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Ask HN: I’d like to hire a personal/executive assistant – any tips or advice?
247 points by jw1224 12 days ago | hide | past | favorite | 230 comments
I’m a CEO with very limited free time/capacity. I would love to recruit someone to help out with “everything else” — that means personal tasks first and foremost, but involvement with the administrative/day-to-day tasks in my business too.

Whilst I’ve recruited and managed plenty of “traditional” roles in the office, this area is new to me.

Has anyone hired a PA/EA before, who can share any tips or advice?

Thanks!






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 rather than a time suck or a liability. I.e. you want someone who just wants "a job" and doesn't necessarily want to move on from it. If they want to use this job as a rung on the ladder on the way to where they really want to be, they'll be gone before they're super useful.

Meaning: you must pay them quite well, and not work them too terribly hard. Remember that this is someone who works to live. Give them firm boundaries and time off. Make them feel valued; you get out what you put in in this regard.

This should of course go without saying, and for any employee, not just a personal assistant. But it seems to apply extra here.


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.

Talking with IRL can lead to meeting cool people as well;)

This sounds like a trap.

> I.e. you want someone who just wants "a job" and doesn't necessarily want to move on from it.

> Meaning: you must pay them quite well, and not work them too terribly hard. Remember that this is someone who works to live. Give them firm boundaries and time off.

This is counterintuitive but such good advice.


Why do you find it counterintuitive? "Pay them well to encourage them to stick around" seems intuitive to me.

Most people’s gut reaction is probably to hire someone under intern like conditions.

Ie a young candidate whose main motivation is getting something on their resume and therefore will suck up to you and go the extra mile. OP recommends the opposite: someone who doesn’t go the extra mile, but will be stable and reliable for a very long time.


Think about it. People going the extra mile do it because they want to go beyond what they do. They risk burn-out - in which case they can't do their job anymore - or they move on - in which case you lose an employee and have to find another one.

"Intern-like conditions" has an undertone of exploitation to it; nobody should be exploited.


The paying to encourage them to stick around is intuitive, but lots of people take the approach of "I want to hire someone ambitious who wants to progress, and who is willing to work extra hours where required to get the job done because they have a personal drive/desire to succeed"

The advice here is effectively "find someone who doesn't have strong career aspirations and ensure they aren't working outside of working hours".


I think they're saying it's counterintuitive to want someone who isn't driven to try climb some ladder.

Ah, based on my experiences with assistants, that is exactly the problem. You either get someone who is under-qualified and does not fulfill expectations, or someone who is great, but wants to pursue a career.

It is extremely difficult to find a "stable" assistant.


but wants to pursue a career

Being an executive assistant is a career.


Did you still have the same problem when you offered the latter enough money to dissuade them from pursuing something else?

If you want to keep your assistant or employee around, you need to above market salary and flexibility. Then you need to make sure the employee feels properly valued. If you don't get it right the first time, you'll get it right the second. The important thing is to be above market in everything: salary, perks, work environment, etc. Then you can have these kind of aspirations, realistically.

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.


> 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.


I haven't contacted him but I love his work!!

> 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.

Oh my, sorry to hear this. I can only imagine how hard it has been for you.

Best of luck. If you visit Italy, ping me - I'd love to buy you lunch and chat :)


Rough story. Your optimism shows through, and I’m willing to bet you’ll be successful in this transition. I transitioned into this career from the production design side of things (way earlier in my career than you, only worked on a couple films and a handful of plays). Feel free to ping me if you’re looking for advice. I’ve temporarily added my email to my profile.

To be completely honest, optimism is only showing through because I'm hitting the latter end of the grieving process. It's been a very, very tough road coming to terms with this.

Thank you, I'll do that.


That's a helluva break. Godspeed on your path forward.

When you said composer, my first thought was of Haim Saban. Although you sound like you were at two very different technical levels of the industry, I still love the interview he did with the How I Built This podcast though.

If you haven't heard the story: https://www.npr.org/2018/09/21/650524515/power-rangers-haim-... (or the transcript, if audio can't be modulated to a tolerable level)


Huey Lewis's condition comes to mind , a bit different than yours

https://www.google.com/amp/s/www.rollingstone.com/music/musi...


Yup, very similar except in his case he got well enough to work again. I too had a couple of times where my ears just freaked out and went deaf. Pumped me full of steroids to bring the hearing back. It's been pretty hellish but thankfully I have very little hearing loss -- in fact I'd happily trade some sensitivity for hearing loss, as I essentially hear "too well."

That's an interesting story. Thanks for sharing. Good luck in your future endeavors.

Thank you!

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 FancyHands, and that required way too much micromanaging on my part.

paulcole's comment "Are you really ready to stop doing the things you're hiring this person to do?" is a bit on the nose. Learning to let go and delegate is key.

The biggest value I'd say I get is outsourcing decisions that aren't really important but are likely to cause my to spiral into "analysis paralysis". For example, hiring movers - if I tried to do it myself I'd end up spending hours fussing over reviews.

