Working with a Virtual Assistant

As part of my evolution as a leader, better managing my balance between individual contribution and delegation/leadership was necessary. At the same time, my schedule was only getting denser and inbox overflowing.

So in August of 2014, I hired a VA – a virtual assistant. For privacy I won’t mention his name or embarrass him too much!

I’m going into detail here because I believe working a with a virtual assistant can be, from my experience, a huge advantage at an incredibly reasonable price. So I want to relay how I worked through it in the hope that it helps you.

Hiring
Like many other initial tasks at Contactually, I started off with ODesk. I limited my search to the US only – I wanted a close enough time zone, and to eliminate any risk of a language/cultural mismatch, especially if they are going to be acting on my behalf. The initial search wasn’t too strenuous – ODesk makes it easy to quickly filter out the top candidates. I set up 15 minute Skype calls with the top ~six candidates, where I learned about their past experience, how they organize themselves (looking for specific keywords they mentioned), and answering any questions from them. As it turned out, the top candidate at the end of the interview process, completely by chance, mentioned that he had been using Contactually for a little while, as his other client was a power user I knew. Small world.

Ramping Up
Ramping up was pretty easy, rather than spend large amounts of time trying to figure out what to do, I took a “figure it out as we go along” approach. The biggest decision was to give him access to everything – I believe a good personal VA needs to know everything. So that was email, calendar, Google Drive, Dropbox. This gives me the ability to simply relay what’s in my head, and he almost never has to ask to whom or what I’m referring to – he knows it. I still kept my non-work email private, and made an internal decision that personal tasks (e.g. flowers + dinner, etc) would still be just that. We established common communication channels – Hipchat (our team chat tool), Text/iMessage, email, and if need be, phone call.

Tasks
As I mentioned above, I didn’t define all these tasks initially (I honestly wasn’t sure what we would be working on together), but as they came up, I found it clear to delegate to him.

• Email management – Daily, go through email, remove anything that’s not important or relevant to me. Certain email flows (emails from users asking for support, intros from AngelList, etc) get handled appropriately. Mark the emails that seem particularly important. Oftentimes he’ll ask me on Hipchat for an answer to a question someone’s asking, or how to handle something. Many times emails can be handled by forwarding to him with a short line “sign me up for this” “put this on my calendar” “remind me.”
• Calendar management – My calendar is getting pretty insane (NOT a humblebrag). He helps me structure my calendar, move around events, block off time for certain tasks, handle conflicts, and in general, gives me the faith that I can just look at my calendar a day or two ahead and work through it. I do around ~20 screening calls a week with job candidates, and most of those can be handled via ScheduleOnce, but any other meeting request or introduction, I can intro them to my VA and he will handle from there (or he will see the incoming request and, with a quick ask on Hipchat, handle). And of course, be able to quickly rearrange things if I have to cancel or reschedule for any reason.
• Repetitive tasks and executing processes – Having someone who is incredibly organized and processed driven is crucial here. There are numerous repetitive processes that he’s able to handle (e.g. exactly what needs to be done after I complete a screening call or when a new hire verbally accepts), or multi-step processes that need to happen. I can bang out a quick email to him with what needs to be done, and clear my mind of it.
• Other one-off tasks – By keeping open lines of communication, there are a flood of other tasks he’s able to offload from me. Placing orders, getting quotes, transcribing emails/meeting notes, grabbing files for me, answering questions, etc. Text message and phone calls help when I’m out of office. I’ve also given him permission to act on my behalf for other people in the company, and periodically he’ll help other people in the company with their needs.

The leverage I’ve been able to achieve, both in terms of time and attention, has been absolutely worth it.