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

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.

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?

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.

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 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?

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.

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.

Imagine asking your EA why they didn't do something you expected them to do without being explicit about what you want.

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.

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.

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.

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.

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.

* 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.

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.

Military spouses working remotely.

Great way to make a diff.

Very, very happy with the results.

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.

https://en.wikipedia.org/wiki/List_of_body_men

https://en.wikipedia.org/wiki/Reggie_Love

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

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

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.

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 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

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.

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.

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.

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.

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.

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.

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.

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.

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.

if by some chance the original poster here is not a dude, it's a whole lot less sketchy in my opinion.

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.

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.

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 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.

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.

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.