Another major thing is figuring out things I hate doing (phoning people, filling out expense reports, etc) and let my PA handle them.

It's also nice for me that she's British (I'm an American expat living in the UK) and is fairly experienced as an PA/EA and generally knows lots of things that I don't know I don't know. For example, when my partner and I wanted to have a special celebratory meal, she arranged a completely custom menu with a high-end restaurant, which didn't occur to me as something that I could ask for.


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.


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.


> custom menu with a high-end restaurant

Can you please expand on this?


Almost all high end restaurants (think $200-$300 for a meal) will customise their menu for you, just tell them what you want ahead of time.

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 rest of the year. She knows what planned family vacations are of course and I gave her carte blanche to clear my schedule so I can take a day off here or there through the rest of the year. She knows my preferences in terms of ideal days of the week, which meetings are easy to reschedule vs which aren’t, what projects are especially hot right now, which execs I meet with that are usually flexible, etc. I keep her up to date on my priorities so she can always shift things appropriately. Project Take Time Off wouldn’t really be possible for me to delegate to her if she didn’t have all that context.


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

Maybe thats the 'executive' part of 'executive assistant'? They are taking action based on a abstract goal rather than a concrete wish. At least, that is my interpretation!

If you think about it, this feels like the assistant version of a good developer. From a good senior developer I expect initiative. I expect them to have a high level view of the system while still working on the 'in the weeds' stuff. They proactively create a ticket for later to do that refactoring they think is really needed but we don't have time for right now and they ninja it in on Friday afternoon because they were done early with the work on the feature. Did I have to say anything about that? Nope! They just did it and I give them positive feedback about it when I notice it on Monday.

It seems like you want one person to be willing and eager to fill the role several employees, including half of your own. Or a genie.

I get that you want to down vote this, no worries there.

I respectfully disagree with your assessment though. I work with many such individuals and it's exactly how I got where I am today. By being one of those guys that care. I love working with these guys. It's a pleasure to do so. I really love that I'm at a company right now where we have a lot of these kinds of individuals working together.

Yes I have a label of "manager" on my forehead. All that means is that I have to do some stuff most guys would rather not deal with and that's fine. It means I code less. That's fine. I enjoy the mix. They code more and I enjoy seeing them make decisions by themselves, create tasks to make visible what they are doing and why, so that I can defend them against upper management easily. I can shield them and I do so with pleasure.

On the other hand there are developers that I need to basically do the work for. What's the point of doing 80% of the work myself and then transferring over to them to spend 80% of the time for a task to do 20% of the work? At that point I'd rather not have that person on the team and do the work myself.

And to tie this back to the exec assistant topic: if the CEO has to do 80% of the work, what's the point of the executive assistant?


A personal friend is this form of executive assistant. I think that's effectively exactly what they signed up for - a very wealthy couple pays them to do whatever needs to be done. Delegating everything explicitly seems like it would significantly reduce the value of an assistant.

My understanding is once the trust is built in these kind of roles, the assistant is a professional/personal boundary crossing extension of the employer and is prized for their ability to resolve concerns without those concerns having to surface. Agreed that it can be a demanding, temperamental, unpredictable job.


There are a lot of people in this thread who seem outraged because someone is expected to have skills they don't have. I personally know both people who are, and people who have, this type of help.

There are people in this world who are very good at empathizing and very good at organizing, and those people can make a ton of money as what used to be known as being a majordomo.

https://en.m.wikipedia.org/wiki/Majordomo


This is definitely a weird thread in that regard. Maybe people aren't appreciating how many people will do all sorts of things for money? The more outrageous requirements require a more trusting relationship between employer and employee, certainly, and a skilled EA (or majordomo, it seems) is hugely valuable.

My EA-style friend is in a major US city right now supervising the construction of a house - that absolutely wasn't in their employment contract, is not something they have experience in, but it's something their employer wanted. It's hard to get too up in arms when the position is well paid, exciting, and voluntary.


I think the background outrage levels are abnormal, doesn’t take much for someone to be on tilt.

Could also be some folks thinking if you earn enough to afford an assistant than you earn too much.


People that think like that are setting themselves up to be a lifelong loser.

Paying an EA is no different than paying McDonald’s to cook for you. Outsourcing things you can afford to is how we have a productive society.

If someone can make $800k a year pouring their life into their job and delivering tons of value for customers, that’s great. They should do that even if they spend $100k on an EA.

I’d take 50 highly productive people over 50 clock punchers any day. Demonizing them is just tall poppy syndrome.


My friends daughter is only 17 and quite radicalized, detests anyone who can afford a home, car, etc. It’s quite sad.

That’s the bog standard description of senior software engineers at any top tier companies. You get paid a shitload of money because you’re not just parsing requirements in the bare minimum and building the wrong thing. That’s what outsourcing companies are for.

What about that story implies that it is the work of several people?

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.


Imagine asking a software engineer why they shipped code so slow it made a system unusable when “don’t slow the software down 1000x” wasn’t explicitly in the requirements.

