EP. 4

EP. 4

Building a Custom GPT for Every Rep on Your Team

Building a Custom GPT for Every Rep on Your Team

Jan 20, 2026

27

The conversation delves into the innovative use of AI in sales coaching, highlighting the challenges, benefits, and tactical approaches. It explores the impact of AI on sales coaching and the potential pitfalls to avoid. The role of AI in exposing coaching practices is also discussed, providing valuable insights for sales leaders and professionals. Takeaways Sales coaching with AI Differentiating coaching, training, and feedback Chapters 00:00 Transition into Sales and Coaching 06:36 Custom GPT for Sales Coaching 15:05 Impact of AI on Sales Coaching 23:41 Mistakes to Avoid in Implementing AI in Sales Coaching

The conversation delves into the innovative use of AI in sales coaching, highlighting the challenges, benefits, and tactical approaches. It explores the impact of AI on sales coaching and the potential pitfalls to avoid. The role of AI in exposing coaching practices is also discussed, providing valuable insights for sales leaders and professionals. Takeaways Sales coaching with AI Differentiating coaching, training, and feedback Chapters 00:00 Transition into Sales and Coaching 06:36 Custom GPT for Sales Coaching 15:05 Impact of AI on Sales Coaching 23:41 Mistakes to Avoid in Implementing AI in Sales Coaching

Guests:

Guests:

Rich Lane

Rich Lane

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Episode Summary

Episode Summary

"AI Will Expose the Managers Who Were Never Actually Coaching"

Most sales managers got promoted because they were the best AE—not because anyone taught them how to coach. Rich Lane, Head of Commercial at Kepler, has built a different approach: custom GPT projects for each of his reps loaded with his coaching philosophy, their deal transcripts, and every forecast call they've had together. In this episode, Rich walks through exactly how he preps for 1:1s by asking AI questions like "Did they identify the economic buyer?" and "What risk did the prospect mention that the rep might have missed?"—then turns it around on himself, uploading the coaching call transcript to ask "What would have made my coaching 10x better?" We get tactical on how reps can build mirror GPTs to prepare for their managers, why coaching and forecasting should be separate conversations, and Rich's hot take that AI won't replace sales leaders—it'll just expose the ones who were never really coaching in the first place.