This guide was produced by Pineapple Operations; Holly Morgan is the primary author, with support from Jennifer Waldmann and Vaidehi Agarwalla (all mistakes are Holly’s own).
1. What is a Personal Assistant? What is an Executive Assistant?
Personal Assistants (PA) tend to be hired remotely on a self-employed basis for ~5-10 hours a week per client. Support is generally focused on saving time in someone’s private life and is primarily administrative.
Executive Assistants (ExA) tend to be full-time, on-site employees. Support is usually focused on saving and managing time in someone’s professional life and is often a mix of administrative, motivational, and generalist.
For simplicity, we’ll refer to both as PAs for the rest of this post.
2. What typical tasks might a PA do?
Admin and research
- Travel logistics
- Research and summarise/book top options for flights and accommodation
- Look into the latest rules around visas, coronavirus, etc.
- Research and summarise/buy top options for a particular product or service
- E.g. laptop, eye mask, credit card, gift, hairdresser, therapist, apartment
- Desk research
- Write/find digestible summaries of specific articles, papers, books, etc.
- Answer questions, e.g. “Are any organisations working on X?”, “What’s the best productivity solution for Y?”
- Household management
- In-person errands, e.g. receive/return packages, process mail, duplicate keys
- Find and manage household workers, e.g. cleaners, childcare, electricians
Motivation and focus
- Regularly run through a tailored list of questions, e.g. “What are your most important tasks this week that you're worried you won't do?”, “Can we think of any motivational hacks now to increase the chance that you'll do them?”, “What steps will you take this month towards becoming your best self?”
- Check that the person has started work, spent 1 hour on top-priority tasks, done 7 hours' work today, etc. or just literally stand behind them like a patient teacher while they write that aversive email
- Proactively address current/anticipated issues with workflows and prioritisation processes based on a deepening familiarity with those systems and the goals behind them
- Disruptive and 'ugh' tasks
- Do tasks that must be done frequently or at a specific time and so would otherwise disrupt the person’s schedule/focus, e.g. regularly check incoming messages for anything sufficiently urgent and important, take notes in meetings, try to get hold of a company that rarely picks up, buy tickets as soon as they go on sale
- Do/start tasks that the person finds particularly aversive, e.g. draft emails, book medical appointments
- Inbox, calendar, and task management
- Provide daily summaries of what today’s priorities seem to be (and stay on top of deadlines)
- Triage incoming emails and politely decline requests as appropriate
- Schedule meetings (with more privacy/professionalism/gatekeeping/nuance than an app)
- Deliver briefings before meetings and conferences
- Manage tasks as they’re thought of, allowing the person to quickly regain focus on their work
- Listen to the person’s problems without judgement :-)
Generalist and miscellaneous
- Drawing on the Assistant’s generalist skill set, ad hoc tasks that there are no dedicated staff for (yet)
- Can involve generally being another pair of eyes (proofreading, being a sounding board, rubber ducking, user testing, etc.) or potentially management in specific areas (social media, recruitment, office, events, etc.)
- This is an opportunity to add a complementary set of skills and attributes to someone’s working life
- So if someone is disorganised, reckless, pessimistic, etc., they could work with an assistant who’s the opposite
3. How much value do PAs add?
80,000 Hours estimates that “a highly talented personal assistant can make someone 10% more productive, or perhaps more” and roughly ranks the related role of operations management 6th on their list of recommended career paths.
4. What makes a good PA?
Some thoughts here, summarised below:
- Support mindset
- Detail-oriented and big-picture-oriented
- Communication skills
- Social skills
- Sometimes: proactive, creative, flexible, okay with some disorder
- Less importantly, prior experience in a PA or similar role (e.g. operations, management/coaching/teaching, research assistance, community-building)
5. How much are PAs paid?
Some data from early 2022 on what EAs were offering can be found here (and it was similar to what EA PAs were asking for):
For the 5 public ads for full-time PAs that we’ve noticed in EA over the past few months that list starting salaries, the average has been £50,600 (lowest: £30k to £47k; highest: £57k or £77k).
The rate offered for part-time PA support has varied between £0 and £77 per hour, with £20-40/h being common. The amount varies according to factors such as: number of hours needed, amount of disposable income (most part-time work seems to be paid out of personal pockets), and skills required beyond those needed for typical Virtual Assistant tasks (e.g. data entry, basic Googling).
