Jenny Dempsey spent years leading support teams at tech startups. before a layoff led to a two-year job hunt. A chance encounter with a junky old table in a friend's basement led to Jenny's furniture-flipping side business, and then her career flipping podcast. Jenny and Mat get into caring intentionally, using AI to help you work out your values, and what to do when a friend is out of work.

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Some key moments

  • (3:27) What DJ requests and feature requests have in common

  • (6:41) "Should I build it just because I can?"

  • (7:47) The Monzo co-founder who records every conversation

  • (12:16) Trust gets built when something goes wrong

  • (21:21) Some people will wrestle with a bot, some just want the answer

  • (23:34) A year spent teaching an AI tool to say "I don't know"

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

  • Understand the job before you AI the job. Don't automate it away until you know the true extent of the work.

  • People are adaptable. Some customers will happily go back and forth with a bot until it gets there, and many are OK with trading off mostly right for very fast.

  • Be responsible. Not just in doing the right thing yourself, but in standing behind automated answers and decisions, and making mistakes right.

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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.