You’ve reached that tipping point. Your inbox has become a horror movie. Your to-do list is now a choose-your-own-adventure. You’ve caught yourself saying “I’ll just do it myself” for the 40th time today—and now, here you are, finally ready to hire help.
First of all: congrats. Asking for help is a power move, not a weakness. But if this is your first time bringing on an executive assistant, there are a few things no one tells you (but we will, because we like you).
1. You’re the Bottleneck—Sorry
Let’s rip the Band-Aid off. The biggest delay in getting support? Usually… you.
Hiring someone doesn’t magically make your workload lighter. You need to show them what to take off your plate. That means slowing down long enough to delegate well, give context, and provide access to the right tools. If you don’t, you’ll still be doing it all—plus explaining it over Slack.
The fix? Start documenting recurring tasks now. Trust us, future you (and your assistant) will be thrilled.
2. You Might Feel Awkward at First
You’ve been flying solo for a while. So when someone suddenly asks, “What can I take off your plate?” you might freeze like a deer in executive headlights.
It’s normal. It’s weird to give someone your calendar, your inbox, or your workflows. But building trust takes reps—not just vibes. The more you communicate (clearly and often), the easier it gets.
Hot tip: Start small. Pick low-risk tasks, give feedback, and let your assistant prove they can handle it.