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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?

#71

Earlier quoted context omitted.

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

I think most people assume it's okay to for example, use the office printer to print a return slip for a package you're going to mail back on your lunch break. If the volume for your line of work is tens of thousands of pages, maybe printing 470 return slips is just y'know, fine, gets lost in the noise and makes everyone's life easier to just let it happen.

My take is that the difference here that makes this socially acceptable is that there is a large reduction in total cost when the employee uses the office printer. If an employee uses a printer, the cost is the ink and paper. If the employee did it themselves, they would either need to take a special trip to a print shop or invest in a printer themselves. The total cost of the latter is much higher, maybe $5-$10 of the employee's time vs $0.03-$0.05 in ink and paper. We imagine whether the employer would be willing to make this trade (give $0.05 so the employee would gain $5) and assume the employer would, so the "theft" isn't really a theft.

On the other hand, buying a $470 cake with your boss's money is no more efficient than paying yourself. It's "just" stealing.

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

#74
This seems obvious, but you have to be willing to do a bit more work at the beginning before the assistant can help you do less work.

Like, you have to have the time to explain processes to them soup-to-nuts, and then also occasional periods of time for them to check in.

Some people hire assistants or temps because they're overwhelmed and/or there are tasks that they have mental blocks about (as opposed to tasks that they would just like to have taken off their plates). But then their mental blocks are too strong for them to train the person in the task that's triggering them. Or they're too busy to train somebody to help them become less busy. So just make sure to avoid those pitfalls.

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

#75

Earlier quoted context omitted.

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…

Cool website. The site appears to be EA-focused. Do you also have a PA-focused product for things like help scheduling my personal flights, workouts, managing my calendar, doing random research for restaurants, collecting all my tax documents, etc.?

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

#76
post #39

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…

I've had my PA arrange doctor's appointments, it's great. It's not a matter of working too much, it's that I only have so much mental energy to go around. Decisions can be draining. Dealing with people can be draining. These things aren't draining to the same extent for everyone.

These days with everybody understaffed, making a doctor's appointment can be very time-consuming, as well! You might on hold / re-routed and the whole call could take 15 or 20 minutes, which is a lot in the middle of the day.

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

#77
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…

As a counterpoint to the flak you seem to be getting for this comment, I am awful at admin stuff and my partner is better at it and has more free time than I do. since we moved in together, and especially post-pandemic, I have been surprised at how much we have fallen into traditional gender roles - I had never wanted or expected that in a relationship. To the point where I've been considering hiring a PA for exactly those kinds of misc tasks you mention, precisely to prevent my relationship from further developing such '1950s' dynamics. I really don't see what is cringeworthy about that.

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

#79

Earlier quoted context omitted.

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.

Ah, I figured the housewife comment would wreak some havoc, but I can’t really think of a better way to describe. There is no emotional or romantic attachment. If anything, it is friendly, at best. Nothing to really read between the lines on this. It’s a transactional, platonic relationship.

I'm a woman. I've worked in office jobs. I frequently have noticed that getting "life" stuff done is very hard because office jobs were created in the 1950's, when they assumed everyone had a wife at home to take care of "everything else." It makes sense that helsinki is describing his assistant as a 1950's housewife, because all those tasks are the ones that are hard to do now, and where the gaps are these days.

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

#80
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.
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