But negotiate with each other. And perhaps renegotiate after you’ve spent some time working together.
Factors you may want to consider when deciding on a rate include:
- The PA’s prior experience / ability to add value
- The client’s budget
- How enjoyable / convenient / useful the PA finds the work
- The rate you feel sustainably comfortable with vs. the rate you could do at a push
- Self-employment expenses (self-employment rates tend to be ~1.5-2x higher than those of full-time employees doing similar work to account for insurance and taxes, periods of sickness / holiday / seeking work, office space and equipment, etc.)
6. Is PA work a stepping stone to other work?
Some EAs see PA work as a long-term career path for themselves. But we think that many consider PA work primarily a stepping stone to more senior roles in EA, either with the same individual/organisation or elsewhere. Where this is the case, we strongly encourage PAs to be upfront about this before agreeing to work together and to give their clients an honest estimate of how long they expect to stay in the role.
Onboarding is an investment, so it’s important to think about how long it might take for the working relationship to become net useful to the client. This will vary according to the nature of the tasks, prior delegation/PA experience, how many hours a week the PA works, etc. We have heard the following estimates from the EA community so far:
- From a Research/Personal Assistant: “My guess is that it took me ≈ 4 months to become net useful”
- From someone who has a Research/Personal Assistant: “my assistant became net useful to me very quickly, after a few weeks”
- From someone who hired a full-time PA: in conversation, they gave the estimate of a couple of weeks
- From someone who hired a full-time PA: in conversation, they said that the PA helped them free up time right away
A few more thoughts here.
7. Do EAs or non-EAs make better PAs?
It depends. As mentioned above, we think that many EAs will only be interested in short-/medium-term PA roles (although the idea is that you’ve partially helped to train/trial them for more senior roles with you or someone with similar goals to you, so it’s not a total loss when they leave). But there are other ways in which EAs may prove more helpful.
8. How can I find a good match?
If you’re looking for work as a PA
- Add yourself to the Pineapple Operations talent database. If you’re in or near Berkeley, apply here.
- Check out the 80,000 Hours job board for relevant public vacancies
- If there’s anyone whose work you’d particularly like to support, just approach them and suggest they hire you - there is high demand for PA work in EA in 2022
Finding a good fit
- Consider Akash Wasil’s advice:
- “Be radically honest (don’t present the “best” version of myself– present the most accurate version of myself)
- Meet people (don’t assume that EA is a perfect meritocracy– recognize that many jobs result from networking)
- Be critical (don’t assume that every EA job is highly impactful– take time to compare the expected impact of different roles/orgs).”
- If you have the opportunity to work with several clients, it can be tempting to take on too many. Manage expectations and look after yourself!
If you’re looking to hire a PA
- Reflect on what you’re looking for, and reflect on:
- The kinds of tasks you might like a PA to do
- How many hours a week you expect they will take
- How many of them can be done remotely
- Any particular days/times you’d want a PA to be available and how quickly you’d generally want them to complete a task or get back to you
- How much you’re comfortable paying
- How the role might change over time
- Whether prior EA engagement is important - if not, consider trying a standard VA agency. James Aung (UK), Joan Gass (US), and some anonymous EAs share their experiences here.
- If you’re looking for PAs who have prior engagement with EA, see if there’s anyone promising in the Pineapple Operations talent database and:
- Check references if provided
- Reach out to the PA, telling them a bit about what you’re working on and what you’re looking for
- Arrange a call primarily to establish some initial rapport, but you can also use it to ask interview-type questions and/or to discuss details
- Do a (usually paid) trial to test out your fit for each other, e.g. working together for a couple of weeks or delegating specific tasks
9. What legal set-up should we have?
You may have a bunch of legal questions, such as:
- What is self-employment? Is it the best option? Why? What are the alternatives?
- How do I register as self-employed? / If my PA is self-employed, do I need to do anything beyond paying invoices (via bank transfer / PayPal etc.)?
- Do we need a formal written contract? Do you have a template? What about a non-disclosure agreement? Are there any rules for how an invoice should be written?
Unfortunately, we are not in a position to give legal advice. But we can point you to a few resources and please feel free to ask Holly (LinkedIn, EA Forum) how she’s handled the legal side of things when doing PA work for several EAs.
