Hire, onboard, and work with an EA

Part 1: Scope

Before you hire, onboard, or develop a relationship with your EA, you’ll first need to properly define scope.  This should go for any role you hire for, but it is especially critical with your EA so that both of you can define healthy boundaries of what their responsibilities are and what isn’t.

Start by conducting an Energy Audit.

I won’t go in too much detail of how to conduct an Energy Audit, because Matt Mochary already does a great job explaining how to do one here.  In a nutshell, though:

Decide which things are draining your energy.

This probably includes things like phone calls, scheduling meetings, uploading receipts, and other administrative tasks.

Create a list of these things, and make a note that your EA will be the DRI for these tasks (with you as the back-up.)

Next, create a list of things that don’t necessarily drain your energy, but you want your EA to be the backup DRI for.

You might still want to own putting together investor memos, or maybe you actually enjoy doing your own scheduling.

However, if push comes to shove and you need to step away for a period of time, your EA should be ready to step in and take over as your backup.  Make a note that your EA will be the backup DRI for these tasks.

Now that you’ve conducted your Energy Audit, congratulations — you now have a scoped-out list of responsibilities for your EA.

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Part 2:  Agency or not?

Part 2A:  Working with an agency

In my time working in Operations at startups, I’ve personally worked with and onboarded over ten EAs, and have interacted with many more.  Many of them came from an agency.

Take the list of responsibilities you made in the previous step and send it to the agency of your choice (or send it to all three, and go from there.)  Depending on how many tasks there are on this list, decide if you’ll need someone who is full-time or part-time.

Regarding budget, you get what you pay for.  The best EAs I worked with were often double the cost of cheaper agencies, but they overall seemed happier, were well-spoken, and worth the investment.

Eventually, if you plan on bringing your EA onto your team full-time, be ready to pay a placement agency fee in the tens of thousands of USD.  This might seem daunting, but keep in mind the ROI here:

1. You know that your EA (like the rest of your team) at this point has full knowledge of your startup.
2. They know how to work with you and your team.
3. There is the peace of mind that the agency won’t take your EA away tomorrow and replace them with someone brand new — something that, technically, could happen if you continued contracting through an agency.

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Part 2B:  Hiring independently without an agency

Although I think this is more rare in my experience, you may choose to hire an EA without involving an agency.  Perhaps you have a fantastic recruiter, or you have teammates who have EA recommendations (source from within if possible!)

If you plan on going straight to the job boards, be sure to prepare a thorough JD outlining the EA’s responsibilities and the kind of person who might be a great fit for the role.

Another helpful note:  during my time as a Chief of Staff, many of the best EAs I’ve met don’t necessarily come from Business or Technology backgrounds.  In fact, many people are trying to get their break into tech by looking for roles in operations, administrative work, and other non-technical sectors in startups.  Keep that in mind as you start your search.

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Part 3:  What to look for in an EA

Whether you go through an agency or not, what you look for in an EA should be the same.  And most of the time, this depends on what is in your EA’s scope.

If you want an EA to help free up your time from low-yield tasks, you’ll need someone with professional-level English proficiency, meticulous attention to detail, and a love for all things admin-related.

As a note:  one of my CEO coachees, Sydney Liu of Commaful, found great success in teaching his EA how to use GPT-3 to write excellent emails.  In my opinion, this is an extremely clever hack.

On the other hand, if you want your EA to eventually become a thought partner, potential Chief of Staff, or take on more of a strategic role, you’ll want to find someone who you communicate well with.

Therefore, there should be little to no language barrier, they are First Principles thinkers who can think several levels of abstraction higher than your average person, and can challenge you if they believe you are making a bad decision.

I should note:  most EAs can grow into this kind of role.  In fact, my current EA is growing into this role.  It all depends on how you onboard them, which I write about here.

