Tips & Observations.
Practical notes from twenty years of operational work — the patterns that keep showing up, and the moves that actually help.
Know which layer you're actually hiring for.
An EA handles the day — inbox, calendar, logistics — immediately. A Chief of Staff carries strategy — stakeholder navigation, priorities, organizational design. Hiring EA-level support and expecting CoS-level judgment sets the relationship up to disappoint.
Give real access, not filtered access.
The instinct to protect your inbox is understandable. It also makes your EA 60% less effective. They need to see the full picture to triage it correctly. Limited access doesn't protect you — it just moves the bottleneck.
Brief the relationship, not just the tasks.
Your EA needs to know your decision-making style, your communication preferences, what you'll tolerate and what you won't. That context compounds every month it's in place.
Let them own the system, not just work the tickets.
The best fractional EA relationships produce infrastructure — templates, triage logic, filing architecture — that outlasts any individual task. If you're just assigning work, you're hiring a task-taker. If you're building a system together, you're hiring a partner.
Establish a daily rhythm early.
A brief end-of-day note, a shared task system, a standing 15-minute sync — whatever the format, a consistent operating rhythm turns fractional support into a real working relationship rather than a series of one-off transactions.
These are the things I notice in every engagement. If any of them sound familiar, let's talk.
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