This is exactly the same thing. Assistants are there to help people and to know what to do with high level directives.

“I want to take a stay at home vacation next week” should not require explicit instructions to reschedule everything and notify people…


Maybe some people are flexible and just like to have a random day off every once in a while and don't care so much exactly if it's a certain day or not

Why would they do that in this scenario? There is a world of difference between trusting someone to clear your schedule and tell you that you are taking a day off, and silently expecting them to do that on a specific day.

>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.


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.

Most jobs like you described are super low paid. The more agency you're supposed to use in your job to take decisions, generally the higher paid you'll be. It's like you want everyone to be a drone or else they're being exploited.

I’ve been working with this person for three years. It’s not telepathy, it’s shared context and experience.

Well, I want days off when I want days off, and I wouldn't want that.

She doesn’t schedule things on Fridays and if it were required for something important she would communicate it to you.

That’s right. I have the 6th off because that was relatively easy to clear.

I realize this seems bass-ackwards to how you normally do things. The normal way of doing things results in my not taking days off.


EAs on a mission for their boss are a major pain in the behind, they tend to act as though their boss is the most important person in the universe, which inside the company they work for may well be the case, but they tend to project that well outside the company as well. They also tend to consume a disproportionate amount of time in others to save their precious boss a few minutes.

The main function of EAs for people that aren't all that important is to make them feel more important. "I'll have my EA contact your EA to set up a date for a five minute phone call".


I'll have my EA contact your EA to set up a date for a five minute phone call

I’m not even an executive but this is a big time suck with someone outside your organization so you can’t see their calendar. I wish I could outsource this to an EA


Calendly is a much cheaper option. Managing my calendar would be the last thing I delegate to PA.

I find calendly depersonalizing and extremely insulting. I.e. the shift of power when someone says "Hey, let's find a time to chat" and the answer is "Here is my calendly link, good luck". I usually break off the conversation there.

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.”

Exactly. From my experience Calendly works 99% of time, and remaining 1% is where it is better to handle it personally than through PA.

I am slightly confused, why is saving time for both parties considered insulting?

my take from parents post is that he finds "the shift in power" insulting.

while i agree that saving time is a worthwhile goal, i can sympathise with the unhappiness over beeing deferred to an (online) form for stuff that could be tackeld here and now.


This unhappiness seems to me why it's so important Calendly exists: if it's not important enough to merit a visit to an online form, it's sure as heck not important enough to merit interrupting my flow.

If someone says "Hey, let's find a time to chat", would you refer this person to your PA to schedule a call? I hope not, and just like normal people you would look at your calendar and find time slot right away. This is not a use case for Calendly. It is good for asynchronous conversations.

Breaking the conversation at the point, where you are being offered to pick a convenient time looks like a good question for AITA on Reddit.


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.

Decision fatigue is a thing and if you're an executive then there's more important decisions to be made.

The calendar flips don't scale as well as the EA does. The holidays are just an example, there are a million similar things that the EA can do with the same training.

Not to mention some people are just better at that than others. When I’m operating at my full personal capacity, ‘just spend a few minutes’ is the siren’s call. I’m not an executive but I’d pay out of my own pocket if i could find the right person for that job.

Yeah, the proactive part of it could become so much more than "it's been two months since you took a long weekend— I cleared your calendar so you can have next Friday off," it might also be "and here are 2-3 possible options for gifts for your spouse / activities to do with the kids that weekend / options for date night / birthday cards to send to Aunt Flo / etc etc"

I've never had someone be this role for me, but I definitely know I waste a lot of time during the day (both working and non-working) thinking/fretting/researching these kinds of things, and I could imagine it being a real boon to be able to fully set that all aside, knowing it was in good hands. Nothing is a silver bullet on being able to focus on the things we want to focus on, of course, but it would be one more set of excuses to remove.


Exactly. This is one example, but it scales to many.

Sounds like once there is an initial brain dump, the rest of the year you can unload that stress

We’ve been working together for three years. I wouldn’t try and pull this off on day 1 of the relationship, but after three years of working together we talked about it for 15 minutes in our weekly 1:1 and I have a day off next week that I wouldn’t have had otherwise. Win!

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.


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.?

OP here. While the company is focused on helping entrepreneurs with their businesses, setting up their processes, and planning their roadmaps, I've gotten help with such tasks too. I've had doctors appointments scheduled, a gym membership cancelled, research buying gifts etc. I'm also not the strongest writer so I had help drafting letters.

Disclaimer: I am a friend of the founder. I have no financial interest in the company.


Thanks! It’s a really good question because most assistants are really happy to do both personal and business support, but some will have a preference for one or the other. We can definitely provide support on the personal side of things, and in fact have a number of assistants that specialize in personal support. When we do an intake we understand your needs and then do a pairing based on experience required and personality match. Hope that helps!!

Thanks! This looks perfect, and look forward to supporting them.

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 that they can help with invoicing, but that won’t turn their nose up if you ask them to run an errand - and in my experience, people earlier in their careers can find it difficult to span different jobs that they consider different ‘statuses’).


