The Executive Assistant Operating System

Ethan Drower
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The feeling of drowning is not news to anyone who’s been running an internet based business.

We hire cheaper people overseas, teach how them how ot do the things we need in our business, and (hopefully) make some kind of profit on their efforts. A

For being a community that prides themselves on efficiency, I’ve always found it interesting how averse so many entrepreneurs are to hiring their own assistants. Our business runs like a swiss watch, but we forget to file our taxes on time year after year or send thoughtful gifts to our parents (even though we love and appreciate them). If you think about it briefly, this phenomenon makes sense. There are only so many hours in day, right?

If you’re hyper focused on making a company work, dealing with customers, putting out fires, and then of course building the actual product/service… you barely have time to breath, let alone organize your own life.

At least that’s certainly how I felt. Barely staying afloat until the weekend, and then using that precious time with no meetings/calls to catch up on as much administrative paperwork as possible.

“Why don’t you just hire someone to do that for you?”

Ugh. Fuck you.

This is what an average bystander, or mediocre business coach will say nonchalantly whenever an entrepreneru is in the thick of it and really hurting for time and sanity. And it’s the easiest thing in the world to say (which is why it’s so frustrating). It’s the equivalent of telling a drowning person “well if you just tread water more efficiently, you’ll be fine!”.

It’s true, but it’s not always the most useful advice in the real world. But bad coaches and our friends don’t live in the real world of entrepreneurship. They live in the world of idealism, a far easier (and more profitable in the short run) place to be.

So we know we’re drowning, but we don’t have time to build our life raft (or yes, hire someone to build it for us).

The reason for this is that hiring a legit assistant is hard. Training them on how to manage your life (while you can barely keep it together) is even harder. Here are the giant time-consuming, soul sucking tasks one must do in order to start actually seeing results from an assistant.

  • You have to draft a job post that is interesting and enticing to an assistant
  • You have to post it somewhere, and plow through a mountain of resumes of people that didn’t even read said job description.
  • You have to ‘interview’ several people and see if they’re a good fit.
  • You have to figure out if the good fit lied about all of their skills/experience on their resume.
  • You have to negotiate an offer, get them onboard, and train them on your life.
  • You have to evaluate their progress, and course-correct as they make mistakes and learn.
  • Replace them if they leave (without spending another massive chunk of hours repeating this process)

And of course, if your candidate fails in any one of the steps, you pretty much are starting over from scratch with someone new. Now does it make sense why “just hire someone” is absolute nonsense?

But imagine being able to have someone come start working for you today. They’d be able to look through all your emails, calendar, and figure out how you want things to work and what would be ideal for you.

They’d catch onto the fact that every 6 weeks you go get your hair cut, and that you had bookmarked a bunch of flights and airbnbs for that friends trip to Mexico.. but had forgotten to respond to the group email thread and get it pushed through. Then they sat on the phone with your internet company to troubleshoot some annoying billing issues and get you a partial refund credited to your account.

What if you had someone that just drove all of the little things in your life that pile up home towards completion? And then wrapped them up with a nice bow in a weekly summary email. Checked that off, that too, and don’t forget your Mother’s in town so I booked a table at a new restaurant for you both. The info is in your calendar already.

Fortunately for you, you’ve stumbled onto the blog of a meticulous psychopath that finds it enjoyable to build, write and organize insanely detailed instructions on how to do various things… like finding, hiring, and training an executive assistant.

I spent just under a year obsessed with the idea of efficiently finding, hiring, training, and managing an assistant that would run my life without me constantly needing to teach them stuff.

And it wasn’t just about finding that “perfect” assistant, it was about writing instructions so clear, that even if the first person I hired left I’d be able to slot in another and pick up right where they left off. Turnover is killer for a business, and even moreso in a business of 1 (you).

The Components of Executive Assistant Perfection

There are three big pieces to nail when it comes to your EA. Finding them, telling them what to do, and then making sure they do it. Sounds pretty simple, right?

A note on Executive Assitants Vs. Virtual Assistants

This is kind of a funny distinction, but it’s worth addressing here. The main different between an EA and VA (aside from one sounding cooler and more professional) is the autonomy and responsibility to oversee other people. VAs job is to follow the script, over and over again. an EA can be tasks with a broader challenged like “Plan my vacation”.

