Ask HN: I’d like to hire a personal/executive assistant – any tips or advice?

This is the most important question to answer honestly:

Are you really ready to stop doing the things you’re hiring this person to do?

If not, that’s fine. It’s your money and your time after all, but you’ll just end up burning through assistant after assistant and wondering why it’s so hard to find good people.

I found my personal assistant on Craigslist. Very happy I found her. I put up a simple posting, ‘computer programmer seeking personal assistant’. Turns out she was tired of being an au pair and decided this would be a better fit. It’s really life changing. I highly recommend it. She pays my bills, responds to emails, cleans up the apartment, walks my dog, manages grocery shopping and occasionally cooks, etc. It’s not that different from what I imagine having a stay-at-home wife was like in the 1950s, except she leaves every evening.

I recorded a thorough guide based on weeks of research about how I hired an English-fluent VA from the Philippines: https://share.getcloudapp.com/8Luog9qo

I’ve had an EA for three years dedicated to me (before that in my career it was always shared). They are definitely a super power, but only if you trust them. They really have to have a lot of context to do things you’d normally be doing. Without that trust you aren’t going to be getting the full potential out of the role.

I’ll give one example. My EA is aware that I have a desire to take some time off through the rest of the year. She knows what planned family vacations are of course and I gave her carte blanche to clear my schedule so I can take a day off here or there through the rest of the year. She knows my preferences in terms of ideal days of the week, which meetings are easy to reschedule vs which aren’t, what projects are especially hot right now, which execs I meet with that are usually flexible, etc. I keep her up to date on my priorities so she can always shift things appropriately. Project Take Time Off wouldn’t really be possible for me to delegate to her if she didn’t have all that context.

Hire someone with experience and professionalism over someone who is more inexperienced but enthusiastic/ambitious.

You need someone who you can absolutely trust to do something and get it done, and someone that won’t complain that something is ‘beneath them’ when you are genuinely in a pinch and need some help (ie you want someone that is skilled enough at communications to talk to clients, good enough at numbers that they can help with invoicing, but that won’t turn their nose up if you ask them to run an errand - and in my experience, people earlier in their careers can find it difficult to span different jobs that they consider different ‘statuses’).