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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?

#201

Earlier quoted context omitted.

You're the second person I've heard say this lately. To me, using Calendly feels like demurring to the reality that you have times that work for you, these are the times that work for me, my respect for you is so strong: pick any one of them, and I'll be there. If anything, the posturing seems submissive.

Nope, because if you are a heavy calendar user there are tons of things that could be trivially shuffled. A calendly link is “I will fit you in only if it’s extremely convenient for me”.

“Here’s the link to my calendly. If you don’t see anything that works in the next week or so, just send me over a few times that would work for you & I can reshuffle things to make one of them work.”

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

#202
post #25

After speaking to a friend who lost a lot of money due to a PA that purposely scammed them - make sure they are trustworthy and check their work. They will really be in a good position to cause a lot of harm (even if by accident).

How does one manage this risk? Presumably they need your credit card number pretty immediately, and bank or other sensitive information (SSN) within the first year or so. They would have all the necessary bits to open credit lines at that point. And in the meantime, they could run all sorts of unauthorized charges. Do you review the monthly credit card bills for a couple months, a couple years, or forever? How do cre…

> How does one manage this risk?

I'm not really in a position to advice risk mitigation - I'll ask my friend if they have any retroactive advice. That said, a few words...

> And in the meantime, they could run all sorts of unauthorized charges.

I think this is something that you would speak to your bank about - at least giving them the heads-up regarding this arrangement. It should be possible to get flags set against your account encase of certain activities. I would go as far as not to tell the PA about this arrangement if possible - if they accidentally trigger an alert due to malicious activity then this could be to your advantage.

> Do you review the monthly credit card bills for a couple months, a couple years, or forever?

I would be checking all charges indefinitely, mostly concentrating on the larger substantial charges. I can't imagine such a review posing much of a burden in most cases. You'll likely find that somebody acting maliciously will become more emboldened with time.

> I assume they don't treat them the same as fraud resulting from a stolen card.

That will depend on the arrangement you have setup.

Hope that helps.

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

#203
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…

In this thread there are bunch of well-intentioned but vague answers that don't address the critical "how to find a good EA" part of your question, or answers that do address it via some kind of "virtual EA" service, of which there are many. This turns out to be a super common pattern; very few people really know how to systematically find good EA's.

Just a couple months ago I spent an absolute ton of time doing trial-and-error trying to hire a good EA, ended up wildly successful, and here's what I learned:

There are several methods for finding an EA, sorted below in order of goodness.

Method 0) Find an underemployed person working the front desk at some non-corporate institution, hire them for lucrative side jobs, escalate slowly. Good candidate institutions are poor NGO's, political parties, arts-and-culture related orgs like theaters, and language schools. Obviously this depends on you having access to such an institution, which is hit or miss.

Method 1) Freelancer.com. By far the best assortment of candidates, most enthusiastic replies, least-bad website. You can post a "Project" here searching for an EA with clear examples of likely duties and a brief description of compensation, and get a ton of inbound interest. Freelancer will eventually ban your account for this, because they can't figure out how to monetize this type of transaction, so use burner accounts and try to avoid posting Zoom links or phone numbers, which will trip their crude automated "customers cheating us" detector. Usually you'll get about 24 hours until banning, after your first attempt to contact a candidate off the Freelancer platform. Often they will preemptively assign you a "Freelancer.com employee to help you sift candidates, at no cost to you." This person is just a nanny who will scold you for being an unprofitable customer; they can be safely ignored.

Alternate approach: Hire EA candidates through Freelancer for a small one-off task, then transition to off-platform contact, this reduces bans.

Method 1.5) Fiverr, similar to Freelancer but varies by city/country more.

Method 2) GreatAuPair.com. Decent candidates actually. Dumb slow website, stupid pricing model, bait-and-switch UX. Mostly expensive all around.

Method 3) Country-specific "Find a plumber/find a moving service" type sites. Examples are like maybe fixly.pl or Taskrabbit. Hard to generalize about these due to breadth, but mostly inferior results to the bigger international sites.

Method 3) Websites related to "hire a virtual assistant." Very spotty quality, hit or miss, many foreigners who don't actually speak your language. You really want a real person in your city, ideally in your neighborhood.

Method 4) Gumtree/Craigslist/classified-sites. Low signal-to-noise ratio, don't recommend.

Whichever of these methods you use, you should follow a few very important rules (again sorted in order of importance descending):

Rule 1) Pay efficiency wages. Your EA is a you-amplifier; if she can perform some intervention in your life which saves a marginal hour of your time, you should value that intervention at close to the same price you assign to that marginal hour of your time (which is to say, astronomically, because you are a rich software person whose time is very expensive). This leads to things like "You paid $100 USD for your EA to semibriefly stand in line at the post office."

New EA's will be confused by the giant piles of money you are throwing at them, will wonder if it's a trick or a scam somehow etc. You will end up repeatedly emphasizing that you are not stupid, not throwing away money pointlessly, not dishonest, and in fact are acting rationally. Experienced EA's won't bat an eye and will take your money cheerfully.

