Assistants: Not just for the boss anymore.

This is not strictly software-development-related, but a number of developers have asked me about my experience finding and working with a remote assistant. I’ve had my assistant for a few months now and I thought I’d jot down some notes on the experience.

The V-word

First, let’s get one thing out of the way. I despise the term “virtual assistant”, along with “virtual team” and “telecommuting”. I’ve been working from home for years and there’s nothing “virtual” about the work I do. The same goes for the work I delegate to my assistant. She may be “remote”, but the work is very real. This may seem like semantic quibbling, but if there’s one thing I find most developers can agree on it’s that using the right names for things is important.

Assistant… isn’t that something executives have?

This was my problem for the longest time when I would consider the idea of getting an assistant. When your time is largely filled with communication—email, meetings, calls, travel—it’s easy to see where an assistant would fit in. But for someone whose work consists primarily of making things, where would an assistant be able to help? I knew I needed to do something to lighten the load, but it wasn’t at all clear if an assistant would help.

What finally convinced me to start looking for an assistant was the problem of appointment scheduling. I’ve found myself booking more and more appointments—consultations, team meetings, remote pair-programming sessions, interviewing people for Wide Teams, or, occasionally, being interviewed for other podcasts—and the constant back-and-forth email tag to set the meetings up was stressing me out. I tried all the automated solutions. Tungle, Google Appointment slots, BookingBug, YouCanBookMe, you name it. They all sucked in their own special ways. None of them could learn my own special preferences: for instance, while a day might have six open “blocks” in it for an Open-Source pair-programming session, if someone books one of those blocks, I don’t want any more blocks booked that day.

I realized that the bottom line was that there’s just no substitute for a human being who can learn my habits and trade emails with people.

So initially I set out to get someone to handle my calendar; with the hope that once I had an assistant, I’d think up more stuff I could delegate to them. Which is exactly how it turned out.

Finding an assistant

There are a number of V***ual Assistant agencies around these days. I opted to skip them and look for someone on ODesk. I did this for a few reasons:

  1. I had had a good experience hiring people for small jobs on ODesk in the past.
  2. I’m a cheapskate, and I wanted to cut out the middleman.
  3. Ideally, I wanted to establish a relationship with a real human being, not with an agency.

So I put an ad up on ODesk explaining what I was looking for an assistant. Predictably, I got a dozens of responses. I began to think I needed to hire an assistant just to go through all the assistant applicants.

Most of the applicants were in the Philippines, India, and South America, with a smattering of Americans and Europeans. Then one day I checked ODesk and was startled to see an applicant from just a few miles up the road in York, PA. Intrigued, I replied, and that’s how I met my assistant Mandy.

As it turned out, it was not purely the result of wild chance. ODesk is syndicated by various job sites, some of which localize their listings based on the location of the job poster. Mandy had seen one of these listings, and created an ODesk account to respond.

Philosophically I am sort of a combination localist/globalist: I have no problem with sending my dollars overseas to workers who need to feed their families every bit as much as Americans do. To my mind there isn’t a great deal of difference between hiring someone in Detroit and hiring someone in Korea. But I do believe in participating in the really local economy as much as I can. That is, local as in we-could-meet-up-for-coffee local. So I was excited to see a nearby applicant.

I conducted a short interview over video chat. Once we established that both of us were real people and not Internet scammers, I decided that the best way to figure out if she was a good fit was just to start throwing some tasks at her for a week or two and see how she did. With ODesk you there’s no commitment and you only pay for the verified hours worked (and you can set a weekly cap), so this wasn’t a huge risk.

Mandy has been helping me out on a part-time basis ever since, so obviously it went well.

What my assistant does

Here’s a sampling of the work I delegate to Mandy. My biggest roadblock to hiring an assistant was figuring out what I would be able to delegate to them. If you’re pondering the same question, I hope this list will help you get a better idea of the sort of tasks you might be able to turn over to an assistant.

