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

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

#81

Consider an office manager instead. It better describes the requirements that extend into your organization, and it’s one of the best early hires a growing org can make. If they shine, consider letting them take on HR tasks if you don’t already have an internal HR resource.

Please don’t hire people for business roles where part of their responsibilities are to you individually.

Everyone I know who does this is very successful actually. And they have high retention.

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

#82
post #4

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…

How much does this cost you per month?

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

#83
post #68

Earlier quoted context omitted.

This is really interesting. I wish if I can hire someone to clean my house and do grocery shopping for me. If you don't mind me asking, how many hours/per week she works for you?

Housecleaning is a very common stand alone service, and grocery shopping/delivery is fairly easy now too. Do you really want an individual, or just a service?

Is instacart going to find the exact brand of kombucha you want and be able to substitute it when it's gone? Will they put it in your fridge for you and leave one out on your desk?

An EA/PA is low touch and avoids all the context switching. They're a dependable person you have a working relationship with rather than hit or miss gig for hire.

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

#84
In my experience, aim to hire someone who is really passionate about the role and loves to enable executives. You want someone you can 100% trust, and who really truly cares about you and your wellbeing.

I have interviewed many EAs to assist me, and one obviously had those traits. She was a fantastic hire, specifically because of those traits. Other people we hired at our company for other executives didn't have that passion and were significantly weaker.

I know it sounds fluffy, but if you can find someone like that, you're already halfway there. Look for EAs who participate in EA-related stuff (groups, conferences, etc). These are the folks who are really passionate about the field. I've also never been able to get the same experience/output from a virtual/remote EA.

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

#85
post #4

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…

I'm a former homemaker and I've studied women's history to try to figure out how to make my life work.

I think we need to rethink how we configure work. Serious jobs almost always implicitly assume it is designed for a male breadwinner with a full-time homemaker wife.

I think it's refreshing to see some of the comments here acknowledge that.

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

#86
Fellow CEO here. I've tried a few things over the years and have now had an EA for at least 5 years so I think I've got a good grasp on what works and what doesn't.

Many years ago, I tried a remote VA. I'm on my second in-person EA. I've tried delegating a lot of different stuff - some works, some doesn't.

In no particular order:

* Remote VA. Don't even bother. They're of limited usefulness and it will come down to more work in communication for you in the end. They don't know your local environment, city, employees, customers.

* Personality. You want someone that's competent, smart and capable, but also humble. Would you be proud to have them talk to your best client to reschedule a meeting - would it be a great customer service experience? Do they make people feel welcome and offer them coffee? Is nothing beneath them - they're just as willing to put coffee cups in the dishwasher as well as update a spreadsheet? You want a great, friendly attitude and competence.

* Trust. You have to trust them. This depends on them as well as you: will they do the right thing? They will require time to figure out what your preferences are. It's unfair to expect them to read your mind. You need to coach them on that. But they also need to have an innate sense of what good looks like.

* Some things delegate well and some don't. Especially some personal items. An EA is ace at scheduling a 12 person meeting, venue, lunch, catering, and making sure it suits you. But it's a pain in the ass to get them to update your auto insurance, because they won't have authority on your account and it's such a pain to get it.

* Letting go of the small stuff. Do you care about exactly what kind of wine a client gets as a gift? That's hard to delegate time effectively. Or is it a price range and the EA's choice? Much easier. Similarly with scheduling meetings. You need to give your EA carte blanche on your calendar - within the expectations you agree. I don't do meetings before 9am or after 4pm. But within that, she is fine to schedule what is needed.

* Training yourself. You need to learn to use an EA if you haven't had one before. Surprisingly, this takes a while. It's much harder to delegate control your personal items - including your calendar - than delegating other items. You might think that because you have staff you're already ace at delegation, but this is different. You're actually giving up some personal choices in order to get more time. It was also much harder for me to ask someone to go out and buy X gift for my wife urgently than to delegate other functions. But you get used to it.

Hope that helps. Overall EA's are a massive time saver and make some administrative tasks just disappear. Really valuable for me.

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

#87
post #8

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 re…

If it takes great effort to bestow this institutional knowledge on the EA, is it buying you that much of your time back? You already know the algorithm for when free time can be most easily made. Just a matter of flipping through the calendar for a brief, few moments, versus the hours spent with the EA getting them up to speed on these nuances.

Sounds like once there is an initial brain dump, the rest of the year you can unload that stress

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

#88
post #8

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 re…

If it takes great effort to bestow this institutional knowledge on the EA, is it buying you that much of your time back? You already know the algorithm for when free time can be most easily made. Just a matter of flipping through the calendar for a brief, few moments, versus the hours spent with the EA getting them up to speed on these nuances.

The calendar flips don't scale as well as the EA does. The holidays are just an example, there are a million similar things that the EA can do with the same training.

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

#89
Hire someone from roughly your own socioeconomic class and cultural background who won't be tempted to defraud you and just wants a low stress part time job while they work on some personal creative project that requires a high level of intelligence and expertise but pays little (e.g. literary translation, experimental opera, etc), respect their time boundaries, and you'll have a loyal and capable ally for as long as you need one

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

#90
Fellow CEO here and runner of about 20 contractors with 3 VAs.

1 EA who has come through a referral who happened to have worked under another CEO is the only one I think will work out. I have had two other EAs but realized they are VAs.

Referrals play a big key for an EA. Not worth it otherwise based on experience with UpWork. I am paying upto $20/hour and will convert them to full-time in a bit.

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