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.


Agreed - with every tip there is an exception to the rule!

I personally find it hard during interviews to seperate people earlier in their career into the "will be amazing" and "will be a trainwreck" buckets - it seems to be a dice roll when they actually start work.

This might just be my interview skills though - and having my fingers burnt on a poor hiring decision on my behalf that fit into this bucket.


The best interview technique I've used (in addition to all the relevant skill/tech part) was "Tell me about a hobby you're into in your free time?" And then ask follow-up questions.

I think it worked because (1) anybody can talk about their favorite hobby, (2) it relaxes people, as they're the expert, and (3) it demonstrates how much of a self-starter / -learner they are.

The best hire I ever made was because the person worked on their motorcycle and explained the mechanic stuff they'd done during the interview.

I was comparing the candidates afterwards in my head, and was hard pressed to imagine someone who worked on engines for fun in their free time, and wouldn't also be able to do this job. Hired that person, and they were amazing!


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 entrenched in personal tasks which tends to breeds resentment and bring on the "fraud triangle" of pressure, opportunity, rationalization.


I did not know there was a “fraud triangle.” Interesting.

It's an accounting term, I think I first heard about it in a white-collar crime book. https://www.brumellgroup.com/news/the-fraud-triangle-theory/

Fidelity bonding can mitigate some of the risk here, if the EA is a W2 FTE.

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 picture to know that money is being well spent overall, even if that doesn't apply to every individual dollar.


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.


BS. Either is stealing and your attempt at rationalization does not make it something else. We just tolerate some things and level of tolerance varies greatly. There are bosses who would nail you to the wall should you take a pen with you and I also know bosses who would tolerate that $500 cake taken by PA.

I don't think it's as black and white, and I don't think the single dimension of "toleration" works to explain the complexity.

Consider napkins at a fast food restaurant. Nobody would say you're "stealing" if you take one napkin and use it to clean your hands after eating. On the other hand, most people would call it "stealing" or at least ethically wrong if you took all the napkins that were available, far more than what you need. In this case, there's more to our ethical intuition than just "stealing" vs "not stealing". Factors include how much you need the napkins, how much you deprive others of the napkins, whether or not the restaurant would be ok with your behavior, whether or not the behavior is a cultural norm, etc.


Don't forget electricity theft by charging personal mobile phone. And time theft by posting to a forum during work.

In case you did not know in some places employers install monitoring software and cameras and you can get your ass nailed just for that - stealing time. They call it different but one still gets fucked.

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

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.

This kind of analysis may make sense with an employee who handles cash like a bartender or a waitress but I'd think twice about applying it to a trusted position like personal assistant.

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...


That's a really hot take

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

I have hired a number of EAs before. Some general suggestions:

* if you are flexible about location, consider areas other than the Bay Area. Top talent here is expensive. A top flight EA might run 125k/year in the bay. * great EAs tend to have long stable tenures. Ideally they have at least a few roles with 4+ years in role. * For the same reason, EAs through temp agencies tend to be weaker. You can find some gems there but it is usually special circumstances - like they took time off for health or the company folded. (Effectively much worse signal to noise ratio) * Good EAs have the core part of the job (time management) completely down pat and often are hungry for additional projects and can talk about them. Another sign is that they have successfully supported multiple execs simultaneously. They have strong opinions about how they work and the tools they use. * when possible, call references. You should get absolutely glowing ones for great EAs. * interview to make sure they are a culture fit too and aligned with your values. I’ve had EAs who were competent but really brusque/rude and that impacts their ability to be successful.

Less a hiring signal but more of how to think about them: A great EA should see around corners for you. Reach out to me in my profile if you’d like more tips about managing them.


This is the most important question to answer honestly:

Are you really ready to stop doing the things you’re hiring this person to do?

If not, that’s fine. It’s your money and your time after all, but you’ll just end up burning through assistant after assistant and wondering why it’s so hard to find good people.


Hire someone from roughly your own socioeconomic class and cultural background who won't be tempted to defraud you and just wants a low stress part time job while they work on some personal creative project that requires a high level of intelligence and expertise but pays little (e.g. literary translation, experimental opera, etc), respect their time boundaries, and you'll have a loyal and capable ally for as long as you need one

Wow, don't tell my boss. (Physicist by day, jazz musician at night). Fortunately, my class and cultural background haven't been a barrier -- I try not to make people feel inferior. It helps to have a job that's vital, but that nobody understands.

>Hire someone from roughly your own socioeconomic class and cultural background who won't be tempted to defraud you and just wants a low stress part time job while they work on some personal creative project

The original argument was that you don't want someone who will be tempted to leave soon, because that then is a waste of the time spent training them.

How about pay someone from a lower socioeconomic class enough that they won't be tempted to defraud you, and don't be a jerk to them.


It is a reality your employees will steal from you at some point, unless you pay them truly astronomical amounts (and even then...) When you have just one, perhaps you will get lucky. With multiple it is a matter of time.