Rule 2) Test EA's before making formal hiring commitments. Assign each candidate a (well-paid) trivial test task as an "interview." I use "here are 4 documents in a folder, with no envelopes and no stamps. Mail these 4 documents to 4 different addresses in various countries" as my test task. This is reducible to "find envelopes, find stamps, identify correct international postage, put right document in right envelope, stand in correct line at post office, do this in a reasonable amount of time" and it seems to filter the bad candidates. Obviously one of the documents should be sent to yourself, at your local office address, under some other person's name, so you can evaluate the tidiness/letter sealing/lack-of-coffee-stains etc.

Rule 3) Start by hiring your EA's on a freelance basis, e.g. pay a (task-dependent) bounty per task. Give them one task at a time, pay immediately after task completion via Venmo or whatever the equivalent instant electronic transfer system is in your country, then give them the next task immediately. At the beginning, don't have several open tasks at the same time.

Rule 3.5) At the beginning (and maybe permanently), let the EA control per-task pricing. E.g. instead of you saying "I will pay you $X USD to mail these letters," tell her "Please mail these letters, then let me know how much I owe you for this task, err on the side of charging me more rather than less." There are many good reasons for this structure, especially because you'll never know what delays/slow-moving-lines/problems occurred.

You may have to do a cute little reverse-negotiation wherein you negotiate the price up, often EA's will lowball the prices out of shame/fear/power asymmetry etc.

Have them make a Gsheet to track tasks, completions, and whether or not you paid. After several successful task completions, you can think about hiring them full time on a real contract etc. Very often you discover that you don't need a full time EA.

Rule 4) Avoid virtual EA's, you really want an actual human in your city and ideally in your neighborhood. Most people's lives and business contain a startling amount of boring/delegatable physical-proximity-dependent tasks; when you start looking for these and giving them to your EA, you will be shocked by how many there are.

Rule 5) When your EA quits because she got a better job (and she will, eventually, because anyone reliable/niche enough to be a good EA will eventually be hired by some rich business, often consulting or finance), ask her to hire her replacement by doing the procedure above, as her final task. Give a goodbye bonus as a token of goodwill. She will explain a bunch of context and unwritten procedures to the next candidates, that you weren't even aware of.

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

#204

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…

Oversight of cash expensing is a basic financial control. Nobody, even the CEO, should be approving their own expensing with no oversight. An assistant pretending to be their own boss, so they can approve their own expenses, is fraud and a clear fireable offense.

> Oversight of cash expensing is a basic financial control.

Well, yes. Clearly.

However, point being, that time and time again, for a Personal Assistant who does home/personal life related tasks (not an EA who is work-related duties), the oversight frequently gets overlooked. Lines get blurred and oversight is lacking. Hence by PAs are often prone to fraud.

The CEO of Goldman Sachs had his PA steal over $1.5 million from him before anyone noticed. The Gearbox CEO also has his PA steal $3 million. There are tons of stories like this.

https://www.polygon.com/2018/9/30/17920030/randy-pitchford-d...

https://i1sglobal.com/2021/03/personal-assistant-stole-more-...

https://nypost.com/2018/10/13/how-a-charming-imposter-stole-...

https://www.huffpost.com/entry/identity-theft-personal-assis...

https://www.thejournal.ie/siobhan-maguire-personal-assistant...

https://www.usatoday.com/story/entertainment/celebrities/202...

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

#205

Earlier quoted context omitted.

This response feels strange to me.

You've made two posts negging this idea without providing any actual rationale whatsoever.

Oh, I thought it was obvious I consider it unethical… administrative/HR roles in particular shouldn’t be [potentially] biased by split responsibilities to a specific individual.

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

#206
I used Zirtual to manage myself scaling during the growth of DigitalOcean, we had no EAs till well over 100 people, so I got one for myself using Zirtual. It was a good experience and I'm still using them 6 years later. I think this is a great way to learn what you want without hiring someone.

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

#207

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.

> I'm asking them to reflect Give how absolutely little you know about this situation, that was completely out of line and asinine. You jumped to a conclusion to polish a hobby horse, completely derailed the conversation, and got downvoted for it. I’m asking you to reflect on how condescending and presumptuous your original comment was.

Nah, describing your employee as a 1950s housewife is misogynistic, patriarchal and I'll double down on what I said.

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

#208
post #138

Throughout my 20s (in my 30s now) I worked as a film composer in Hollywood, land of personal assistants. One thing I took to heart was that the best personal assistants weren't looking to use the opportunity get elsewhere. What you want is someone who wants to stay in that role, because as a lot of other comments here point out, it takes a lot of time for the person to learn enough about you to become truly useful ra…

I would love to hear a story of your film composing career. Yes, HN is about hackers and tech and stuff like that, but I think that being generally curious about other things, such as film composing, is only adding to the experience here. Anyway... Just wanted to let you know that you made me really curious :)

Sure. It's actually a little sad, heh, but more on that in a second.

