Start with outcomes, not tasks
The classic mistake is hiring for a task list ("answer emails, book travel") instead of outcomes ("inbox at zero daily, trips booked without my involvement"). Outcomes let a great assistant use judgment; task lists turn them into a very expensive checklist.
Test skills with real work, paid
Interviews tell you who talks well. A short paid trial — triage fifty real emails, plan a real trip, draft a real document — tells you who works well. Score it against a rubric you write in advance: accuracy, communication, turnaround, and initiative.
Red flags worth heeding
Vague answers about tools, no questions about how you work, reluctance to be measured, and — the big one — no system for when they're sick or away. A professional has backups; a gamble doesn't.
Or skip the gamble entirely
Services like Orbitaide exist precisely to absorb this risk: vetted assistants, supervised trial weeks, built-in cover, and a free rematch if the fit isn't right. You get week-one productivity instead of a month of interviews.