PROMPT This AI Challenge

"From Skill Agents to Digital Personas - Building Smarter Sales Systems" featuring Ben Taft 

Every episode of the PROMPT This podcast includes an AI Challenge for the audience.  Follow the instructions below to complete this episode's challenge.

If you want to sell better, stop pitching and start listening. This challenge flips your prep from product-first to customer-first by turning AI into the voice of your most successful clients.

You’ll walk away with something most teams only dream of—a living, conversational knowledge base that captures what your best customers actually care about.

Step 1: Upload Your Case Study

Go to ChatGPT and start a new chat with one of your company’s customer success stories by uploading a case study file to the prompt window. Then, turn on Voice Mode and begin a conversation with the AI as if it is your client.

Example prompt:

“Train yourself on this case study about how Acme Co. improved supply chain visibility using our analytics platform. Speak as if you are the operations leader from that project.”

The more context you feed it—metrics, team dynamics, emotional wins—the more human and insightful the conversation becomes.

Step 2: Interview the Case Study

Next, shift the perspective. Use ChatGPT to interview your customer success story just as you would in a discovery call. Ask open-ended questions that surface emotion, value, and motivation.

Try questions like:

• “What was your biggest pain before using our solution?”

• “What specific outcomes mattered most to your team?”

• “What nearly stopped you from buying?”

• “What advice would you give to others considering this product?”

These answers give you the language real customers use—the emotional hooks, the credible objections, and the natural phrasing that make your future content sound authentic.

Final Thought

The future of sales enablement isn’t just automation—it’s AI empathy. When your digital systems begin to speak your customers’ language, your team learns to listen more deeply, connect more meaningfully, and build trust at scale. This challenge isn’t about replacing human understanding—it’s about amplifying it.