I followed the route that many composers take: working for other composers. First as kind of a general assistant, then doing the boring tasks required to make the process happen, then managing the rigs, then doing production work but not writing, then orchestrating and/or "filling in the gaps" in some cues, then finally writing. I've kind of done it all in terms of tasks/jobs, which I'd imagine most people not involved in that world would even know exist. It really takes a village to get a score done, it's a very interesting world and process.

My profile here is pseudo-anonymous, and given that those whom I worked for are public figures, if you want details it's probably better to chat in private. But long story short I worked on many big Hollywood films, TV shows, and video games. Met and even worked for (and became friends with) some of my heroes. Rubbed shoulders with household name directors and actors. Sounds cool but as most people who have experienced similar things will tell you, it gets normal and mundane fast and you realize that, surprise, people are just people. Most people are nice, some are egotistical shitheads, and often you're surprised which is which. But for the most part, it's just like any industry -- "networking" is bullshit, it's just friends making stuff with friends.

I was very deep in the film scoring community itself and less so in the larger Hollywood system. I was also trending towards games before having to bail out. Long list of reasons why but the biggest one is that I find the creative/technical challenge of writing and implementing an interactive score infinitely interesting.

The best part is that I've recorded an orchestra at every major scoring stage in the world except for Air Studios (really wanted that one). Abbey Road was a particular dream, even though it had to be done remotely, sigh. But man, every time, even after months of not going outside and working yourself to the bone, that moment when the orchestra plays it back is pure magic. I think every composer I know feels the same way. It really makes it worth it.

The hours and deadlines can be absolutely stupid insane, but overall I loved my time in the industry and am very grateful for the experiences.

Anyways. Things were going incredibly, incredibly well. I was set to compose for some games I'm sure HN will be all over once they're out, and so my decades of very hard work were about to pay off. Was in the process of finally getting an agent and putting together a team for myself, rather than working on someone else's team. But then last year I developed an ear condition called Hyperacusis that stopped my career in its tracks. Tried to fight it, tried to work around it, but I slowly came to the realization that the only thing I can do is wait it out, live in silence, hope it gets better, and maybe return to composing if I can. There's nothing else to be done, no treatments.

It's hard to describe just how difficult it is to lose the only career you've wanted since you were 6 years old, that you gave up years of your life to pursue, only to have it taken away at literally the last second before achieving a life-long dream. This condition also prevents me from attending pretty much any loud gathering -- weddings, concerts, etc. I used to love dogs and now I have to avoid them out of fear of their barks. So the impact on my life doesn't just stop at my career. My ears are insanely sensitive to the point that I need hearing protection in order to wash my dishes. It's been this way for a year and is unlikely to improve in any meaningful way (it's improved a bit but not by much, and the "gains" have been in the form of "trading sensitivity for hearing loss"), though I do have hope.

Thankfully, all my years working for other composers resulted in me figuring out that I had a knack for the technical. Etc etc etc I figured I'd like programming. So for now, that's the plan. As a very experienced and opinionated user of music software, I think I could make a very solid technical product designer. I'm actually continuing to work for a few composers, doing things like automating certain workflows where possible, building some custom tools, etc. The goal is to slowly transition to working as a programmer at Steinberg or Ableton or something like that, and then start my own company.

So, going where the road takes me. I certainly didn't expect this but I'm doing my best to make the best of it.

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

#209
post #138

Throughout my 20s (in my 30s now) I worked as a film composer in Hollywood, land of personal assistants. One thing I took to heart was that the best personal assistants weren't looking to use the opportunity get elsewhere. What you want is someone who wants to stay in that role, because as a lot of other comments here point out, it takes a lot of time for the person to learn enough about you to become truly useful ra…

Throughout my 20s (in my 30s now) I worked as a film composer in Hollywood The diverse nature of HN readership never ceases to amaze me. That's really cool.

It's a living :) I replied to someone with more details below if you're interested.

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

#210
post #208

Earlier quoted context omitted.

I would love to hear a story of your film composing career. Yes, HN is about hackers and tech and stuff like that, but I think that being generally curious about other things, such as film composing, is only adding to the experience here. Anyway... Just wanted to let you know that you made me really curious :)

Sure. It's actually a little sad, heh, but more on that in a second. I followed the route that many composers take: working for other composers. First as kind of a general assistant, then doing the boring tasks required to make the process happen, then managing the rigs, then doing production work but not writing, then orchestrating and/or "filling in the gaps" in some cues, then finally writing. I've kind of done it…

> doing things like automating certain workflows where possible, building some custom tools, etc. The goal is to slowly transition to working as a programmer at Steinberg or Ableton or something like that, and then start my own company.

I presume you’ve contacted tantacrul[1] who is now working[2] redesigning Audacity, with a hilarious video on the hellscape of a UI that is Sibelius[3]. I am guessing becoming a UI designer for a major piece of software is less difficult than becoming a composer?

[1] https://www.youtube.com/user/martinthekearykid

[2] https://www.youtube.com/watch?v=RMWNvwLiXIQ

[3] https://youtu.be/dKx1wnXClcI

Thank you for your story - it is a good reminder of the risks we face.

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