I've spent more than half of my life working, I've never stolen from my employer and I don't recieve "truly astronomical amounts" in pay.

He’s saying that if you pool enough people together, you will get some bad actors. He’s right, although I don’t know if it applies to the EA situation.

A company I worked at, when we got nicer offices that had actual showers, had someone take a dump in the shower within the first month of moving in. I think we were around 1500 employees at the time. It would never occur to me that this would happen, but now I know to expect anything once you get enough people together.


I literally just said "if you have just one, you might get lucky". With that, I was trying to prevent exactly these responses - if you run a company with a reasonable amount of employees and any kind of inventory (or those employees work for you in/around your house, where your stuff is the inventory), some of it will disappear.

Check out Squared Away.

Military spouses working remotely.

Great way to make a diff.

Very, very happy with the results.


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 credit card companies treat charges that were not authorized by the cardholder but were run by someone who was authorized by the cardholder to use the card? I assume they don't treat them the same as fraud resulting from a stolen card.


> 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.


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


Everyone I know who does this is very successful actually. And they have high retention.

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.

I, too, found it weird but ultimately if two people have some sort of personal or professional relationship that they both enjoy, then the flaw isn’t in them, it’s in my ethics. So now I’ve revised my world view.

Go be a working exec for a few years in a medium sized business and then advise other execs on HR, how to hire, and on business ethics.

Go tell someone else what to do before forming an opinion. Or better, don’t do that either.

This response feels strange to me.

I don’t have to be an exec to have an opinion on ethical hiring.

You’re getting a lot of negativity but there’s some truth to what you’re saying. It’s nuanced, though.

First: to all the people saying this happens all the time 1) define your terms carefully because there are obvious ethical boundaries here one should not cross, and 2) the power dynamic often means these situations will not be raised even if the admin feels taken advantage of.

So, there’s a range of activities you could be asking someone to do for you. To ground the conversation in reality let’s put some on the board:

Office admin work:

Stocking the fridge, event coordination, arranging regular lunches for meetings/team etc.

EA work:

Managing your calendar, making sure you personally have something to eat during the work day, taking notes in meetings, managing agendas for routine meetings, scheduling business trips etc.

PA work: stocking the fridge, running errands, making reservations for restaurants, trips, etc.

I think the issue here is that many of these tasks are immediately applicable to all three domains. Also, there is a lot of potential overlap between these domains. This means it is very easy to slip from reasonable requests to unreasonable requests without realizing it.

I’ll give a personal example. My life is complicated and my wife’s schedule is just as busy. For a while my wife had to run an every other week all hands at a particular time that meant I needed to deal with some kid duties that she handles the other 9 days of the two week cycle. Except, as everyone knows, you cannot simply assume an inviolate biweekly recurrence. When my wife’s schedule needed to change, mine did too. For policy reasons neither company allowed remote access to calendars, so neither of us had visibility into the other’s potential conflicts.

Enter my EA, who manages my calendar (among other things). At company A it was considered fine for my wife and my EA to communicate directly about schedule changes so that my business day was reflective of my personal commitments. Then company A got acquired and at company B this was not considered okay.

Two sets of rational, well meaning groups came up with fairly different outcomes. Company B got there with a bright line rule that says something like: your EA is only there to facilitate your corporate life, and there should be zero mixing with your personal life. Company A got to a different place because of a belief that, when the personal life is intersecting corporate life, it may be appropriate for your EA to facilitate. This requires judgment whereas the first rule does not, but in general executives are required to have excellent judgment in many situations, so what’s one more?

That said, company B is much larger and I can practically guarantee that they once had a policy like company A and then it was repeatedly abused to the point that they had to change it.

Sorry for the essay, but I think you have an interesting point here that deserves more than the knee jerk responses you’ve gotten so far.


This has hardly felt like a strong negative response given my own short replies and fairly predictable attitudes but I appreciate you taking the time to reply.

Another reason that I think it’s unethical to mix business/personal responsibilities this way is because it compromises the role for others who reasonably expect the service. An office manager who’s also doing PA work will likely give the latter precedence. In an HR role that creates a more significant conflict of interest.

At best it incentivizes neglect of needs from other stakeholders. At worst it’s a weapon that can be used for any shady kind of conflict resolution, including burying reports of fraud and abuse.


This is absurd.

I don’t think it was.

I haven't been in this position before, but these people have. Maybe these articles could help.

https://www.roberthalf.com/blog/evaluating-job-candidates/ho...

https://www.entrepreneur.com/article/351915


I recorded a thorough guide based on weeks of research about how I hired an English-fluent VA from the Philippines: https://share.getcloudapp.com/8Luog9qo

Do you want an EA or a PA? They aren’t necessarily the same.

An experienced EA isn’t going to be pleased when you ask them to get your dry cleaning or pick up your kids.


I would say first and foremost... decide if you want a PA, or if you want an EA. They are different, require different skillsets, and should be managed differently.

