How I trained my executive assistant to save me 20 hours a week


A few years ago I was drowning in admin work and spending my nights and weekends answering emails, catching up on invoicing, scheduling out my week and more.

I was building two companies and they were growing fast. I also had kids and a busy family. It was a full time job just to stay organized.

Things were coming at me from all angles. Travel. Meetings. Endless emails. Payroll. Bookkeeping. Events. To-do list around my house. General life stuff.

It was a nightmare and it easily took 20/hrs per week of my time.

I decided I needed an executive assistant. I interviewed several folks and a few former teachers who wanted $40-80K/yr to join me.

I couldn’t justify the expense so I held off.

Then I met Marshall Haas, the founder of Somewhere.com and I learned about the cost of offshore talent who could work remotely. He was building big businesses with only overseas employees for 80% less in payroll costs.

Over the following few years I got on this trend all the way and began also building my businesses overseas.

At the time I had around 12 employees. I was still on a tight budget. I didn't need a specialist to run my performance marketing or finance.

I needed an all-around team player. Somebody who could help me stay organized and handle the admin as well as a lot of minor business functions like payroll and bookkeeping.

Basically somebody to help me with the function of being an executive.

My very first hire overseas was an executive assistant.

Today, she is the quarterback of my life and a full on Chief of Staff.

I couldn't live without her. My email inbox is no longer stressful. She handles problems before they reach my desk. She functions like my right hand and helps me run my companies.

In this email I'm going to outline exactly how I trained my executive assistant and what she does for me.

Here’s what my EA does for me:

  1. Manages my calendar and schedule daily.
  2. Filters my emails, drafts responses, and keeps my inbox under control.
  3. Blocks focus time and protects me from unnecessary meetings.
  4. Responds to certain messages and makes sure everything reflects my voice.
  5. Does light bookkeeping, payroll and admin tasks at several of my companies.
  6. Prepares briefing documents and talking points before I do important meetings.
  7. Books all my travel including flights, hotels, cars, etc.
  8. Builds backup plans in case of delays or last-minute changes.
  9. Manages some of my expenses, reimbursements, and invoices.
  10. Takes care of personal errands like gifting, reservations, and vendor scheduling/management and payments.
  11. Coordinates family related things discreetly when needed.
  12. Handles renewals and memberships for subscriptions I have.
  13. Interacts with contractors and vendors to solicit bids (she does this a TON).
  14. Researches potential podcasts and speaking opportunities for me.
  15. Runs the HR function at one of my companies, tracking employees sick time and vacation days, getting contracts executed and more.
  16. Posts jobs and helps me recruit. She screens and interviews candidates on video so I can review. Also tracks hiring across my companies.
  17. Reminds me of valuable action items I might have missed that I need to follow up on.

And a lot more.

Needless to say, this person has completely changed my life and I couldn't live without her.

All for $2,000 per month.

Here’s how I actually trained her:

First, I recorded everything!

I used Fathom to record all of my calls and Loom to record every single admin task I did for a few weeks.

This includes email responses, how I do calendar management, vendor comms, research - everything. This wasn't just about creating training materials, it was about showing her exactly how I think and operate.

I dropped each recording (loom link) on a Google sheet, organized by task.

I think the best way for an EA to learn how you like things to be done is to shadow your day to day to see you in action. This accomplishes that.

Give her tasks within your company:

The best way to develop a strong employee is to push them.

When something needs done and you think she could potentially handle it, give it to her!

For me this included tax prep, bookkeeping, payroll, HR function, gifts for my son, family trip planning and more! I'd simply hop on a call with her and show her how to do it or record a loom video and share it.

If you hire an EA and you are too lazy to train her, send her tasks, and work with her, she won't be able to develop and add value.

You get what you give!

Send a ton of voice notes:

When I would think of something she needed to help me with, I would record a voice note explaining it and I would send it to her.

This is massively efficient and I still do this almost daily today.

Communication:

I also created a document with my communication guidelines which covers:

  • How I write emails (short, direct, action-oriented)
  • My calendar rules (no meetings before 8am, block Fridays for catch-up work, spontaneous huddles with my team)
  • How I prioritize my business activities (revenue-generating initiatives come first, always)
  • My communication pet peeves (don't say "just following up" - just tell me what you need, etc)

This document saved us both dozens of hours of back and forth and it took me 15 minutes to create.

Soliciting Bids and Home Repairs:

Recently I needed gravel delivered to one of my properties to help with erosion control.

I pulled out my phone and recorded a 90 second video walking through and pointing at exactly what needed done and sent her the video.

She uploaded an "unlisted" version of the video to YouTube so we could share it with contractors and they could watch it on their phones, etc.

She then did online research to build a list of 5-10 contractors. Called them all and talked them through the project. Sent them the video so they could understand it.

She spent the next few days getting bids and even giving some contractors access to my property to come see the job in-person.

