PROMPT This AI Challenge
Episode 5: “The AI Shift - How Companies Start, Scale, and Rethink Work” featuring Jason Green
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’re in sales, you know the golden rule: objections aren’t rejection, they’re opportunity. But most sales teams don’t practice handling objections until they’re live with the prospect. That’s like learning to swim when you’ve already jumped in the pool.
This week’s guest, Jason Green, described the various ways he is seeing companies get started with AI including using it to practice objection handling by a sales prospect. This AI Challenge shows you how to use ChatGPT along with Voice Mode, a conversational voice interface, to rehearse tough sales moments.
We’ll use a real-world scenario: inviting a guest onto the Prompt This podcast.
The Setup
Imagine you’re trying to book a guest. You have your pitch ready:
“We’d love to feature your story on the Prompt This podcast. It’s all about real leaders experimenting with AI and driving business growth.”
Now the guest responds with hesitation. This is where most reps stumble. Instead, you’ll turn to ChatGPT.
Common Objections You’ll Face
Guests might say:
- “I don’t have the time.”
- “I’m not sure this will reach my audience.”
- “I don’t feel comfortable speaking publicly.”
- “I need to check with my team first.”
- “What’s the ROI for me?”
These are objections that map directly to what sales teams hear daily across industries: time, relevance, confidence, authority, and value.
Using ChatGPT to Navigate Objections
You’re going to use ChatGPT for this exercise including Voice Mode.
Step 1 - Log into ChatGPT: If you don’t have a ChatGPT account, sign up now.
Step 2 - Enter voice mode: Click on the “use voice mode” icon in far right of the “Ask anything” text input bar. This activates the interactive AI agent for ChatGPT. Now you can just start talking with the AI.
Step 3 - Supply context: Before describing the objections below, read the following to set the stage.
“I am the producer for the Prompt This podcast. I am contacting potential guests about joining the show but am running into a bit of pushback.
Our typical guests are operators, builders, and thinkers—real business executives who have begun deploying AI in their business or for their clients. By sharing their experiences in a simple one hour interview, our guests get visibility for their company and build their own personal brand as a thought leader.
Guide me through handling common objections.”
Practicing in Real Time
The power of ChatGPT’s conversational voice mode is you can roleplay in the car, at your desk, or on a walk. Practice objections out loud, hear responses instantly, and refine your delivery. It’s like having a 24/7 sales trainer with infinite patience.
Final Thought
Objection handling is the difference between good salespeople and great ones. Using ChatGPT’s conversational voice interface gives you a private gym to build those muscles. The next time a customer—or a podcast guest—hesitates, you’ll know exactly how to listen, respond, and turn hesitation into a yes.
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