The Perfect RIA Hiring an Executive Assistant With Karen Stewart [Episode 334]
Nov 10, 2025
Join Karen Stewart, an Executive Assistant expert and former Belay client success consultant, as she shares her insights on hiring and managing executive assistants. Discover the key traits to look for in an EA, like proactivity and accountability. Karen outlines a rigorous vetting process with a mere 3% hire rate. Learn about effective onboarding strategies, feedback cycles, and maintaining open communication to build trust. Plus, tips on handling turnover and crucial documentation ensure that transitions remain smooth. It's a masterclass in maximizing productivity!
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Booking Failure Turned System Fix
- Matthew recounts an EA booking failure that left him without lodging, which triggered a swift problem-solving call.
- Karen coordinated a three-way call to own the mistake and redesign the system to prevent recurrence.
Front-Load Onboarding And Check-Ins
- Run an introductory kickoff with the EA leading, then conduct frequent check-ins during the first 30 days.
- Expect day 3, 10, 20 check-ins and a day-30 calibration, then quarterly strategy calls.
Hold Weekly Structured Meetings
- Meet at least weekly (preferably Monday and Thursday) and maintain touch points during the week.
- Expect responses within one to two hours under Belay's response standard.