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Use AI as a high-stakes negotiation simulator. Feed it context about your deal and the other party, then have it embody their persona and negotiate with you. Crucially, after each round, prompt it to break character and provide expert feedback on your performance and what you gave away for free.
After a promising sales call, combat 'happy ears' by feeding your meeting notes into an AI. Ask it to identify the top three reasons the deal might *not* go through. This provides an unbiased third-party analysis, revealing red flags and potential objections you can address proactively.
Move beyond static scripts by using AI for dynamic sales training. Feed ChatGPT your call transcripts and common objections, then ask it to act as a specific buyer persona. Practice handling its objections in a role-playing chat, and conclude by asking it to provide a score and feedback on your performance.
Beyond automating repetitive tasks, AI's power lies in being a thought partner. Use it for an iterative, "ping pong style" back-and-forth to develop ideas, conduct deep market research, and rapidly get up to speed on new domains. This compresses the learning curve and leads to more nuanced strategies.
About 15% of buyers now feed sales proposals and terms into AI models, asking them to "poke holes in it." Salespeople must anticipate this by preparing for more technical negotiations, shoring up their own proposals, and understanding how AI might critique their offers.
Go beyond using AI for simple research. Feed it public data about a specific executive (from blogs, interviews, etc.) and instruct it to act as that person. This allows you to practice conversations, refine arguments, and master their specific communication style before a critical meeting.
Before a high-stakes meeting, train a large language model on transcripts of that executive's previous product reviews. You can then run your pitch or PRD through this custom AI to anticipate specific pushback, identify weaknesses in your proposal, and better prepare for the conversation.
Rehearse difficult conversations by having an AI adopt the persona of your boss, partner, or employee. This allows you to practice your approach, refine your messaging, and anticipate reactions in a safe environment, increasing your confidence and effectiveness for the real discussion.
Leverage AI to gain external perspectives without meetings. Prompt it to act as a specific persona—like a skeptical CEO, an enthusiastic user, or a New York Times reviewer—to critique your work. This reveals blind spots and strengthens your idea before sharing it.
Use prompting to access expertise you don't have and can't afford to hire. Instead of a generic prompt, instruct the AI to act as a specific, highly-credentialed expert (e.g., "an award-winning market strategist"). This effectively allows AI to fill gaps in your own skill set.
Starter Story's founder used ChatGPT to determine his ideal acquisition price before HubSpot's offer. This helped him negotiate authentically to a number he had pre-committed to, free from the emotional pressures and influence of the deal itself.