How to use an LLM to prep for a high-stakes meeting
Whether it's a media interview, a board presentation, a pitch to a major donor, or a negotiation with a potential partner, it can be hard to know how to handle high-stakes meetings.
What if you had a coach with unlimited patience who could help you refine your pitch, anticipate tough questions, practice your responses, and role-play challenging scenarios?
You can use an LLM for that!
Of course, you can use the LLM to extract insights from any meeting prep materials:
“I am a [role] and going into a meeting with [other parties] on [topic]. I am hoping to [goal]. Can you summarize [documents] for me?”
Adding context may seem irrelevant for a summary task, but try it with and without! You’ll often get focus on the key points that you can use from your role to achieve your goal.
Useful, right? But I can do you one better.
Building Personality Profiles for Better Strategy
For meetings with people you know well, try creating detailed personality profiles first:
"I am going to have a meeting with [person] who is [role]. I would like you to give me some advice about how to deal with them in a [type of meeting]. First, please build a personality profile of them. Ask me some questions that will help you get to know them."
You can even specify a personality framework if you're familiar with one:
"Please build a profile using the Five Factor model of personality" (or DISC, Myers-Briggs, etc.)
The AI will ask targeted questions about the person's communication style, decision-making patterns, priorities, and pet peeves. As you answer, you'll likely realize things about this person that you hadn't consciously considered before.
It will spit out an OK personality profile for you. Tweak it: you can ask for direct changes, or tell it a story about their behavior and ask it to update the profile accordingly. As always, if it gets stuck on something up helpful, you can bring what is working to a new chat and start over.
Once you have profiles for all the relevant people, you can upload them as context for this and future meetings with them. Creating a little committee of your executive team, board, or other group you regularly present to can be a game-changer.
Let it get to know you, too
Tell it about your strengths and weaknesses in this context to help you prepare. What are you most worried about getting in your way for this meeting? For example:
“I am confident I can help, but I can get in my head if I feel like I am trying to sell something”
“I tend toward a scarcity mindset and need help seeing ways to grow the pie.”
“I tend to focus on what they want and forget my goals in the moment.”
“I can get conservative early and fail to think big.”
You can of course have it interview you to build a personality profile. If you don’t want it to remember what it learns about you for future chats, turn off chat history and training, or whatever the model you use calls the setting for learning across chats.
Some people who do this kind of relationship work with their LLM, though, do the opposite: they put their own personality profile in custom instructions so that it always takes them into account. Maybe try this after you’ve used your model a few times for relationship questions if you are getting great results.
Putting It All Together: Role-Playing Your Success
Once you've built comprehensive profiles, start a new chat and use all that context for specific preparation tasks:
Start with rich context:
"I am [role] in [organization]. I am preparing for a meeting with [person or group’s role]. My goal is [specific objective]. I am most worried about [specific concern] and [additional worry]. A satisfactory outcome would look like [result.] An ideal outcome would look like [better result]. The thing I most want to avoid is [worst result]."
+ Preview your task:
“I would like help with [specific task.]”
Here are some examples of tasks you might request help with. You can always add more requests in the same chat to preserve context from the previous.
Practice your pitch: "Please act as [person] and evaluate my proposal. Push back on weak points and ask the questions they're most likely to ask."
Anticipate objections: "What are the top 5 concerns [person] is likely to have about my proposal, and how should I address each one?"
Navigate difficult dynamics: "Help me role-play this negotiation, keeping in mind that [person A] tends to be very direct while [person B] avoids conflict."
+ Then, let AI interview you:
"Before we begin, please ask me some questions that will help you give me the most useful answer. Please give me these questions one at a time and consider my answers when you [specific task you want help with]."
This approach works because it forces you to articulate your real concerns (not just the "official" ones) and helps AI understand the nuanced context, including aspects of the context you didn’t think to add.
Real-World Applications
Try this method for high-stakes interactions:
Media interviews: Practice handling tough questions and staying on message
Job interviews. Get comfortable pitching yourself and get unlimited practice and feedback
Board presentations: Anticipate concerns from different board member personalities
Donor meetings: Tailor your approach to individual giving motivations
Performance reviews: Prepare responses that align with your manager's communication style
Partnership negotiations: Understand the other party's priorities and constraints
Important Caveats
While AI can be incredibly helpful for meeting preparation, watch out for these pitfalls:
Over-confidence: Some AI models are "sycophantic"—they'll tell you what you want to hear rather than giving honest feedback. Always ask for constructive criticism explicitly. This may take some tweaking to find the right prompt for this. One of the hosts on the useful podcast “Beyond the Prompt” uses something like “Cold-war era Soviet Olympic judge.” That’s a bit on the harsh side for me!
Missing nuance: AI might overlook important power dynamics, cultural considerations, or industry-specific norms that could affect your meeting. Double check your context to make sure you’ve got this important context in there, especially if its advice feels off to you.
Generic strategies: Make sure the advice fits your personality and role. AI might suggest approaches that work in theory but feel inauthentic when you try to execute them.
Your Next Steps
The next time you have an important meeting on your calendar, try this method.
Block out 30-45 minutes for AI-assisted preparation
Let AI interview you about the people and situation before jumping in to the task
Use the insights to practice specific scenarios
See how it feels. Did it help? What worked, and what do else do you want to try?
Remember: the goal isn't to script every moment of your meeting, but to think through the dynamics, anticipate challenges, and practice your responses. When you've done that kind of deep preparation, you can focus on being present and authentic in the actual conversation.
Did you find this helpful? This is just one example of advanced prompting guidance available as part of your free Mission-First AI Starter Kit!
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LLM disclosure: this was a short one!
”Can you draft a blog post based on this content I wrote?”
It required more editing than I’d like, so I need to listen to my own advice and add more context!
Then, “Can you create a small square image as a cover for this blog post?”
ChatGPT added its own logo! What a surprise!