I often return to a podcast episode from more than a decade ago about a meeting between an aspiring founder and a venture capitalist. In it, Gimlet Media founder Alex Blumberg meets with investor Chris Sacca to pitch his nascent podcast business.

For Blumberg, the meeting was pivotal. He realizes in real time how unprepared he was—both in terms of his footwear and his ability to pitch an investor. It’s candid, uncomfortable, and instantly resonates with anyone who’s ever walked out of a high-stakes meeting thinking: that could have gone much better.

Some lessons can only be learned through experience. Sacca was surprisingly gracious, and Blumberg walked away with valuable insights. But today’s founders have tools like ChatGPT at their fingertips to help them prepare for high-stakes conversations in advance—saving those hard-earned lessons for the things no one can anticipate. Here are five prompts to get started.

Know What You Want From The Meeting

At Jotform, my team knows that my door is always open for meetings. My only request is that people show up knowing what they want to achieve. If you want to share an idea, be ready to talk about how you envision implementing it. If there’s an issue, try to offer your ideal solution. I aim to do the same when prepping for meetings.

One of the reasons that meetings have been maligned as unnecessary and time-wasting is that too often, we show up without a clear idea of our goals for the meeting. ChatGPT can help.

“I’m preparing for a meeting about [topic/situation] with [person/team/organization]. I’d like you to help me clarify my top goal[s] for the conversation, the outcomes I should prioritize, and the next steps I want to leave the meeting with.”

Nail The First 40 Seconds

Today’s elevator pitch has to be tighter than ever. Consider this: researchers have found that the average attention span has shrunk to a mere 40 seconds . That’s barely enough time for an elevator ride to a low floor, which means you need to capture attention quickly and communicate the essentials even faster.

A strong opening should cover three things: what your idea is, why it matters, and why you’re the right person to bring it to life.

For example, imagine you’re launching a service that helps busy families coordinate care for aging parents. Your pitch might sound like this: “Millions of adults are juggling work, kids, and the growing responsibility of caring for aging parents, but most families are still managing appointments, medications, and schedules through one-off texts and spreadsheets. After helping coordinate care for my own father, I built a platform that gives families one place to organize everything and stay informed. We’ve already tested it with local caregiver groups, and families are willing to pay for tools that reduce stress and save time.”

Whether it’s a new venture or a solution within an existing organization, the formula is simple: the what, the why, and why now. And it’s easy to practice and replicate with ChatGPT.

“I’d like you to help me craft a concise, compelling pitch for [idea/project/initiative]. The audience is [investors/executives/team members/etc.]. Please help me create a version under 60 seconds in a conversational style. Make sure each version clearly explains what the idea is, why it matters now, and why [I/our team/our organization] is uniquely positioned to execute it. Please also ask any questions you need to gather the relevant details before drafting the pitch.”

Do Your Homework Before You Walk In

One of Blumberg’s funnier admissions during the podcast episode is that he didn’t really know who Chris Sacca was—how much of a big deal he was in the industry. It’s smart practice to research whomever you’re meeting with and become an expert on the subject matter—or at least have a strong grasp on the relevant information.

It’s no secret that ChatGPT isn’t the most reliable source on its own. It still regularly “hallucinates”—generating inaccurate information or overstating the facts—a wrinkle that doesn’t seem to be going away any time soon. However, it can be a powerful tool for identifying relevant reading sources. (And can also synthesize that reading if you prompt it to.) Here’s a prompt to get the research engine running:

“I’m preparing for a meeting with [person/company/organization] about [topic]. Please help me identify the most important background information I should know before the meeting. Include relevant personal or organizational history, recent developments, industry trends I should understand, and questions I should research further using reliable external sources.”

Prepare For The Questions You Hope They Don’t Ask

It’s a bit like Murphy’s law: if something can go wrong, it will. And the one question you didn’t prepare for in a meeting is always the one they ask.

As a leader, it’s hard to think of a worse feeling than feeling like a deer in the headlights during a high-stakes meeting.

ChatGPT can help you prepare for the likely questions, as well as the less obvious ones that you should prepare for just in case.

“I’m preparing for a meeting about [topic/proposal/decision] with [audience]. Please act like a skeptical [investor/executive/client/etc] and generate questions I’m likely to face, including difficult or unexpected ones. After each question, suggest the main points a strong answer should include, along with any follow-up questions I should prepare for.”

Check Your Mindset Before The Meeting Starts

As much as we prepare, meetings won’t always go as we hoped. Parties have different objectives and motivations. Perspectives differ. Ideas clash. At Jotform, that diversity of opinions is something we welcome. I’ve found that despite the discomfort of friction, it ultimately leads to better, more reasoned, more innovative solutions.

But it’s essential to go into a meeting with an open mind. To cultivate that headspace, author and founder Jeff Wetzler recommends running a quick “ curiosity check .” To paraphrase, it goes like this: Before an important conversation, pause to identify your current mindset, set an intention for how open and receptive you want to be, and consider what the other person may be thinking, feeling, or struggling with that you can’t yet see.

With this kind of self-awareness, the outcome is bound to be more satisfying to all parties, regardless of how strongly you may disagree. Here’s a prompt you can use with ChatGPT to conduct your own curiosity check.

“I’m preparing for an important conversation. Please ask me questions to help me identify the mindset I’m bringing into this discussion, the assumptions or blind spots I may have, and what the other person could be thinking, feeling, or struggling with that I’m not considering. Then, please ask additional questions that help me move into a more curious, open, and constructive mindset before the conversation begins.”