In my experience, aim to hire someone who is really passionate about the role and loves to enable executives. You want someone you can 100% trust, and who really truly cares about you and your wellbeing.

I have interviewed many EAs to assist me, and one obviously had those traits. She was a fantastic hire, specifically because of those traits. Other people we hired at our company for other executives didn't have that passion and were significantly weaker.

I know it sounds fluffy, but if you can find someone like that, you're already halfway there. Look for EAs who participate in EA-related stuff (groups, conferences, etc). These are the folks who are really passionate about the field. I've also never been able to get the same experience/output from a virtual/remote EA.


I sideproject an afforable VA business so take my advice with a grain of salt.

Build a framework or guideline set. Be as descriptive as possible. Have room for errors but don't expect them to come up with creative solutions. Subsitute expectation with pleasant surprise and instrucions with needs.

You want someone to be an extent of yourself but that doesn't mean they are going extend you, unless you are super forgiving of mistakes and you are extra ordinary in your communication.

Always try to document communication if possible. Helps you to control their mistakes and helps them to remind you when you are being forgetful. Balance postive phrasing, directness and empathy.

This advice set seems a bit too exaggerated but in our remote work setting that is fundamental. But for irl there is some leeway.


You get what you pay for. A bargain EA is more of a burden than a blessing.

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.


Advice? I have an unusually fulfilling jigsaw life developing.

1. I am remodeling a huge home for community events and music education, mansion style (not an actual mansion, but that kind of fun feel).

2. Upstairs I have a study and library for my startup where I am CEO and am working with two collegues and local educators.

3. My girlfriend and I realized it made no sense to live in a separate home when there was room for us upstairs too.

So community center, startup and home all coming together in a beautiful building and surrounding gardens, with aesthetic and structural boundaries making divisions between these shared and separate spaces practical.

Assistance I have:

  I have a fantastic community/event manager in place.

  I have a fantastic contractor who repurposes, upgrades, and expands rooms for better uses or greater adaptability as multi-use spaces.
But I don't have (and have never had) a home assistant or an executive assistant and definitely need both ASAP.

Any advice? Get two people to keep the personal and business separate? Or one person who's work is organized around whatever I need?

Whoever it is, whether one or two people, they are going to be constantly crossing boundaries of community, home and business since they all physically, socially and temporally connected.

If any thoughts strike anyone, now would be a good time for me to be considering them!


I have a pa from the Phillipines who is honestly very helpful for rote data entry tasks, which I have a lot of. Not great for anything that doesn't have explicit instructions.

The problem you’re describing is exactly why we started Double a few years ago. We’ll match you with a vetted EA based in the US, we’ll help you learn what and how to delegate, and we’ll even give you the tools to do it effectively, so you can focus on what you’re uniquely qualified to do.

You can check our website to learn more: https://withdouble.com/


Fellow CEO here and runner of about 20 contractors with 3 VAs.

1 EA who has come through a referral who happened to have worked under another CEO is the only one I think will work out. I have had two other EAs but realized they are VAs.

Referrals play a big key for an EA. Not worth it otherwise based on experience with UpWork. I am paying upto $20/hour and will convert them to full-time in a bit.


Disclaimer- Wife works as a consultant for them [0]

I would recommend you consider platforms that do all the hunting, vetting and training for you. This gives you some liability protection as well as saves you the hassle of looking and interviewing multiple people.

The platform I have in mind does all that, and has a pay as you go model, dealing with US based VAs.

The costs are in line with what others recommend, starting at 30$/hour. They only hire VAs who have more than 3 years of experience being an EA/PA so it should fit the bill. Plus you can always change or get more VAs as you need, depending on the skill set required for that task.

From what I know, most of the clients are CEOs who want much of their non essential chores (calendar management, email management, personal shopping etc) taken care of. And once you train one VA, they document it and you don’t have to train new ones anymore.

[0] https://www.hibyron.com


This 2 hour video from David Perell is a phenomenal explanation of all the things you ask about. It talks about hiring, onboarding, and working with a personal assistant.

https://www.youtube.com/watch?v=6ug9fey6GhE


Curious to why this is "unlisted", and in fact it has only a bit more than a thousand views.

Because it’s really popular to hate people with money right now. “How to hire a personal assistant” is a problem only people with money have.

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.


I am also a CEO and while my work EA duties are covered I ocassionaly need some help with personal stuff. I decided it is not enough to hire a proper EA, and for several years now using Magic ( https://app.getmagic.com/s/MkD2hLR ) for occassional tasks like rebooking airplaine tickets, finding last minute appointement slot, etc. I am very happy with the experience.

I don't know any advice, but I know of a good one - https://www.eiskey.co/

Not associated, but I follow the owner on twitter

https://exec-va.com/

They'll match you with a few options. All their candidates from from eastern europe but don't expect a "good deal", they'll still run you for at least 1000-2000 per month.

There's other options or agencies like this, you can search and contact them to show you their options/services


Whoever you go with I'd advise against going with someone who is an existing friend or family member. It creates a hierarchical relationship where there should only be an adjacency.