  • Scheduling. She has write access to my calendar. If someone wants to make an appointment—e.g. to schedule an Open-Source pairing session—I forward it on to her and she makes the arrangements and makes sure they are all set up with Skype etc. before the meeting. She can see my calendar and knows my daily routine, so she’s able to make appointments with zero “is this date/time good for you?” back-and-forth. She also sends out reminders and confirms that the other parties are still able to make it to the appointment.
  • Every Monday she briefs me for about fifteen minutes over Google Talk, reminding me of any appointments or other commitments I have for the week. Yes, in theory, I could see this stuff on my calendar; but I’m notorious for forgetting to check it.
  • Customer service: if any one has a problem with a book order I pass it along to her. She has access to my storefront account and is able to resolve most problems without any further intervention on my part.
  • Blog maintenance: if an old post of mind starts attracting a lot of spam, I send it to her and she cleans it up and shuts down comments.
  • Lots of similar blog maintenance tasks: for instance: today I had her pull down all of my old Blip.tv-hosted screencasts, put them in Dropbox, re-upload them to my new video host, and edit all the relevant blog posts to embed the new video widget.
  • I had collected half a room full of mouldering computer hardware over the years, and it was keeping me from rearranging my office. She researched local computer recycling centers, and arranged to have a local acquaintance of hers come and haul the hardware away for a small fee. Stuff like this is one of the reasons I like having someone local, with local contacts.
  • I wanted to know if it was cheaper to have a local tire shop buy a set of tires for me, or to order them online and have them shipped. I had her do the online research and call the tire shop to get a quote, saving me the time.
  • She did a bunch of research for me for my (sadly canceled) trip to Poland. She looked into international phone options (including determining if my phone was international-capable), researched credit card foreign transaction fees, determined that I didn’t need a visa to travel, etc.
  • Billing: She sets up and sends invoices.
  • Record keeping: Some clients don’t go through my usual invoicing channels, for one reason or another (e.g. Code Benders does direct deposit). Mandy keeps Freshbooks up to date with these nonstandard payments.
  • When I prepare a new version of Objects on Rails, I send it to her and she types up the changelog, sends out the update, and notifies the mailing list.
  • When people send me errata on the Objects on Rails mailing list she creates a ticket so I don’t lose track of the issue.
  • She tracks the names of everyone who contributes suggestions, errata, and other comments to Objects on Rails. Then she uses Github’s online file editing to update the acknowledgments section, which then gets rolled into the next release.
  • I’m bringing her up to speed on audio editing, with the aim of turning over the podcast post-production duties for WideTeams.com to her.
  • She helped me prepare this list!

Tools

Here are some of the tools that have helped me work with an assistant.

  • Google Talk: For voice, video, and text chat.
  • ScreenR has been instrumental in enabling me to quickly demonstrate how to perform various tasks.
  • Google Docs for sharing notes, instructions, results of research, etc.
  • LastPass Enterprise for securely sharing credentials to assorted online services, such as my storefront provider.
  • Dropbox for filesharing.
  • I’ve started using Astrid for task tracking. The Android and Web UIs are both quite nice, and I can just include Astrid in the TO line of an email in order to create the task and automatically assign it to the primary recipient.

Do you need an assistant?

Some people are going to be able to make better use of an assistant than others. If you have a simple write-code-all-day routine, you probably wouldn’t get much benefit. But if your life is more complex, with a lot of different people asking for your time, and an increasing number of administrative headaches that fall outside the core of your craft, you might find that an assistant frees up enough of your time to be worth the investment.

Hire my assistant!

If after reading this far you’ve realized that you could benefit from the services of a remote assistant, I have some good news: my assistant, Mandy Moore, has authorized me to announce that she currently has availability to take on more clients. You can find her ODesk profile here. She’s relatively new to the remote assistant trade, but she learns fast, gets things done, and has been a real pleasure to work with. I wholeheartedly recommend her.