(Read the long version of this story here!)
The First Step is Realizing you Have a Problem
In 2011, my husband and I teamed up to create a website to help bartenders & cocktail enthusiasts learn advanced cocktail techniques. As our business grew, our evenings and weekends disappeared. We stopped seeing our friends and family as often. We felt guilty about going out to dinner or spending quality time together. It was unhealthy.
In late 2012, I set out to get help. I’d read the 4 Hour Workweek, darnit, and it looked easy!
Third Time’s the Charm
Our first attempt to hire a VA failed miserably. We hired an agency thinking it’d be easy to keep someone busy 10 hours a week. Instead, I spend about 20 hours a week trying to find things for her to do, while still doing all of my own work because “It’s easier to do it myself than train her.” We cancelled the contract after only a month.
The second time, I prepared by creating extremely long documents outlining elaborate processes. I hired a VA from Odesk, and she really tried hard – but my documentation was too long and confusing, and didn’t break the work into small pieces that were actionable. Worse, it wasn’t clear what was do be done when. We struggled along for 3-4 months before giving up.
In the fall of 2014, I decided to give this “outsourcing” thing one last try. I found a headhunting service that people raved about – but it was expensive. So if I was going to give this “outsourcing” thing one more try, I had to get it right.
This time, I prepared differently:
- I chose a task manager for our business (Asana) and documented all of the things our business does, who does them, and when.
- I carefully tested every process and documented every single step within Asana itself. Where helpful, I created Screenflow videos and linked to them within the Asana tasks.
- I created a gradual onboarding strategy that would mean I spent an hour a day meeting with my new VA. 15 minutes going over yesterday’s work and 45 minutes teaching her more tasks.
- I made a long list of simple but time-consuming one-time tasks that’d give her something to do while learning the recurring, ongoing work
When I felt ready, I headed over to Virtual Staff Finder and signed up. It took about 5 weeks to get through the process, and at the end of it we’d hired a highly qualified VA. This time was different. This time it really worked. Our VA has been with us more than 18 months. We exchange Christmas cards. She sends pictures of her kids. We’re truly a team.
Better yet? Chris & I got our lives back. We’re running the business now on just one day a week. How cool is that?
I learned how to delegate the hard way – through trial and error! Over time I learned the best practices of task management and delegation. 
