Third Time’s the Charm: How we Found our Amazing Virtual Assistant

Third Time’s the Charm: How we Found our Amazing Virtual Assistant

Everyone talks about how “easy” it is to hire Virtual staff – and how it’ll make a world of difference to your business.  And I get it!  If a virtual assistant could also clean my house, do the laundry, and track down that evil squirrel in the backyard, well, I’d be all over that.  But it’s just not as easy as Tim Ferriss makes it sound (sorry Tim, you know I love ya.)

Here’s my story.  Over three years it took us three tries to get it “right”.  We probably spent several hundred dollars and dozens of hours on folks that didn’t work out.  But it was a great learning experience that taught me a lot about communication and working well with people.


First Attempt: ~1 Month after Reading 4 Hour Workweek

Attempt 1

We hired our first VA in 2010, knowing we needed help with several things. This was through an agency online and there was a minimum of 10 hours a week. This experiment was a total failure because:

  • We hadn’t really thought through the exact things that we would ask the VA to help us with in advance, and estimated the true workload.
  • As a result, we didn’t have enough for her to do
  • We were rushing to give her more things – and were unprepared to do so. Our training was rushed and incomplete, and her work was therefore unusable.
  • We ended the contract after one month.

Please note: I quickly realized that we did a poor job of planning & didn’t have enough work for her. I did not realize how much of the problem was my fault due to not enough time and dedication to complete & thorough training.



Second Attempt: Odesk 101


About a year later, I tried again on Odesk. She was $3 an hour, and was one of about a hundred people who applied for the position. I narrowed the list of candidates down to 2, then had skype interviews with both. While both were very well qualified, our new VA was able to help us with phone calls to the USA if needed, and that won her the contract. When I hired her, I prepared a long list of tasks, but also made it clear that the contract was hourly – having been burned by the weekly minimum before.

Things started very well, but I did end up ending the contract after about 6 months. Here are the lessons I have learned:

  • I dedicated loads of time to creating very detailed yet complex training documentation, and emailed it to her. She tried her best, but found it confusing.
  • I relied solely on written communication – but some tasks really needed video to explain them well. As such, it took several tries to get things right. If I had created detailed documentation AND had a video, I think things would have been better.
  • Many of our processes just weren’t defined enough to outsource at that time. In my opinion, you yourself have to document a process & do it the exact same way at least three times to ensure it really is repeatable before trying to outsource. Why? Because I ended up rewriting that super long complex training documentation three times! What a waste… I should have documented at a high level, done the process enough times to get it really repeatable, THEN dedicated the time to fully documenting & training a VA.
  • I tried to send her 10 hours of work all at once. (I basically just emailed her a stack of training documents) I think this was intimidating and daunting, and meant that instead of learning one thing at a time, she tried to learn everything all at once, and didn’t learn any of the processes well.


Third Attempt: Virtual Staff Finder


Our third attempt was using Chris Ducker’s Virtual Staff Finder service. It’s not an agency – just a “headhunter” service. It’s also (in my humble opinion) very expensive, at $500 per search. (It was $400 when I went through this process.) VSF only hires part- and full-time VA’s, not folks looking to work hourly.

Once you hire your VA you will not have any reason to speak with them again (until you’re in the market for another VA.) I do believe they offer a 30 day guarantee, (where if you are unhappy with a hire they will help you hire a replacement VA.)  But if you’re interested in adding to your team, that’ll be another fee.  (Which makes sense!  They are doing the work again, after all.)  If you have a task your VA can’t do, then you’re stuck – you’d have to hire a new VA, train your existing VA, or do it yourself.


Back to the story!

Around September of 2013 I felt that our business processes were starting to get more defined and repetitive, and we had lots and lots of work to do. I’d also had some time to be introspective and realize that with the 2 VA’s I’d had – I was the common denominator! So I decided if I was going to sink $400 in finding a VA, I needed to be extremely prepared and think very carefully about how I was going to make sure this time was successful.



