How Sales Leaders Can Use ChatGPT Roleplay to Fix Sales Training Fails and Boost Cold Call Wins

Sales reps don’t get enough reps—and it’s killing performance. Kelly and guest Jeff Bajorek show how ChatGPT can simulate high-stakes cold calls and discovery sessions so your team doesn’t practice on prospects.

Three out of four salespeople are failing. Why? Because most sales training stops short of actual practice. In this episode, Kelly is joined again by Jeff Bajorek to demonstrate a live, unscripted roleplay using ChatGPT. No scripts, no retakes—just real-time practice that mirrors the real world.

They start with a cold call simulation and then shift into a face-to-face discovery meeting, each designed to uncover and overcome the two big obstacles every sales team faces: lack of pipeline and stalled deals. You’ll hear exactly how ChatGPT can be used to rehearse permission-based openers, work through objections, and tailor questions based on buyer psychology.

You’ll also hear how to level up AI roleplay sessions with contextual prompts from real earnings calls or buyer research, and why this approach beats traditional practice methods—hands down.

This isn’t theory. It’s tactical, repeatable, and ready to use. If you're managing a sales team or trying to sharpen your own skills, this is the episode you didn’t know you needed.

Follow the audio podcast and watch OR listen wherever you are: https://linktr.ee/salesuntraining   Kelly Riggs is an author, speaker, and business consultant for executives and companies throughout the United States and Canada. He has written two books: 1-on-1 Management: What Every Great Manager Knows That You Don’t and Quit Whining and Start SELLING! A Step-by-Step Guide to a Hall of Fame Career in Sales. 

Get more Kelly: www.BizLockerRoom.com. 

Widely recognized as a powerful speaker and performance coach in the areas of sales, management leadership, and strategic planning, Kelly is a former sales executive, a two-time national Salesperson-of-the-Year, a business owner, and a member of the Forbes’ Coaches Council since 2019. 

Music and Editing by Pod About It Productions @dougbranson