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.

I'm at the same stage currently, and while I have lots of experience hiring developers, I'm a bit stuck at what to ask a PA/EA and how to evaluate it. Do you go with any test tasks, stuff like that? Happy to hear from your experience.

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.


Fellow CEO here. I've tried a few things over the years and have now had an EA for at least 5 years so I think I've got a good grasp on what works and what doesn't.

Many years ago, I tried a remote VA. I'm on my second in-person EA. I've tried delegating a lot of different stuff - some works, some doesn't.

In no particular order:

* Remote VA. Don't even bother. They're of limited usefulness and it will come down to more work in communication for you in the end. They don't know your local environment, city, employees, customers.

* Personality. You want someone that's competent, smart and capable, but also humble. Would you be proud to have them talk to your best client to reschedule a meeting - would it be a great customer service experience? Do they make people feel welcome and offer them coffee? Is nothing beneath them - they're just as willing to put coffee cups in the dishwasher as well as update a spreadsheet? You want a great, friendly attitude and competence.

* Trust. You have to trust them. This depends on them as well as you: will they do the right thing? They will require time to figure out what your preferences are. It's unfair to expect them to read your mind. You need to coach them on that. But they also need to have an innate sense of what good looks like.

* Some things delegate well and some don't. Especially some personal items. An EA is ace at scheduling a 12 person meeting, venue, lunch, catering, and making sure it suits you. But it's a pain in the ass to get them to update your auto insurance, because they won't have authority on your account and it's such a pain to get it.

* Letting go of the small stuff. Do you care about exactly what kind of wine a client gets as a gift? That's hard to delegate time effectively. Or is it a price range and the EA's choice? Much easier. Similarly with scheduling meetings. You need to give your EA carte blanche on your calendar - within the expectations you agree. I don't do meetings before 9am or after 4pm. But within that, she is fine to schedule what is needed.

* Training yourself. You need to learn to use an EA if you haven't had one before. Surprisingly, this takes a while. It's much harder to delegate control your personal items - including your calendar - than delegating other items. You might think that because you have staff you're already ace at delegation, but this is different. You're actually giving up some personal choices in order to get more time. It was also much harder for me to ask someone to go out and buy X gift for my wife urgently than to delegate other functions. But you get used to it.

Hope that helps. Overall EA's are a massive time saver and make some administrative tasks just disappear. Really valuable for me.


This is a great resource from Dan Martell https://www.danmartell.com/assistant/

There are companies that offer this as well. It’s useful if you don’t need a full-time assistant. The downside is you’re sharing them.

Go through a staffing agency. They will manage background checks and can introduce you to many people across a variety of skill sets.

Background checks only tell you if they've been caught before. It's the first step, but it shouldn't be the only step.

Also try asking on

reddit.com/r/fatfire


Post your email here or in your about so you can be contacted.

I don't have any advice, but I know of a good one - https://www.eiskey.co/

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 that different from what I imagine having a stay-at-home wife was like in the 1950s, except she leaves every evening.

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.

I'm a former homemaker and I've studied women's history to try to figure out how to make my life work.

I think we need to rethink how we configure work. Serious jobs almost always implicitly assume it is designed for a male breadwinner with a full-time homemaker wife.

I think it's refreshing to see some of the comments here acknowledge that.


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?

Housecleaning is a very common stand alone service, and grocery shopping/delivery is fairly easy now too.

Do you really want an individual, or just a service?


Is instacart going to find the exact brand of kombucha you want and be able to substitute it when it's gone? Will they put it in your fridge for you and leave one out on your desk?

An EA/PA is low touch and avoids all the context switching. They're a dependable person you have a working relationship with rather than hit or miss gig for hire.


A service will always be a worse experience. A real human being can mod you and make time for you (this is what you pay them for). To a service, you are a number that the bare minimum is done for to ensure your money comes in.

True, I already have a cleaning service. They come every two weeks and clean the house. Honestly, I'm not satisfied with instacart and all the hidden fees they have/had (last time I used). What is interesting about an individual is they will learn your preferences and have more context in ones preferences as time goes.

It varies based on her schedule. We aim for 25-30 hours per week. There is a lot of downtime on her end, which I am fine with.

What sort of salary are you paying her? Interesting idea but a tough sell on handing someone the keys to my bills and personal life knowing it would be tough to recover if they go rogue.

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

How much does this cost you per month?

> 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 what you pay your assistant to do the duties of a "stay-at-home wife". and exactly what you think her role really is.


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.


> 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.


I think that's called caring for someone.

If it is transactional, it's not caring for someone :)

Okay, agree, I misunderstood your comment.

Aren't most who employ the labor of others for things they could do themselves (e.g., getting coffee at Starbucks) leveraging a "financial/power imbalance"?

Or they are arbitraging a time availability and value imbalance to the voluntary benefit of both.

You are a CEO and have five minutes to prepare for a first remote meeting with a potential client that could result in years of business down the road.

What is the time worth to you, to have someone else get the coffee you like?