You may want your EA to work in the same timezone as you.  In the past, I tried my hardest to make it so that my EAs could work asynchronously and therefore stay in their own timezone.  However, as I’ve gotten closer to my current EA, I found we worked best and had the best relationship when we worked in the same timezone on the same hours.  Please pay them well for this kind of sacrifice.

Finally, you should get along with your EA.  It seems simple enough, but having a good working relationship with them should be as important as having them produce good work.

To assess this, take the time to ask the agencies whether you can get Loom videos from each EA they suggest you work with.  Have each EA both record and write answers to these questions:

1. What’s your name?
2. Where are you from?
3. How long have you been an EA?
4. What do you look forward to most in potentially working with us?
5. What do you like to do for fun?

The beauty of Loom is that you can batch-watch all of these responses at 2x speed and decide whether you like them or not.  In fact, I recommend the 2-minute Loom video as part of every hire you make.

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Part 4:  Preparing to onboard your EA

The nicest part about onboarding your EA is that you don’t have to wait until your EA starts to begin documenting how-to’s for your EA.  In fact, I’d recommend starting as soon as you finish your Energy Audit.

Start by documenting all of the processes you want your EA to do.  In your centralized information hub (for example, Notion), create a table.  Add all of the responsibilities from your Energy Audit as a “how-to” to document.  Here’s a preview of ours (see photo...)

💡 RESOURCE ALERT:  I’ve created this template for your use here!  It’s free to download.

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As you can see, the table is configured with the following columns:

• Name of the how-to tutorial: You’ll store the step-by-step instructions within these tutorial pages.  Below is a screenshot of an example of a tutorial that I gave to my EA.
• General department within your startup: If you eventually have more than one EA, it can be helpful to sort by department so each EA knows where to find relevant information (e.g.: finance, operations, HR, etc.)‍
• Specific category it pertains to: Think of these as tags.  For example, we have a bunch of tutorials that are tagged as “Brex” because they’re write-ups that discuss how to complete tasks using Brex.‍
• Writer of the how-to tutorial: Authorship is important, because if someone has a question about one of the instructions, they can ping the person who authored the tutorial.‍
• Status of the how-to: I like to keep track of how-to’s I need to write someday but haven’t gotten around to doing yet. I do this by grouping it either as “Stable” (ready to go), “Spinning up” (in progress), or “Not started” (no content written yet.)

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There are several tools that will make your life easier when creating these tutorials.  The two that come to mind are Loom and Tango.

Loom is simple:  it allows you to record a video of yourself completing a task.  And because Loom makes it easy to organize videos well, too, I create a folder specially for my EA, which I store in the Team Folder.  The photo pictured shows an example of how I make it easy for my EA to find and reference videos as a quick refresher if she needs one.

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Tango is another amazing tool.  If your EA prefers written instructions that they can follow in their own time, this is an easy way to create step-by-step instructions without writing a single word.

Instead of just showing you a screenshot of how great Tango is, I’ve created an example of a Tango tutorial below.  Give it a try! 👇

How to make a GDocs copy and publish to web

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Part 5: The first 30 days

You’ve finally made the hire, your heart is thumping at the idea of reclaimed time, and you’re ready to pass everything onto your EA so you can run off and do other things.  All that’s left is onboarding them.

1. Be sure to give them unfettered access to all of your administrative work accounts: your calendar, email inbox, accountability tracker, and so on.  Do this using 1Password or a similar password manager.  You may feel fear, but it’ll be well-worth it and if you’ve done your due diligence properly, you have very little to worry about.
2. Give your EA access to tools that will make their life easier.  Please pay for all of these tools for your EA, and deduct it as expenses.  It’ll be well worth the cost.

I’ll do another write-up at a later date on my productivity stack, but in a nutshell, I recommend every EA get:

1. Superhuman (fast emails)
2. Vimcal (easy scheduling for availability)
3. Alfred (snippets for quick responses)
4. Grammarly (grammatically correct prose)
5. Cleanshot X (easy screenshots and video recordings for receipts, reimbursements, etc.)
6. Ramp (for company-related purchases under $100, my EA uses her Ramp card without asking me)

The only other thing I’ll add is this:  the best rule of thumb to follow when onboarding your EA is to do it in the following three steps.

