How I Work With My Assistant To Save 80 Hours Per Month

Mar 7, 2019

I finally hired an assistant and it changed my life. Buying back your time by offloading extra tasks is the holy grail. Making it work can be tricky though. Here’s how I did it.

(If you're looking to hire an assistant, give my company Shepherd a look.)

I like to work on a lot of projects. Here’s what’s on my plate right now:

  • I’m the CEO and owner of several companies
  • I write this blog
  • I’m planning a course to teach others how to make physical products
  • I oversee a couple of private investments and research new opportunities as they come.
  • To top it all off, I’m a new Dad to a baby boy

Needless to say, it’s easy to fill my time. With so many projects happening at once, there’s a lot of little things to take care of every day. I don’t actually like to feel “busy” though. My preference is to free myself up as much as possible to explore new projects and leave the nitty gritty details to my team. This isn’t always possible, but it’s what I strive for.

Recently I’ve been able to “buy back” about 60 hours of my time each month with an assistant. In this post, I’ll cover how I got there and how you can too.

  1. My many false starts with hiring assistants
  2. The key to finally making it work
  3. What my assistant does for me
  4. How much my assistant costs
  5. Where I hired them
  6. Best practices

Failures in hiring an assistant

Ironically, I’ve been able to successfully hire employees for various processes in my businesses. However, hiring an assistant to help directly with my own tasks has been a struggle for me.

Until recently, I kept failing to keep assistants. I’ve tried…

… and everything in between. Ultimately I would cancel any I tried after a few weeks or move them into a team at one of my companies (work that has nothing to do with my direct tasks).

I repeated this cycle for years:

Get excited by the idea of offloading mundane tasks -> hire an assistant -> get annoyed at how it felt like more work than the time it saved me -> cancel -> repeat.

Ultimately I never stuck with hiring someone to help me personally. Looking back, I was the problem. Not the assistants I hired. Why did I struggle so much with hiring someone for myself?

In a word: access

What made it finally work

When I hire an employee to do a job, they need access to company information and our tools. It’s step #1 for getting them setup to do a good job. You’re probably saying “duh”.

However, this was the overlooked reason I kept failing with assistants

I just wouldn’t give them enough access to my personal and company information. It would feel like more work than it was worth to catch them up and explain everything.

They wouldn’t be looped into email threads, they wouldn’t be part of the initial conversation, and they wouldn’t have the access needed to be great. It was a failure of design, not competence.

The more you can integrate an assistant into your team, the better. Here’s what I mean:

Giving your assistant deep “access” is key to making it work

To illustrate what a great assistant relationship looks like, let’s set up a hypothetical project and see how it’s worked through in 3 levels access.

A hypothetical project scenario:

A new project just landed on your plate. You’re going to begin selling your e-commerce products through a new distribution channel your company has been invited to. You need to launch on the new channel in 60 days. The new channel has unique requirements that differ from your current channels. Things like:

  • The new channel requires all product photography to be on a white background. Your existing photos were shot on colored backgrounds so you must re-shoot everything.
  • Tweaked copywriting is needed based on the channel’s character limits and page layouts.
  • You need to order more inventory to have enough for the new channel.
  • Your inventory needs to be labeled differently to work with the new channel’s warehouse.

Here’s how it would go down working with an assistant in 3 scenarios: “bad”, “good”, and “great.

What a BAD assistant dynamic looks like

Kickoff: You get out of the project kickoff meeting and have a stack of tasks that will be required to launch the project. You want to fill your assistant in but you get distracted and forget. Days later you remember and schedule time with them. You meet 2 days later and then spend 30 minutes filling them in on the project.

Task Assignment: You then have to think through what would be efficient for them to handle vs yourself. You decide you’ll have them look for a new copywriter to help tweak things. The other stuff will take too long to explain so you opt to just do it yourself. They’ve never worked with your warehouse team before, and have no clue who you use for design.

Information Flow: 4 weeks into the project the new channel changes their design which means new character limits for your product page copywriting. You have to relay these changes to your assistant again.

What a GOOD assistant dynamic looks like

Kickoff: You get out of your new project meeting. Later that day you have your standing weekly catchup meeting with your assistant (that’s pre-scheduled for the same time each week). During the meeting, you fill them in on the entire project.

Task Assignment: You introduce them to your warehouse team and photographer contractor team and explain what is needed. They run point on it from there.

Information Flow: You begin looping them into email threads with you so your assistant is in the know when updates and changes arise. When they do, you delegate those changes to your assistant.

What a GREAT assistant dynamic looks like

Kickoff: You don’t have to spend any energy catching your assistant up on the project because they were in the initial kickoff meeting from the start. (or even better, they took the meeting on your behalf)

Task Assignment: They run point on the project for you. They already speak to your warehouse and photography teams regularly so kicking off new tasks with them is a breeze. They’re a part of your team so everyone knows them already.