The important thing ... is treating the person doing services for you as important too, in pay and respect. Because the five minutes they save you by being reliable are worth a lot.


I'd think anyone hiring a personal assistant would be on the advantageous end of a financial power imbalance. Are you just saying a young man wouldn't be hired to clean a house so it's embarrassing when a woman cleans a house? I think the important thing is to pay cleaners enough and make reasonable requests, not refuse to work with them. (I don't have a cleaner, if it matters.)

I'm saying this person seems to have specifically chosen a person for the duties of what they described as a 1950s housewife, which is rather suspicious in my opinion.

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

Correct.

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.

> 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.

Speaking of speech patterns, the one where someone responds to being schooled in multiple ways with “nah…” is an Internet staple. It’s not convincing, but it must be fun to write? :)

You seem to be under the misconception that I have been "schooled". None of the other opinions expressed in this thread in any way change my opinion that calling someone a 1950s housewife is an insult to an employee's dignity.

Makes sense. Hopefully your comment was beneficial for them.

I haven’t hired one, but I’ve been one for a couple (very) different people. In my experience, the factors that lead to success are clear communication and mutual respect. If you’re expecting a telepath but aren’t willing to spend a little while clearly defining your needs (and crucially, what is a successful response to a prompt and what isn’t) early on, there’s a reduced chance of a successful arrangement.

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 is in response to "personal tasks first and foremost." Having someone arrange meetings is a perfect business use case.


My interpretation was that the person likes doing their work and wants to outsource distractions. For a fixed amount of work / day, it's better to spend as much as possible where you're most effective, imo. I have a cleaner and order takeout not because I'm theoretically too busy to clean and cook, but because I'd rather outsource so I can do other stuff.

Put another way, trade is better for everyone.


> My interpretation was that the person likes doing their work and wants to outsource distractions

This is true. For additional context, I’m also a single man in his late 20s, with the blessing/curse of ADHD.

Whilst I can throw myself into my work (and enjoy it very much), I have little interest/motivation to follow up all the other odds-and-ends in my life.

That might mean something trivial, like keeping the kitchen stocked with healthy food. Or more meaningful tasks — like expenses and invoicing — which are essential, but bore me to death…

As I’m lucky enough to be in a position to do so, if I can get some extra help to sort out everything that’s not my forte, I can focus my energy where it matters: on things I’m good at, and enjoy.


I'm certainly no doctor or authorized to give any diagnosis, but not being interested in running errands like grocery shopping, or tasks like invoicing, is not related to, or a sign of, ADHD. I think most people, including myself, find those tasks boring and tedious and would rather do other things.

OP doesn't imply he has ADHD because of not being interested in errands. Quite the opposite.

Nobody likes boring tasks but some people pathologically avoid them while simultaneously worrying about the fact they haven't done them.

Some people --> tons of normal, non-ADHD people

Yes I identify completely. I spent most of the day today dealing with a bunch of address change stuff and other admin I'd been putting off for months and still have a huge stack of personal admin like that that I shudder and do something else every time I think about. If you can justify the cost, having someone to handle the boring stuff sounds awesome.

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 gives me a chance to reflect. It's really quite hard to imagine that it's a significant loss not having a personal assistant.

What are some tasks that need to be outsourced?

(Another way to phrase it: The rest of their team probably don't have personal assistants. If it's a work necessity, they should consider making a personal assistant a company benefit.)


> 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 suck, especially for a CEO that would have lots of both and rapidly changing plans. Logistics for meetings - "party planning" can be a big job and depending on the size of the company there may not be someone separate to do that.

Personal stuff like changing addresses, filling forms for whatever, waiting to have a mattress delivered (I had a former boss send an EA for this), anything where you have to be on hold on the phone. All this admin stuff only increases as you get busy, and it would be great to have someone to deal with it.

Plus there are always special projects - pulling info together for a presentation or something, looking for a vendor for something. I think I'm talking myself into hiring one...


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.


> It's telling that most of your examples are business related, whereas OP said that personal tasks are first and foremost

Yeah that might be because I have no life and am mainly thinking about business :) I don't think anyone is talking about outsourcing family stuff. I agree that would be something to be concerned about.


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.

Why is it that doctors appointments are something that you need to set aside time to make, personally? Why can't somebody else do that for OP?

I don't personally need an assistant, even though I work at the same company as my CEO (who has a personal assistant as well). Him having one doesn't mean everybody needs one.


They are working too much, so now they’re hiring someone to do some of that work, such that their overall work burden is reduced and more focused on the tasks they prefer to work on.

>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.


You're right, I phrased that poorly. I added an edit to clarify. My mistake.

What got to me was the idea that people want a personal assistant to run their lives, rather than their business. That seemed like a red flag, but it sounds like a lot of people disagree.


Because you consider some things to be part of your “personal life” that many people don’t want to be part of their life at all.

I love butter but I don’t want to churn it. So I just buy it from the store. Is that paying the store to run my life?


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.

Exactly this!



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