To find out how to set yourself up as self-employed or to hire a self-employed person - and to check that the arrangement really counts as self-employment - please refer to the official guidance provided by your respective governments. Some resources that may help you in popular EA locations: US, UK, Germany (1, 2, 3, 4), Australia, Canada (1, 2, 3). The Anti Entropy Resource Portal has some general guidance for being an independent contractor (and in Germany), as well as guidance for clients in the US, UK, and Germany.
10. How can we create and sustain a happy, productive working relationship?
These relationships tend to require an unusually high level of communication because:
- There’s more delegating to be done - the work is usually a series of relatively independent tasks rather than broad areas of responsibility with a lot of autonomy
- PAs tend to work remotely, which makes it harder to ask quick questions
- PAs tend to be part-time contractors and therefore miss out on a lot of the background info and support that comes from being embedded in an organisation
Helpful things to discuss at the start:
- Each other’s working styles, e.g.:
- What do you value most at work? What irritates you?
- How can people tell when you’re stressed and support you?
- What things do you struggle with at work?
- How do you like to receive feedback?
- What might people misunderstand about you?
- What are your broad career goals?
- If there is anything the PA should read or be given access to that could provide useful context and help answer their questions (e.g. a Slack workspace to search for relevant info and communicate with the client’s colleagues if needed)
- If there is anything the PA is not prepared to do (e.g. particularly unglamourous work) or would find particularly stressful (e.g. dealing with finances)
- Communication habits going forward:
- Messaging platforms, e.g. Slack by default / WhatsApp if urgent
- Task management tools, e.g. Slack threads, Google Docs, or dedicated apps
- Whether to have regular check-in calls (we’d suggest at least monthly to maintain good rapport and to act as a default space for exchanging feedback)
Continuing to communicate
- You should usually expect a fair amount of figuring things out as you go and being adaptable according to each other’s needs and evolving situations.
- When exchanging feedback, don’t forget:
- Communication, e.g. there’ll be some trial and error to find the balance between over- and under-communicating (and note that more communication is needed early on before you’re familiar with each other’s ways of working)
- Boundaries - performing a service-oriented role in a maximisation-focused community risks burnout, so check that the PA isn’t feeling overwhelmed
- Positive feedback - the PA is relying solely on one person for recognition for their efforts
Tips for clients
- From Peter Wildeford’s notes on the book Managing to Change the World:
- “The best way to ensure delegation goes successfully is to (1) be clear from the start about what you expect, (2) stay engaged enough along the way to make sure you and the employees are on the same page and to ensure the ongoing quality of the work, and (3) hold people accountable for what they deliver. Management problems that appear to be personal issues with a bad employee are much more likely to be about issues with expectations and communication.”
- When delegating, remember to include how soon you’d like the task completed
- For many tasks, a good way to start is simply to do the task in front of your PA, explaining why you’re doing what you’re doing as you go
Tips for PAs
- Some excellent tips on emails/messages that respect your client’s time here (and some good tips here)
- It’s often very helpful to say when/whether you expect to complete a task, give updates if that changes, and say when the task is done (at least keep track of what has and hasn’t been done somewhere your client can access)
- Make the most of your client’s attention while you have it to minimise their context switching, e.g. batch communication where possible and if you notice a message come in when you’re free, reply immediately with your answer or any questions you have
- Be prepared to sometimes have to act on little information if your client is too busy to talk (one Executive Assistant told us “I felt like I had to be psychic with [Vice Presidents]”), but if you feel like they should be communicating more, check in with them about whether they think they’re getting the balance right
- If you’re new to effective altruism culture:
- You may want to skim this intro handbook and look up any jargon
- If you’re familiar with academic, startup, or activist culture, you may notice similarities (e.g. intellectualism, adaptability, and collaboration, respectively)
- The culture is also inevitably influenced by overrepresented demographics
- G Suite and Slack are very popular
- There are very high standards for communication being clear, content-dense, and honest, and people will often communicate their degree of uncertainty about whatever they’re claiming (sometimes marked “epistemic status”)
This guide was produced by Pineapple Operations; Holly Morgan is the primary author, with support from Jennifer Waldmann,Vaidehi Agarwalla and Alexandra Malikova (all mistakes are Holly’s own). Holly would like to thank Ronja Krischke, Jennifer Waldmann, Laura Pomarius, and Alimi Salifou for their work on an early version of Pineapple Operations.