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Most coaching goes wrong before the coaching conversation even starts. If we only review a tiny sample of calls, chats, or tickets, we end up “coaching the seventh hole” and missing the real issue that shows up earlier in the customer journey, like unclear expectation setting or a pattern that repeats across channels.

I’m joined by Rob Dwyer, Senior Technical Account Manager at Level AI and CX Executive in Residence, to unpack how AI can identify coaching opportunities without pretending to replace leadership. We use a surprisingly useful golf analogy to explain the core problem: agents are “playing” all day long, on different levels of difficulty, while supervisors are juggling escalations, PTO, reporting, and intraday chaos. In that reality, humans cannot reliably watch enough work to spot true patterns, but AI can, because pattern recognition is exactly what these models do well.

We also get practical about what “signals” can look like, including an omnichannel example where an agent sounds fantastic on the phone but struggles with written communication in email and ticket replies. That’s a hidden coaching gap unless you’re analysing conversations across voice and async work. Along the way, we talk about using AI to highlight strengths so recognition is specific, and how this can help newly promoted managers calibrate quickly between foundational coaching and skill refinement.

If you want coaching that feels fair, evidence-based, and actually improves customer experience, listen now, then subscribe, share this with a fellow support leader, and leave a review with the biggest coaching blind spot you see on your team.

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