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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?

#41
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 assistant is unavailable.

They specialize in supporting entrepreneurs. They are a small company so every client is valued and given a personal touch.

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

#42
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…

[deleted]

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

#43

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!

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

#44
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…

> 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. good for you, but yikes, man, that made me cringe. you might want to re-think if you'd be comfortable giving the same tasks to a male personal assistant, or if you've somehow unconsciously engineered a large financial/power imbalance, in the disparity between your gross yearly income and wh…

An interesting note is that small business couples, where the man runs the trade-end of things (physician, skilled trades, etc.), and the woman runs the "managerial"-end (billing, paperwork, etc.) seem to be the most stable of couples.

In matters of money, there are less secrets/unexpected swings; and you both have to be invested in the success of the business, ergo one's livelihood and goal-achievement-vehicle (e.g. for vacations, new cars and appliances, better house, etc.).

Plus, if you cannot tolerate one another and cannot work well together, then you'll know soon enough that perhaps the two of you are not compatible in a partnership (and really, that's all a marriage is if you work for a living -- a partnership to help you both reach your goals).

An added bonus, is that it breads closeness, rather than only seeing your significant other for a few hours every night/morning, and the weekends.

Massive financial/power imbalance? Very. Are both people getting what they want from the arrangement? I would imagine so. The ones that weren't have left/had everything crash and burn, or are on their way.

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

#45
post #19
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…

You usually don't have a sentimental relationship with her, that's another difference

[deleted]

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

#46

Earlier quoted context omitted.

> 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. good for you, but yikes, man, that made me cringe. you might want to re-think if you'd be comfortable giving the same tasks to a male personal assistant, or if you've somehow unconsciously engineered a large financial/power imbalance, in the disparity between your gross yearly income and wh…

An interesting note is that small business couples, where the man runs the trade-end of things (physician, skilled trades, etc.), and the woman runs the "managerial"-end (billing, paperwork, etc.) seem to be the most stable of couples. In matters of money, there are less secrets/unexpected swings; and you both have to be invested in the success of the business, ergo one's livelihood and goal-achievement-vehicle (e.g.…

> small business couples

so in my opinion two people in a romantic relationship that also own/run their business together is a completely different thing than what the 'helsinki' poster described, unless their paid assistant they found on craigslist also has other, uhhh.... duties

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

#48

Earlier quoted context omitted.

Ah, I think you just misread, then. They seem to have realized what the arrangement looks like after the fact.

this is why I said "unconsciously", I'm asking them to reflect on whether or not they would have hired an equally-or-better qualified male for the same duties. or whether they went straight to "i'm gonna hire a housewife" without thinking about it as a specific choice. if by some chance the original poster here is not a dude, it's a whole lot less sketchy in my opinion.

Makes sense. Hopefully your comment was beneficial for them.

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

#49

Earlier quoted context omitted.

An interesting note is that small business couples, where the man runs the trade-end of things (physician, skilled trades, etc.), and the woman runs the "managerial"-end (billing, paperwork, etc.) seem to be the most stable of couples. In matters of money, there are less secrets/unexpected swings; and you both have to be invested in the success of the business, ergo one's livelihood and goal-achievement-vehicle (e.g.…

> small business couples so in my opinion two people in a romantic relationship that also own/run their business together is a completely different thing than what the 'helsinki' poster described, unless their paid assistant they found on craigslist also has other, uhhh.... duties

Absolutely. It was mostly a tangent I wanted to write out.

On "other duties," I think a lot of people have that mindset in a partner: mechanically do these things that benefit my emotional state, while I mechanically do my things that benefit their emotional state, and repeat until death.

With the common form of payment being money and material goods, for material services. Transactional.

A disheartening state of affairs, but more common than not.

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

#50

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.
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