Hacks & Hunches #1: Crushing High-Stakes Conversations with Gen AI

One of my favorite uses for Generative AI is to get better at crushing high-stakes conversations. Its ability to assume the perspective of another person—based on the context you provide—and to give feedback based on your desired outcome is, frankly, bonkers.

The trick? You must clearly define:

• the context of the conversation,

• the key attributes of the other person, and

• what a successful outcome looks like for both parties.

You can even prompt ChatGPT to generate a simulated dialogue between two people, tailored to their goals, personalities, and priorities.

As a strategy consultant, I’ve used this exact approach to prepare for (and crush) 30-minute meetings with 8 C-suite leaders at a global, multi-billion-dollar retailer—each representing a different function, from Finance and Marketing to Cybersecurity and Global E-Commerce.

Now imagine a college student preparing for their first job fair—about to meet recruiters from dozens of companies, with almost no experience in this kind of environment.

With a clear prompt, the right prep, and a vision for success, that student can walk in more confident, more prepared, and with dramatically better outcomes.

Got a high-stakes conversation coming up? Let’s show you how to use Gen AI to crush it.