Adopt a daily or twice-weekly update format: completed, planned, blockers, and questions. Keep messages scannable with bullets and links. This creates visibility without calendar bloat, gives you time to think before responding, and enables your assistant to course-correct swiftly, even when your day is tangled with calls, travel, or deep work that cannot be interrupted.
Structure feedback around observed behavior, impact, and next step. Pair praise with specific examples so strengths become repeatable. When correcting, show a better version and explain the rationale. This builds judgment, protects morale, and transforms mistakes into learning moments that permanently upgrade your operating system rather than merely patching symptoms temporarily until they inevitably reappear.
Define response times for urgent, important, and routine requests. Create clear escalation channels—chat, email, or ticket—so issues never stall. When your assistant knows exactly how and when to raise a flag, small problems stay small. You sleep easier, quality holds steady, and work keeps flowing even during holidays, travel, or unavoidable bouts of unexpected downtime.
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