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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?

#51

Oversight is extremely important for a PA. We had one at one of my old firms charging 10k of personal charges to her boss' cards and then just approving it herself because she did the invoicing and his approvals. If I recall, she billed a $470 custom tiered birthday cake for her boyfriend to the card and also had her Equinox membership on it. EAs are safer ground and less risk but with PAs they can become too entrenc…

And yet expensing $470 for a custom cake for an important client who's birthday party you have to miss because you're heading up the shareholder meeting may be money very well spent. As long as most of the $470's are well spent, and total value for money is better than someone else could achieve, I don't actually mind who's boyfriend gets a fancy cake. But I do need to have confidence that I'm seeing enough of the pi…

WTF? I would absolutely NOT be OK with blatant, unambiguous theft from my PA.

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

#52
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…

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?

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

#53

I want to plug a friend's company that she bootstrapped: https://www.chatterboss.com/ . They offer remote executive assistants on demand. There is no commitment. You pay for the hours they work for you. They care very deeply about the personality match between you and your assistants. On top of that, they strongly believe in documentation and a cover system so you'll always have coverage even if your primary assistan…

This looks great, and I see they have a good reputation on Glassdoor and appear to pay the workers a decent percentage of the fees. Thank you!

Hey!! Thanks for noticing the Glassdoor reviews we work really hard to make sure assistants are happy and focus on highest possible retention:)

I bootstrapped ChatterBoss for past 5 years after being a personal assistant/chief of staff myself.

If you have any questions about working with VA’s happy to answer, whether you go with us or end up somewhere else: https://calendly.com/chatterbossapp/chatterboss-valerie-trap...

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

#54

Earlier quoted context omitted.

Says the person that didn't make their own forks

Arranging a dentist appointment and making your own fork is a very different amount of time commitment.

And yet both can be too much for some people.

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

#55

Oversight is extremely important for a PA. We had one at one of my old firms charging 10k of personal charges to her boss' cards and then just approving it herself because she did the invoicing and his approvals. If I recall, she billed a $470 custom tiered birthday cake for her boyfriend to the card and also had her Equinox membership on it. EAs are safer ground and less risk but with PAs they can become too entrenc…

And yet expensing $470 for a custom cake for an important client who's birthday party you have to miss because you're heading up the shareholder meeting may be money very well spent. As long as most of the $470's are well spent, and total value for money is better than someone else could achieve, I don't actually mind who's boyfriend gets a fancy cake. But I do need to have confidence that I'm seeing enough of the pi…

That's a really hot take

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

#56

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.

random thought on that, at least not unless you're a super wealthy person or very high ranking politician who literally needs the services of a "body man"

https://en.wikipedia.org/wiki/List_of_body_men

https://en.wikipedia.org/wiki/Reggie_Love

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

#57

If you need a personal assistant for your day to day life due to how much you're working, consider the idea that perhaps you're working too much. CEO or not, no one needs to let their work consume their life. It's your job to set an example for the rest of the team. Others might see how much you're working and assume that they need to, too. I've seen it happen a few times. EDIT: Sorry, I failed to mention, my comment…

>If you need a personal assistant for your day to day life due to how much you're working, consider the idea that perhaps you're working too much.

Isn't that exactly the point? That OP did consider that they're working too much and are looking to delegate some of that work to someone else.

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

#58

Earlier quoted context omitted.

And yet expensing $470 for a custom cake for an important client who's birthday party you have to miss because you're heading up the shareholder meeting may be money very well spent. As long as most of the $470's are well spent, and total value for money is better than someone else could achieve, I don't actually mind who's boyfriend gets a fancy cake. But I do need to have confidence that I'm seeing enough of the pi…

WTF? I would absolutely NOT be OK with blatant, unambiguous theft from my PA.

I would probably be ok with a few $470 cakes here and there… if I was in the position to have a PA that is

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

#59

Earlier quoted context omitted.

But it doesn't matter if you like doing your work. If you're working all the time, to the point where you can't arrange a doctor's appointment, you're working way too much. When you're in a leadership position, it's a matter of time until it impacts the rest of the team. The one personal task that takes a lot of time that I'd consider outsourcing would be to go to the store to pick up my prescriptions. But even that…

> If it's a work necessity, they should consider making a personal assistant a company benefit I have seen workplaces with concierge service for employees to handle personal tasks - I'm actually surprised this isn't more popular. Tech companies definitely are known for meals and snacks and coffee being provided, I think that is in the same direction. To your question, scheduling meetings and travel can be a huge time…

It's telling that most of your examples are business related, whereas OP said that personal tasks are first and foremost. But if you actually try to name some personal tasks, it becomes difficult. The sole realistic example seems to be "anything where you have to be on hold on the phone."

I don't think that life admin tasks increase as you get busy. Life stays the same, and work consumes proportionally more.

Would you use an EA to take your kid to school? Pick them up? Your life needs to be on hold for those things, but to me it feels really strange that some people would want to outsource it in the name of work.

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

#60
post #38

Earlier quoted context omitted.

That's interesting. Are you saying that instead of telling her "I want to take next Friday off," she tells you "I cleared your schedule for next Friday so you can take off?"

I wouldn't bother hiring a PA that wasn't proactive to the point of doing that sort of thing

Proactive! More like telepathic
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