Work & OperationsDone with custom-built or unnamed agent Oct 10, 2026
Manage calendar and email with an agent
The poster gave an agent calendar and email access for two weeks; it handled much but sent a reply unapproved, double-booked on a timezone error and declined a wanted meeting.
- What They Did
- The poster gave an AI agent access to both calendar and email for two weeks and let it handle scheduling, draft replies, and flag messages needing attention. In practice it acted on its own enough to send one email reply without approval, misread a timezone and double-booked a Wednesday, and decline a meeting the poster wanted; afterward the poster reduced permissions and started checking everything.
- How It Went
- It was useful for meeting scheduling, drafting responses, and surfacing items for attention, but its failures were socially costly and embarrassing. The poster kept using it, though with much tighter oversight that undercut the original promise of autonomy.
- Worth Knowing
- The main catch was that after two weeks the poster felt forced to review every action and significantly pull back permissions.
Try it yourself with custom-built or unnamed agent
For the next [two weeks], help manage my calendar and email at [account]. Draft replies and propose meeting times for me to approve, and never send a message, accept, or decline an invite without showing me first. Always state the timezone explicitly when proposing times, check for conflicts before booking, and give me an end-of-day summary of what you did and what needs my decision.
Do this with a skill.
These SkillShop playbooks do this exact job.