1. First, your EA watches you do it once on your own as you explain it to them.  (You can take care of this by following the aforementioned steps using Loom and Tango.)
2. Next time, your EA does a first pass on their own, and then actively solicits your feedback on how they can improve.  You review their work and offer praise and constructive feedback.
3. Finally, after your EA has done it all the way through from start to finish with no errors, they’re ready to do it on their own with you spot-checking their work.

Last thing:  I’ve already previously written about how to onboard someone here, so I won’t repeat that information in this article.  Go give that a read (specifically under Point #4.)

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Part 6: Maintaining a great relationship with your EA

Congratulations!  The bulk of the work is done.  Your EA is up to speed, you two love each other, and they’re crushing every task you hand them.  All that’s left is making sure both of you are in lockstep.  To do this, make sure your EA has a great life.

• Your team should treat your EA with respect.  Do not tolerate abusive, demeaning, or condescending behavior towards your EA.  In many ways, your EA is an extension of you.  Be sure to treat them this way, and the rest of your team should follow your lead.
• As you do with your direct reports, it’s important to maintain 1:1 meetings with your EA.  The purpose of doing 1:1s is to make sure they can surface any concerns they have, and you can check in to make sure their work life and personal life is good.  An easy way to do this is to ask them Magic Questions once a month.  While doing Magic Questions, pull out Action Items from them that they can do to make their lives better, and put Action Items on your plate if there are easy things you can do to make their lives better, too.  Store these in their Action Tracker.
• ‍Maintain an Action Tracker with your EA. You’ll need to have a centralized place to track all the tasks your EA has and all the tasks you want your EA to hold you accountable for. Therefore, have a centralized place where your EA can see what is a priority to you, and you can see where you may be blocking them. I made a full three-part tutorial on how we use Asana at Mochary Method.  Give it a watch here.
• Create a channel for you and your EA to discuss things asynchronously. Your EA shouldn’t have to wait until your 1:1 meeting to surface things.  Make it easy for them to reach you and for you to reach them.  Do this by creating a dedicated Slack or Threads channel between the both of you. I’ll write more at a later date on how to best utilize Slack or Threads for communication, but for now, just have one created, and use it liberally.

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Conclusion

Many organizations overlook EAs, which in reality, EAs are the glue that hold the whole startup together.  They make all the gears turn behind the curtain and get all of the gritty admin work done.  As such, value and treat them as an equal member on your team.  If you can do this, there is nothing you and your EA can’t accomplish together.

Further resources 💡

• About the Energy Audit for Part 1 of this write-up
• My template for documenting how-to processes
• Loom for interviewing process and recording tutorials
• Tango for recording tutorials and writing step-by-step instructions
• 1Password for granting your EA access to all of your logins
• My write-up on how to onboard someone successfully
• Matt’s write-up on how to onboard someone
• Matt’s Magic Questions for doing 1:1s with your EA
• Video on how to create an Accountability Tracker using Asana in three different levels
• My article about Inbox Zeroing here, which you may have your EA do for you

Love Notes 💌

A huge thank-you goes to Trishia Pasaquian for first and foremost being my friend, and then an amazing coworker, and finally my EA.  I learned how to work with EAs because you have taught me so much.

Another special note of thanks goes to Joe Brown of Smaal, for being the inspiration behind writing this long-overdue article!

And finally, big thank-yous go to the following contributors whose ideas I’ve included above:

Sydney Liu of Commaful provided his brilliant idea using GPT-3 in emails.

Case Sandberg, CTO of Mochary Method, introduced me to Tango.

Shiraz Dole was the 1st person who taught me how to document everything using Loom.

And finally, Matt Mochary, as always, provided so many useful nuggets of wisdom.