Assistant to the AwkEng

Hi all!

I've mentioned briefly in a few previous blog posts that I work with a personal assistant. Some readers expressed curiosity about this, so today's post is about my experiences and advice on finding an assistant and how we work together.

Why work with a personal assistant in the first place?

The whole reason for hiring an assistant is to leverage your time. I hired an assistant a few years ago when I had an hour plus drive to and from work. That was two hours or more lost a day when I couldn't work as usual, but I could talk on the phone, dictate things, and answer questions. Working with an assistant was my attempt to claw the time back.

What does my assistant handle?

Basically, if it can be done with a cell phone and the internet, it can be delegated to my assistant. The bulk of what my assistant handles involves running my CRM, following up on calls, and scheduling. It's something I know I would drop on my own, but my assistant helps keep me on track. In a way, its a form of an accountability mechanism, sort of like hiring a personal trainer to make sure you go to the gym.

Aside from the CRM, my assistant also handle a lot of tasks that are heavy on "follow up". For example, I organized an ice cream tasting event several weeks ago that involved calling 4 ice cream shops in Somerville, getting pricing for tasting sized servings, and confirming they were ready the weekend of the event. It sucks up a lot of mental space, especially if a shop is only open at certain times, or the manager is only in on certain shifts. Tasks like that (calling venues for birthday party package rates, calling architects to see if they're taking on new clients, rescheduling the dentist, etc), are perfect for an assistant.

My assistant also handles a number of small research projects. For instance, working with the Veteran's Administration to find the WWII service records for my grandfather.

Finally, I review the status of some of my own personal tasks with my assistant, which keeps me honest and on top of things.

How do we work together?

Typically, I do a 10 minute phone call in the morning with my assistant, either while commuting to work, or during the pandemic times, while doing chores around the house. The typical routine is to check items we've snoozed to see if they've come up again. If the ball is in someone else's court, we'll check if it's due yet for a volley back and will ping it if needed, then we run through active projects, then quickly run through dictation on anything in the CRM system.

My assistant has access permission on my calendar, my blog, and a few other systems, usually managed through regular account permissions whenever possible, or otherwise through a password vault. I've set up permissions for an email alias, so messages can look like they came from my assistant, or they're can be made to look like they came up from me. (Note, this doesn't grant broader email read access).

When Interrobang was running full steam ahead, we'd have a call every morning, but now we typically check only two mornings a week (hint: she has capacity for additional clients!). I actually looked back at the meeting load for Interrobang, and I think my assistant helped me set up 132 meetings or video calls over the span of several months.

Finding an Assistant

I went through a few assistants before I found one I've worked with for the last few years. Here are some of the options for finding one:

Starting in maybe 2018-ish, "AI" powered assistants were really trendy. Turns out, it was a giant "wizard of Oz" demo, where they had real people behind the curtain pretending to be the AI while the engineers frantically tried to use that behavior as a ground truth for a data set so they could learn and automate everything to reduce costs. Those didn't work so well and most of those are shut down. Not a recommended option, but those are out there.

Another option is to work with an agency. They typically have lump packages for a fixed number of hours of work each week, they'll assign an assistant to you, which means they'll take care of the vetting/hiring/etc. I tried this for a period of time, but the assistant assigned to me quit with the agency, so I went looking again.

Finally, you can find an assistant via a freelance site, like This ranges from $3-5/hr call center employees in the Philippines, to $10/hr assistants in Latin america, or US based assistants at $30-90/hr. ($90/hr is for executive assistants for big company CEOs). In my experience, you get what you pay for, and the most important thing I was looking for was evidence for good soft skills. And yes, this means you'll need to put up a job post and screen resumes. This is my recommended route.

I had an assistant out of Jamaica for a little while (only the mildest hint of an accent), but her experience was mostly working in help support call centers, and she lacked some of the soft skills to anticipate needs and tone when following up on tasks. My current assistant was formerly a paralegal (strong indicator for soft office skills), is US based and in my time zone, and has been awesome. So you it might take a little while before you find someone you like working with.

Closing Thoughts

When I look back and ask if the time with an assistant is worthwhile, it's less a question of "did I feel like it was working" and more like "would I have gotten X done at all?" In terms of the CRM, which has gotten me my last several jobs, I know for a fact that I'd let it drop when I got busy or stressed.

I'm a big believer in systems, and working with an assistant is part of my system for making sure certain things absolutely get done.

best regards!
aka THE Awkward Engineer

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