Information Flow: Your assistant keeps you updated with progress and changes. You’re free to focus on other projects.

Getting to the “great” scenario takes time, patience, but most importantly access. They need to know how your company works and who to go to for various things. They should be on the inside of your life and company. Set things up so information flows to them naturally.

The key point: don’t be the informational bottleneck to your assistant.

Meet my assistant

My assistant’s name is Carin. She works with me remotely from her home (as does everyone on our team now).

If you're looking to hire awesome yet affordable talent, give my agency Shepherd a look ( We're a head hunter agency for finding top overseas talent.

Time & Cost

I started off by working with her for 2 hours per day for a total of 40 hours per month. After about a month together I decided to bump that up to 3 hours per day for a total of 60 hours per month. She’s extremely productive so I truly get 15 hours per week of my time back.

Update: She now spends 4 hours of her day with me, for a total savings of 80hrs per month.

How much access I give my assistant

Carin has a ton of access. She has all of my credit cards and knows when to use each. She has many of my logins to be able to communicate on my behalf.

Everything is shared securely through 1Password. I’ve set up specific vaults that are only between us so I can control which things she gets access to and which only I can see.

I’ve separated out bank account login info into a new vault that only I have access to. Other than that I’ve shared access to the majority of my personal stuff along with most company tool logins. She’s in Basecamp with the rest of my team and is encouraged to interact with anyone.

What my assistant does for me

Below are some recent projects Carin ran point on. I’ve also included on-going tasks I delegate to her. Not everything I delegate is mundane stuff that I don’t want to do. I also delegate things I enjoy but simply need extra help with.

1. Coordinate the sale of my rental property

I’m in the middle of closing on a rental property I’m selling. The property is in St. Louis but I’m currently in Italy. Closing on a property while out of the country is difficult. Carin covered everything.

We learned I would need to go to the US consulate in Milan to sign the documents in front of a notary. She scheduled everything and coordinated with the title company. I just had to show up and sign. The process was a pain in the ass (read my tweet thread on this), but she perfectly coordinated everything.

Little things like coordinating inspectors were handled by her as well.

2. New product launches

I lead new product designs at Peel. However, there’s a ton of repetitive stuff that goes into launching any new product. Carin coordinates photography, product page layouts, programmers, and even writes product page copy. She’ll work closely with my head of operations to figure out warehouse logistics and launch timelines as well.

3. Run point on new business partnerships

Remember that hypothetical project I outlined above? That’s actually a real project of ours she’s in the middle of leading right now. There’s a ton of moving pieces and she’s overseeing the whole thing. She’s been coordinating everything with our team and keeping our contacts at the new distribution channel in the loop.

4. Travel planning

My wife and I are now living as nomads for all of 2019. We’ve been staying in Airbnbs for anywhere between 4 days to 4 weeks Most months we stay in one place at a time. However, this month we’re going all around Italy. Carin helps coordinate and book accommodations, flights, trains, car rentals, and everything in between.

She keeps an eye out for gaps in our travel plans as well. Just the other day I almost forgot to rent a car. Little details like finding a gym ahead of time were taken care of.

Recently I heard the AMEX Platinum card was adding Global WeWork access as a free perk. She kept checking if it was available every few weeks. Once it was, she signed me up and saved my access to 1Password. It was seamless

5. Personal bookkeeping

I track my personal finances in a robust spreadsheet. Each Monday Carin spends time categorizing transactions into their respective categories. Once it’s done she pings me and I check how I’m tracking for the month. She also texts an update of our spending to my wife.

6. Personal bill pay

Random bills and notices come my way all the time. The other day I received several random medical bills for blood work done a few months back. Going through phone trees to pay a small bill is horrible… so I sent it over to Carin and forgot about them. She knows to pay them with a specific credit card of mine.

In Italy I’ve gone through road tolls that bill your license plate later. She has a reminder to check the toll website and add our license plate to find and pay our tolls once they post. I can forget about it.

Final thoughts

If you’re in need of an assistant, I recommend my agency Shepherd. We find amazing full-time overseas staff for small businesses. Below are my final thoughts and tips on hiring an assistant to save time.

  1. A great assistant is a great project manager. My assistant can handle projects from start to finish.
  2. Trust your assistant with a ton of access. Don’t think you’ll trust a candidate with deep access? Hire someone at a higher level that you do trust.
  3. Schedule weekly check-in meetings with your assistant. This serves as a way to get updates, give input, and to hand off new items. Do this at least once a week so you get in the habit of delegating. I HATE meetings – but this is an exception I make. Employees should be fairly autonomous but an assistant is linked to you.

You can tweet at me or comment below with any questions or comments.

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