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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?

#121
post #55

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…

That's a really hot take

Fraud, schmaud! It's the holidays, for pete's sake!

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

#122
post #112
post #107

Earlier quoted context omitted.

>No one's livelihood should depend on having to read the room like a geisha. Why not? Isn't that most jobs? Seems to me a lot of jobs require you to "read the room" in one way or another. If some work doesn't need that, then a machine should just do it since that's what human excel at.

>Why not? Isn't that most jobs? No. In most jobs, employees know specifically what their employers' requirements are, they have specific tasks and itineraries and boundaries. "Know what I want before I want it" isn't an appropriate expectation to have of any assistant.

I certainly would expect, for example, a senior or staff engineer to have far more autonomy in setting the requirements, specific tasks, and boundaries. Being able to predict the technical needs of the company before they are needed is a big part of those roles.

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

#123
I'm using a throwaway account because this post includes some personal information, but I'm a regular HN reader.

I found that an actual CPA is very helpful to me. She has an accounting degree from a top notch school and years of experience working for a Fortune 500 company. However, she wanted more control over her schedule because of her young children so she worked for me a couple days for a few hours each time. She had other clients as well, but I know very little about them since she doesn't talk about them. She has worked for me for at least ten years. I don't need her every day and she comes and goes on her own schedule.

She picks up and opens my mail, pays bills, does my business bookkeeping, works with my tax accountant at tax time, files paperwork and keeps track of contracts, investments, property taxes, franchise taxes, partnerships, trusts, charities, real estate, etc. I can trust her to handle these sort of things correctly. Now, I can always find any finance related document I'm looking for because of her.

I do trust her completely. She grew up and lives in the area and has a family that has ties to many of my social contacts. Nevertheless, I'm careful about security: I maintain control of all check signing, I'm notified electronically of all non-trivial charges and account transfers, I maintain exclusive control of all of my accounts, I own and control the computers that she uses, and require 2-factor authentication for logins to access business mail addressed to her account (I'm the administrator of the email system). She prepares deposit slips for me, but I'm the one that makes the deposits. I could let her do more, but I do all of the interactions with my financial institutions downloading statements, checking balances, setting up direct deposits and so forth. I just give her piles of pdfs to go through that I have downloaded or scanned.

Having an accountant that takes care of all of my personal and business financial affairs makes my life much easier.

I didn't start out this way; I started out with more traditional personal assistants. These were usually younger people that I trusted enough to babysit my elementary school age daughter, pick up my dry cleaning, and perhaps do some shopping for me. This was helpful, but I wouldn't have trusted them to do the things my accountant does. I've discovered that having a real accountant working for me saves much more time. I've also had a few more problems with "personal assistants" because the relationship is inherently a bit personal. One may have to deal with requests like "It's my boyfriend's birthday next month, do you think I could have a party for 25 people on your boat?"

The cost of a having a personal accountant is higher, but she does a great deal of work that I don't enjoy. Because she does some of the work that my tax accountant would have to do anyway, I end up with somewhat lower tax preparation bills.

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

#124
post #107
post #98

Earlier quoted context omitted.

No, the 'executive' part of 'executive assistant' refers to the assistant typically working for an executive, or performing more advanced executive duties as opposed to an administrative assistant, whose role may be more general across a company. No one's livelihood should depend on having to read the room like a geisha.

>No one's livelihood should depend on having to read the room like a geisha. Why not? Isn't that most jobs? Seems to me a lot of jobs require you to "read the room" in one way or another. If some work doesn't need that, then a machine should just do it since that's what human excel at.

People who expect EAs to read minds are watching too many movies with butlers or pepper pots like secretaries.

Imagine asking your EA why they didn't do something you expected them to do without being explicit about what you want.

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

#125
The Founder and the Force Multiplier is a good read (and quick too) - it's real estate related but has a lot of good tips/guidance on the questions you are asking.

Be very explicit with expectations and be willing to follow through with firm guidance on missed goals. You can get lost in being nice or forgiving missed goals because reason X. Reason X can become a crutch and an outlier becomes the normal.

Trust is a key measure. It sound simple... it's not. Trust is hard. Especially at the CEO level.

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

#126
post #112
post #107

Earlier quoted context omitted.

>No one's livelihood should depend on having to read the room like a geisha. Why not? Isn't that most jobs? Seems to me a lot of jobs require you to "read the room" in one way or another. If some work doesn't need that, then a machine should just do it since that's what human excel at.

>Why not? Isn't that most jobs? No. In most jobs, employees know specifically what their employers' requirements are, they have specific tasks and itineraries and boundaries. "Know what I want before I want it" isn't an appropriate expectation to have of any assistant.

At a certain price point, it certainly is an appropriate expectation.

Even at my job, where all my work is laid out for me in the form of Jira tickets, fulfilling unsaid (or unknown) desires is hugely beneficial for my team, company, and career. Sure, I’m technically paid to solve problems, but really I’m paid for the ability to think creatively and execute autonomously.

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

#127
post #21

I hired one early this year through a "virtual assistant" company in the UK (Virtalent), as I don't need enough help for a full time person to be sensible, and they did a nice job of matchmaking. I had an initial call with one of their folks who spent some time going through with me what I'd want done, and then they set me up with someone pre-screened who I had an intro call with and liked. I'd previously tried Fancy…

CEOs should be experts in delegation otherwise they'll get bogged down in some thing they really shouldn't even be thinking about, let alone doing.

Letting go should be a common response, "How do I systematize this?" should be an almost instant reflex.

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

#128

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…

It wasn't just 1 $470 cake, it was $10k of personal charges for herself over 6 months including a revolving $250 a month gym membership.

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

#129
post #21

I hired one early this year through a "virtual assistant" company in the UK (Virtalent), as I don't need enough help for a full time person to be sensible, and they did a nice job of matchmaking. I had an initial call with one of their folks who spent some time going through with me what I'd want done, and then they set me up with someone pre-screened who I had an intro call with and liked. I'd previously tried Fancy…

> custom menu with a high-end restaurant

Can you please expand on this?

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

#130
post #10

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 th…

For the most part I would agree with you. But at one startup, we hired an EA when she was 18. She won us over with her can-do attitude. A exceptional fast learner and would charm difficult clients and resolve problems without even having to be asked.

To use sports metaphors: you want a PA who runs interference; skates to where the puck will be; dives to block shots at the goal.

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