Chrissy Chavez is a senior technical support specialist on the Customers Team at Help Scout, working from Oahu, Hawaii. In this episode, she talks with Mat about switching support tools: why the urge to burn it all down and start fresh is so strong, why doing an audit is vital, and how to walk customers through a big tool switch decision without scaring them off.

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Some key moments

  • (5:48) Chrissy watches "Love It or List It" — "You're messy no matter where you live."

  • (7:56) Half the "missing features" people want from their tools are already there. They just didn't know.

  • (9:51) You might not have to switch tools at all.

  • (15:32) Audit your current tool first — saved replies, stale docs, historical data that could cause AI hallucinations.

  • (20:14) The emotional work of change: "Two weeks from now, we won't even remember it was different."

Too long, didn’t watch? Here’s a concise version

  1. Audit first. The real pain of switching is not the new tool, it's all the old cruft you take with you. Clean up first, before you move.

  2. A tool is a vehicle, not a driver. Your team is still the one responsible for delivering good service.

  3. "Cheaper" is a complicated judgment. The total cost of switching tools needs to include the impact on your team's effectiveness, for better and for worse.

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Mathew Patterson
Mathew Patterson

A veteran support leader, Mat spent years teaching better online support at Help Scout before founding More Human Content. Subscribe to The Supportive or find him on LinkedIn.