
Jan 20, 2026
27
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"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.