She sent me a google doc 5 days later with the bids outlined and her recommendation to hire Watson Trucking for $750 for a load of fine crush gravel, spread.

I gave her the go-ahead, she signed the proposal, the gravel was delivered, and she cut them a check for the service out of my account.

I literally didn't do anything at all except give her the thumbs up and the work got done.

She did the same exact system to solicit bids for garage doors at my storage facility, a whole home filtration system, and a plumbing repair I needed at my industrial property, and even a mountain bike I wanted as a birthday gift for my son.

This is a GAME CHANGER.

A note:

I had a previous executive assistant located in the Philippines and unfortunately she couldn't get contractors and vendors to trust her. They could sense by her accent that she wasn't in the states and would require talking to me for many things.

The South African accent (mine is British) solved that for me which was worth it.

Why I Chose South Africa:

South African EAs speak perfect English with a British accent. They understand US business culture and work for $8-12/hour. Many of the professionals there have worked for US companies before and are completely fine working EST or PST hours.

My EA had 17 years of experience helping executives in South Africa before I hired her and types 75 words per minute.

She has done this role for almost 2 decades and worked across finance, software, and the music and entertainment industries all for CEOs.

She knows the ins and outs of executive level communication and was willing to join me for just a few thousand dollars per month.

My EA makes $2,000 USD per month, or about $12 per hour all-in.

She is in the top 1% of income earners in South Africa.

Granting access:

When she first started, I didn't give her access to make payments or my personal email right away.

I set up a second email address with a forward in place so every email I received also went there. And I gave her "send mail as" permissions to draft certain emails on my behalf.

We used this system until I got comfortable with her decision making and trustworthiness.

I use an online banking system called Ramp and RelayFi for my company accounts to make payments. I issued her own virtual card here with low limits. I did the same for my personal account, a card number with its own tracking and limits.

Over time, as I got comfortable, I let her into my personal email and set up a limited user in bank accounts for bookkeeping, etc.

Some people think this is risky. I don't find it any more risky than hiring somebody from the USA to help you manage these things. I also set up 2FA on every online login so I knew when she was logging in and out of my email and banks and she wouldn't be able to move money or download information without me knowing.

How I found her:

You have two options for finding an EA.

1) Do it yourself.

Post a job on Linkedin in South Africa, Colombia, Philippines, Brazil and Sri Lanka (these are the best locations). Sponsor each job post with $50 per day and let it run for 5 days.

The Philippines is the most affordable (can hire for $4 an hour). Brazil and Colombia are on our time zone and have excellent talent. Sri Lanka has good english and is almost as affordable as Philippines. South Africa is a bit more expensive but the english is superb. If you need a lot of live communication like I do I recommend SA.

You'll have 1500 applicants in 5 days. Send them all a typing assessment and don't waste your time interviewing anyone who types under 50 words per minute. How can somebody work remotely if they can't type fast?

I've found this to be the #1 indicator of success. Find a fast typer! I love legal assistants as well (my EA is an ex legal assistant).

Once you get the fast typers, ask the rest of them for a 1 minute video introducing themselves. You'll be able to judge the professional maturity and english communications skills with this.

You'll be left with 2-3 decent candidates. Interview them and hire one!

2) Use a service like Somewhere.com to help you find a killer EA.

They do the typing assessments, offer EA training, background checks and more for you. They also can source equipment to make sure your EA has a great workstation.

So if you want to hire someone like my EA, you should talk to Grant who is the person who literally sourced her for me.

Grant works for me at Somewhere and has helped 100+ business owners hire executive assistants like mine this year alone. He’s one of the people I trust most when giving advice on this role.

I asked if he’d be willing to do 10 calls this week with founders or executives who want to know more about how they can hire their own EA. If you want to talk to him, you can do that here.

It won't be a sales call. He'll educate you on the best plan of attack, the options in the world, the budget that would work best in each country, answer questions about work setup and how it works, and more.

Ask him about regions, compliance, time zone, tools, and more. I guarantee it'll be worth your time.

My advice to you on all of this. Start small:

Don't try to train someone on everything at once. I started my EA on just email and calendar management. Once she mastered that, we added more responsibilities.

Consider sharing an EA with a friend or another person at your company. Many of the best folks can easily do these tasks for multiple people.

I treat my EA like any other business partner because that's what she is to me. She knows my goals, understands my priorities, and has the authority to make decisions on my behalf.

I focus on strategy and growth while she handles the admin side.

I literally can't imagine running my businesses without her. I hope this email helps if you already have an EA or plan to hire one soon.

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A few posts from this week:

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Nick Huber
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Nick Huber

I own a real estate firm with over 1.9 million square feet of self storage and 45 employees. I also own 6 other companies with over 400 employees. I send deal breakdowns with P&Ls. Newsletter topic: Real Estate, Management, Entrepreneurship

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