Ask HN: I’d like to hire a personal/executive assistant – any tips or advice?
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!
243 comments
[ 3.6 ms ] story [ 253 ms ] threadAre 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.
https://www.roberthalf.com/blog/evaluating-job-candidates/ho...
https://www.entrepreneur.com/article/351915
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.
if by some chance the original poster here is not a dude, it's a whole lot less sketchy in my opinion.
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.
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.
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
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.
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.
Do you really want an individual, or just a service?
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.
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.
Military spouses working remotely.
Great way to make a diff.
Very, very happy with the results.
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.
Put another way, trade is better for everyone.
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.)
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.
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...
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.
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.
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.
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.
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.
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?
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.
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.
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.
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.
Imagine asking your EA why they didn't do something you expected them to do without being explicit about what you want.
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…
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 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
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.
Could also be some folks thinking if you earn enough to afford an assistant than you earn too much.
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.
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?
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.
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.
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’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
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.
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.
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’).
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.
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.
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!
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.
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.
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.
On the other hand, buying a $470 cake with your boss's money is no more efficient than paying yourself. It's "just" stealing.
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.
An assistant pretending to be their own boss, so they can approve their own expenses, is fraud and a clear fireable offense.
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...
https://en.wikipedia.org/wiki/List_of_body_men
https://en.wikipedia.org/wiki/Reggie_Love
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.
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.
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.
Letting go should be a common response, "How do I systematize this?" should be an almost instant reflex.
Can you please expand on this?
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 do...
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.
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.
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.
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...
Disclaimer: I am a friend of the founder. I have no financial interest in the company.
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 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
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.
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.