I propose anything, 3 simple ‘bridge phrases’ that sound like something a real person would say to keep the conversation collaborative and exploratory, and one rule of thumb for when to shift from exploring to proposing. Do not write a script. Keep everything short, natural, and adaptable.”
Three guardrails that keep AI helpful
Treat outputs as hypotheses, not answers. Ask: “What assumptions are you making, and what information would change your recommendation?”
Use AI to generate options and questions, then speak like yourself.
Use AI to THINK clearly and to generate questions that support curiosity, but then put it away. In the conversation, what counts is clear objectives, genuine listening, and how you handle the moment when things get tense. Trust is built through accountability and follow-through, not perfect phrasing.
Optional: The 10-minute debrief (after the negotiation)
Right after the conversation, jot a few bullets: what was said, what you inferred, what felt tense, and what you agreed to. Then use AI to debrief and sharpen your next move. If this is an ongoing relationship, capture one clear follow-up: who is doing what by when. A simple running note of commitments and dates helps you follow through and build trust over time.
DEBRIEF: “Here are my notes from the conversation (bullets): [paste]. Identify the turning points, what information I missed, what I inferred versus what was said, and two alternative responses I could try next time that still sound like me. Then draft a short follow-up message that confirms next steps in a warm, professional tone.”
Use AI to prepare and practice. It is your job to THINK, BE CURIOUS, and then ASK.