Like most things, it’s simple but not easy to do in the real world when you’ve got endless meetings and interruptions, and weekends to plan with spouse, family vacation coming up and then the dog gets sick. Life is too messy to start new projects right now (and spoiler alert: it always will be).

So I’ve fast-tracked all three of these big pieces for you in the most plug-n-play way possible. Here’s how it’ll work.

Finding and Hiring Your Executive Assistant

First we need to find the person that’ll take over your life and your daily tasks. This is where things go completely off the rails for most people. They dont’ know where to look, what questions to ask, how to recruit.

There are ton of good remote work job boards these days. To list a few:

  • Upwork (old school, but i still find so many of my best people here)
  • DynamiteJobs -
  • Remoteok job board
  • Infinite more on google


Then we need to craft a job post that will attract the ‘right’ kind of person. I’ve got a template for this, that you customize based on your personality and own values.


Then it’s time to filter out all of the templated or ChatGPT written cover letters from the spam candidates (this is 95% of them). After that, we can actually review and assess the legitimate candidates.

The Challenge

Now that we’ve gotten a few solid looking prospects, it’s time to send them a challenge to do for the next step. Do not bother getting them on the phone at this point, just send the custom challenge (I have the template for this as well) and see who completes it well.

This does a few things, it tests for competency, their level of english (important), and most importantly their level of ‘give a shit’. Are they hungry and competent? We’ll see based on their challenge response.

The Interview

Here’s something a lot of people don’t understand when hiring. By the time you get on the phone with the person, you should already be 90% certain they have the skills you need. The phone interview is for assessing their vibe, and how sharp they are ‘in person’.

Personality fit is hugely important, especially with someone you plan to share a lot of details of your life (and ultimately trust with a lot of personal knowledge about you).

This one is a bit more of a ‘gut feeling’ type of analysis, but you should use the interview questions script I wrote as a starting point, then customize it to your specific needs. Maybe even throw a few technical questions to flesh out the phonies.

The ‘VA Finder Business Models’

I’m not sold on these yet. The pitch is very compelling (they find, train, and vette assistants for you so you’re just ready to rock). The only problem wit hthis, is that they do it at a markup to make money… and that extra pricing could destroy the whole advantage of having your assistant anyways.

Depending on how muc you make at your busines or job, a $25/hour fancy EA might be completely out of the question. If it’s not, then maybe htese services are worth a shot, but i think with a little leg work up-front you can save thousands a year.

Instructions - Telling Your EA What to Do

Now that you’ve spent 2 weeks and hired the perfect seeming assistant. It’s time to put them to work and get them helping you.

If you’ve never hired anyone before, you’re in for a bit of a rude awakening. Even for good employees, you tend to spend the first few weeks (longer on more complex jobs) spending more time teaching them how to do the thing than it would have taken to just keep doing your self.

This is the ‘dip’ in hiring people, where productivity actually decreases (because you stop doing it yourself, and start teaching someone new). This period totally sucks, and can be a real morale crusher, especially if 3 weeks in you find out your new employee is actually terrible.

So the name of the game is to reduce this period as much as humanly possible. We want your new assistant to hit the ground running, and start saving you time from day one. Not day 90.

In my Executive Assistant Operating System, I give you a mountain of ready-built instruction manuals on the highest value tasks for most people (managing your inbox, your calendar, booking your travel etc.) that your EA can start using right away to save you time.

Obviously, I cant pre-write instructions for every task in your life (so many different entrepreneurs need different things), but I can and have given you the framework and templates for building your own stuff quickly. Any afternoon inside Notion with a Loom Video Recorder account is all you’ll need to build up a rich library of explanations of how you do stuff.

Managing - Make Sure Your EA Is Actually Doing the Job

Most people are naturally terrible managers. Even most professional ‘managers’ are terrible at it (as you probably have seen if you’ve ever had a job in any industry).

But you’re not going to be one of them.

Management is hard to set up, but easy to maintain once things are rolling. You do the planning upfront, and then look like a hero later on when the results come in.

