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Your calendar says “1:1s,” but your brain hears “context switching.” Charlotte Ward sits down with Reagan Helms, VP of Customer Experience at Planning Center, to unpack a practical way AI can make us better managers: a management assistant that strengthens one-on-ones without turning leadership into autopilot.

We get specific about how Reagan built his system and how it evolved, from separate AI chats per employee to a persistent copilot that can pull the right notes at the right time. We talk about the real-world plumbing behind “AI for managers” including Notion as a human-friendly interface, why Notion can be painful as a retrieval layer, when spreadsheets are the simplest high-performance backbone, and how a vector database can unlock faster search across qualitative coaching history. We also dig into meeting transcription, prompt refinement, and the discipline of verifying outputs so the manager stays responsible for the data and the decisions.

Then we zoom out to the leadership impact: fuller agendas, fewer forgotten commitments, and an “impartial mirror” that helps you sanity-check whether you communicated clearly or whether an annoying behaviour is actually your coaching taking root. We also tackle the trust side head-on, with boundaries and consent so AI support doesn’t drift into surveillance or creep your team out.

If you’re leading customer support, customer experience, or any growing team, hit play, share it with another manager, and subscribe for more. After you listen, leave a review and tell us: what would you want an AI management assistant to handle first?

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