The orange story is a classic tale of negotiation.

Two kids both want the last orange. Instead of forcing them to split it, their mother asks a simple question: Why does each want it? One wants the juice. The other needs the peel for a cake. Problem solved—one gets the fruit, the other gets the peel.

It’s a memorable anecdote because it reveals a fundamental truth about negotiation: success doesn’t come from fighting for what you want. It comes from asking the right questions, and often requires reframing the conversation rather than doubling down on your position.

As CEO of Jotform for more than two decades, I’ve discovered that strong negotiators have a distinct competitive advantage. They secure better deals, navigate conflicts more smoothly, and build stronger relationships along the way. But the work of ensuring successful negotiations happens before the conversations even begin. ChatGPT can help you prepare for any negotiation, no matter how high the stakes. Here are some prompts to get started.

Identify What’s Really Driving Your Position

People tend to enter a negotiation knowing where they stand and the outcome they hope to achieve. But we rarely stop to consider what we fear losing. According to Scott Walker, a former Scotland Yard detective who spent 15 years as a kidnap negotiator, that’s an essential clarifying question.

“Going straight to what you fear the most, as painful as it may be, will increase self-awareness and help you manage any surprise emotions that could derail your talks, such as frustration, jealousy or anger,” he told the New York Times .

Maybe you’re afraid that letting one employee work from home will trigger an avalanche of similar requests. Or perhaps the fear runs deeper—that ceding ground will diminish your authority. Whatever it is, acknowledging that fear can help temper your emotions and clarify your thinking. Here’s a prompt to help you identify what’s really at stake before the negotiation begins.

“I’m preparing for a negotiation about [describe the situation]. I’d like you to help me identify what I may be afraid of losing in this conversation. Ask me questions that explore both practical concerns and deeper fears, including concerns about authority, fairness, relationships, reputation, finances, or future consequences. Then summarize the fears that may be influencing my position and suggest ways to address them constructively before the negotiation begins.”

See The Negotiation Through Their Eyes

Most people consider themselves empathetic. But passively considering someone else’s perspective is different from what I call active empathy—a deliberate effort to imagine yourself in someone else’s shoes.

“In order to gain another person’s cooperation, you first have to understand that person’s point of view, beliefs, and values,” explains Walker. Otherwise, push back is almost inevitable.

ChatGPT can help you practice this kind of active empathy, helping you understand different perspectives and reach solutions that satisfy both sides more quickly.

“I’m going into a negotiation and would like to better understand the other person’s perspective. I’m going to describe our [disagreement, negotiation, or difficult conversation]. Please help me practice active empathy by analyzing the other person’s likely goals, concerns, values, incentives, and fears. Here’s the situation: [describe situation].”

There is little satisfaction in steamrolling your fellow negotiator. If one side walks away feeling shortchanged, it can weaken the strength of the resolution, not to mention damage the ongoing relationship. What’s more, research shows that the most successful negotiators are just as invested in the other party’s success as they are in their own.

Years of experience have shown me that when you care about someone’s interests, they will make a greater effort to satisfy yours. As the orange story underscores, asking the right questions can help you identify solutions that are more straightforward than you might expect.

“I’m preparing for a negotiation about [describe subject]. My goal is [describe goal], and I believe the other party’s goal is [describe their likely goal]. Please analyze both sides’ interests and identify areas of overlap. Suggest three potential win-win outcomes that would create value for both parties, along with questions I can ask to better understand their priorities and find mutually beneficial solutions.”

Prepare For Their Toughest Objections

If anyone knows about navigating negotiations and reaching resolutions, it’s trial lawyers. One of the fundamental parts of trial preparation is anticipating objections and knowing how to answer them. Thinking on your toes is a valuable skill, but preparing ahead will inevitably strengthen your replies and help to quell anxiety about the unknowns.

You want to challenge your position before the meeting, not be ambushed during it. ChatGPT can help you prepare for inevitable objections.

“I’m going into a negotiation about [describe subject]. Here’s my position: [describe position]. Here’s what I know about the other party: [describe]. Challenge my assumptions, identify weaknesses in my argument, and list the strongest objections the other party is likely to raise. For each objection, suggest a thoughtful response and point out any areas where my position may need to be refined or further researched.”

Set The Tone Before The Negotiation Begins

It takes less than 1/10 of a second to assess someone’s face for factors like trustworthiness and dominance, according to research . Accurate or not, that first impression tends to inform our later judgments.

In the same vein, an opening offer can set the tone for a negotiation. Depending on the context, it’s probably not best to just read from a prepared statement. The conversation should be fluid. But gaining clarity on exactly what you want and what you’re ready to offer is key.

With the above points in mind—what’s at stake, potential objections, and whether there’s a win-win scenario—try this prompt:

“I’m preparing for a negotiation about [describe subject]. My ideal outcome is [describe ideal outcome]. My minimum acceptable outcome is [describe minimum outcome]. The other party is [describe other party], and their goals are [describe goals]. Based on this information, please draft an opening proposal.”

This, of course, is just a starting point. You’re tasked with editing the output and drafting the final version, ensuring that it’s in your voice, with your personal touch.