Here are the things I did before even contacting VSF:

  • Create a calendar of weekly tasks <img style=”width:100%;”  including an estimate of how long they would take. I used this to ensure we actually had ~15 hours a week of repeatable tasks, leaving the other 5 for one-time requests. (We’d be hiring someone for 20 hr/wk)
  • For tasks I wanted to outsource, I documented them, then followed the documentation myself a couple times to ensure they were clear
  • I got a head start creating training videos which I would send to the VA once hired
  • Looked through this website. I didn’t buy any of their info products, but I did leverage a lot of the free resources. This information was super useful to really understand key cultural differences that will affect your working relationship if you’re not aware of them.
  • Put together many hours of one-time simple tasks with full training videos.  I knew it’d be too overwhelming to give our VA 15+ hours of “recurring” tasks all at once – so I made sure we had a backlog of simple one-time tasks to do as we ramped up on the more complicated, recurring tasks.


Hiring with VSF:

Once I felt I was ready, I bit the bullet! I sent the inquiry and the process started. Initially I was a little underwhelmed by VSF’s service… they made several little mistakes like putting someone else’s name in the address line of emails to me, etc.  They sent me some forms to find my preferences and I informed them of my additional requests (as mentioned above.)  Then they went away for 2-3 weeks, (but informed me this would happen.) As a side note, I did NOT ask for references at this stage but wished I had.  I asked later which caused a delay.

When they returned, they had 3 candidates with resumes, English proficiency tests, a questionnaire and the results of my 2 additional tests. Two of the three candidates had a lot of applicable experience, and one not as much. The packets also included the VA’s preferred working times & requested monthly salary.

I set up skype interviews with all three candidates. Again, the two candidates with experience were vastly better than the third, who was nice but unfortunately lacked the experience, skills and English proficiency that we needed. During the interview we also discussed things like their working environment (quiet office or noisy house?), preferred working hours, and some logistics of preferred payment. (All of the candidates preferred Paypal, which was nice and easy for me!)

I narrowed it down to the two stronger candidates, and it came down to skill sets. One had technical skills, like HTML and css, but really scrimped on the rum vs. whiskey research. The other had very little technical experience skills but really did a very thorough job at the research – something that’s very subjective.  As a result, we decided to hire the second candidate, knowing I can always ask for HTML / CSS help on short-term contracts on Odesk or Fiverr.

This was the best decision I ever made! Our new VA thinks creatively and subjectively, which has proven her greatest asset.  As a result she can handle research projects that cannot be perfectly defined (“Please find 5 Summer Cocktails with Cognac in them”) and succeeds brilliantly.  I would strongly urge you to include some sort of subjective task in your inquiry as well.

Once our hiring decision was made, we notified VSF and they took care of informing all three candidates. At that point I reached out directly to our preferred candidate (whose email I now had) so we could start our contract. We officially started about a week later.


Onboarding and Training:

After two failed attempts to bring on VA’s, I was determined to make this work! I found that this strategy has been incredibly effective:

  • As previously mentioned, give your VA a couple long, easy tasks. Spreadsheet research or something. This will keep them busy as you get them up to speed on the long-term recurring work.
  • I gave her weekly tasks to help her learn about our industry. I ask her to read an article about Mixology every day, and to do 1 lesson in the HTML course on CodeAcademy each week. This is because our relationship is intended to be long-term, and I think it shows her that I mean that!
  • For the first 4 weeks, we met every single morning for 30 minutes, and I would teach her one more task (or step for larger tasks) – usually using screenshare. I’d also assign her a task in Asana for the task with detailed steps listed therein. That night, she’d do the task and we’d check in the next morning on questions. This proved extremely effective.
  • I asked her to send us an email summary of her day’s work every single day. She still does this and it is extremely helpful.
  • We rely very heavily on Asana as our task manager and location for task documentation. This means all of the information is in one place, and our VA always knows exactly what needs to be done next.


The Moral of the Story:

I personally think having a successful part or full time VA relationship actually takes a LOT of additional preparation work and diligence than people think. But in the long term it is absolutely worth the investment – after a month of heavy training, she was up and running and we were finally able to focus on building things that we could charge money for, instead of barely keeping up with weekly posts!

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