There are two big components to this. The first is making sure that your EA is working on the things you want them to (are they spending the time on the priorities etc.). The second is measuring how effective they are at doing things (are the results coming in?).

The temptation is to either go way too casual with both of these things, or way too intense. Too casual and you’re getting a shitty email every weeks about ‘how things are going’, and too intense your poor EA is spending 25% of their time just trying to make your reports about how they’re spending their time.

I’ve experimented with both sides of the spectrum, and I think I’ve found the perfect balance for most small-scale entrepreneurs or solo operators. Included, are my daily and weekly reporting templates (with instructions for your EA on how to fill them out and where to store them), as well as examples of how to set measurable ‘goals and metrics’ for your EA to be measured against.

This is how we know that they’re doing a good job. Your free time is increasing, your website traffic is going up, etc. These metrics will be super specific to your business and life… but usually they fall into the same broad categories.

Let’s Get On With It - Where to Start

Now you should be familiar with the biggest components of managing an EA and getting them rocking for your team from day 1. Where to from here?

You could try to build out all of the pieces we discussed yourself. It took me almost a year of testing and refining (and hiring the wrong people), but maybe you’d be better at it.

Or you could just download the massive and detailed Operating System from me and import directly into Notion. Save yourself months, with a few bucks and 30 seconds of time.

What’s Included in the Executive Assistant Operating System?

The Hiring:

  • Job description templates (attract the right kind of people, not just the most qualified on paper)
  • My list of the most effective and least spammy Remote Job Boards
  • Framework for how to filter out the junk resumes and template cover letters to find the golden candidates.
  • Interview Challenge Template - squeeze out the exaggerators and the talkers, and end up with a list of candidates that actually know what the heck they’re doing.
  • Phone call script and interview questions (find the right fit for you, not just someone that can do the job).
  • Negotation Mini-Master Class. We aren’t negotiating hostages with terrorists here, but you need some skills and info on how what to offer, and how to negotate with your new hires.

The Instructions

  • EA Instructions Galore, including primary life ones like managing Emails, Calendar, Booking your travel etc.
  • Clear and concise templates for you to easily build instructions for common tasks in your own life.
  • A time logging ‘Assessment’ template you can use to have your EA produce detailed analysis of the time you’re spending on every part of your life.
  • Reporting and Goal Rubrics, for your EA to fill out daily and weekly and keep them on track.
  • Prioritization And Goal Setting Tables for you ( plus my personal examples)
  • Social Media Management and Growth Reporting templates (have your EA take over your personal social media posting, and business posting while tracking growth meticulously).

The Managing

  • Your personal productivity/goals tracker (simple to follow, use, and update unlike most over-the-top goal setting systems)
  • Reporting for your EA and progress tracking.

That’s a lot of stuff - how much does it cost?

$8 bucks, seriously.

Why so cheap? Why give away a year of my life’s experience and frankly a shit ton of hours cranking away on the laptop after too much coffee? A few reasons:

Because this isn’t my main gig. I make my cash through my business, i just like this writing stuff and even more so I like sharing it and helping people out.

Also, I want to over-deliver so you’ll leave me a killer review or testimonial video. Maybe with enough raving fans, I’ll be able to sell some more useful stuff down the line.

Try it Risk Free

Look, this things only 8 dollars. If you’re hiring an EA for likely between 10-20 per hour, i’d hope that this price point isn’t exactly an issue.

But if you really think my Operating System is a pile of rubbish soaked in diesel and sweltering in the summer heat, just email me and I’ll send you the money back, no biggie.

Buy this

Try it risk free -

Look, this things only 8 dollars. If you’re hiring an EA for likely between 10-20 per hour, i’d hope that this price point isn’t exactly an issue.

But if you ************really************ think my Operating System is a pile of rubbish soaked in diesel and sweltering in the summer heat, just email me and I’ll send you the money back, no biggie.

Last updated Jul 11, 2023

Complete Hiring Process and Copy-Paste Templates - All my Daily Instructions for Simplifying your life (done by your EA) -- Complete Reporting and Goal Setting Framework


The Executive Assistant Operating System

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