Which Decisions Should You Trust AI to Make?

9 snips

Mar 20, 2026

They debate which decisions are safe to hand to AI, from scheduling and meeting representation to customer support triage. They explore AI making purchases with agent credit cards and setting spend controls. They walk through a domains-of-delegation framework covering sales outreach, internal comms, and hiring workflows. They close by discussing how leadership shifts from deciding to designing rules for autonomous agents.

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ANECDOTE

From No To Full Data Access In Two Years

CJ Gustafson recounts the shift from rejecting AI access to company data to routinely connecting company drives to Claude.
In under two years teams moved from 'never' to daily use of internal data inside AI tools.

ADVICE

Use Agents As Executive Assistants For Meetings

Let agents handle meeting scheduling and basic declines with clear rules, treating them like an executive assistant.
Reserve rescheduling or cancellation of important meetings to humans or require escalation.

ADVICE

Triage Support With AI But Keep Feedback Human

Use AI for first-tier customer support triage and small refunds, but route product complaints to humans for context.
Cap automatic refunds and escalate larger or product-feedback tickets for human review.

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