HACKER Q&A
📣 jw1224

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!


  👤 rewgs Accepted Answer ✓
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.


👤 ryan-c
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.


👤 sulam
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.


👤 HalcyonicStorm
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.


👤 Closi
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’).


👤 randycupertino
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.


👤 sshumaker
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.


👤 wly_cdgr
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

👤 paulcole
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.


👤 sirspacey
Check out Squared Away.

Military spouses working remotely.

Great way to make a diff.

Very, very happy with the results.


👤 mmaunder
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.

👤 bArray
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).

👤 nabakin
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


👤 ollerac
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

👤 alistairSH
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.


👤 cbtacy
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.

👤 cmer
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.


👤 anyfactor
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.


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

👤 Arete314159
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.


👤 cm2012
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.

👤 Nevermark
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!


👤 lamperti
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/


👤 ottoid
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.


👤 lyt
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


👤 koliber
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


👤 astraelraen
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.


👤 vzaliva
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.

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

👤 PaywallBuster
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


👤 neom
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.

👤 endymi0n
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.

👤 ranman
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.

👤 throwaway78701
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.


👤 jkahn
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.


👤 HatchedLake721
This is a great resource from Dan Martell https://www.danmartell.com/assistant/

👤 alphabettsy
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.

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

👤 lazyeye
Also try asking on

reddit.com/r/fatfire


👤 8Azw3JFfMiETsm
Post your email here or in your about so you can be contacted.

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

👤 helsinki
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.

👤 newbie789
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.

👤 sillysaurusx
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.