On Hiring a Virtual Assistant (Something I Should Have Done Years Ago)

Tracy Osborn
7 min readJan 9, 2017

For the past seven years, I’ve been working on WeddingLovely, a wedding vendor marketplace and planning guide. WeddingLovely brings in revenue, but not enough to pay myself (or anyone else in North America) full-time, but enough revenue to be significant.

For quite a few years of working on this business (a true labor of love), I answered all emails, posted all blog posts on our popular weddings blog (which run one to three times daily), manually approved all small-businesses that joined our directories, not to mention that I’m also the designer and developer for all eleven separate WeddingLovely properties.

I did everything myself because I love what I built, but also because I couldn’t hire someone to do it for me full-time. I thought this was what I had to do.

I had heard about virtual assistants from sources like the Four Hour Work Week book, but the days of easy-to-work-with-and-cheap virtual assistants seemed to be over. Companies like Zirtual start at $398 for just 12 hours per month, when I really needed something like 12 hours per week. When my business is so low income that I struggle to pay myself, there is no way I can pay $400 for three hours a week.

Most “we’ll help you find a virtual assistant” services also all seemed to start at $50/hour at minimum. Of course, since I needed someone to write emails on my behalf, I needed fluency in English, so I mistakenly thought that I would require a virtual assistant located in North America who would charge rates I couldn’t afford.

Last but not least, there are a lot of services that, for a fee, would help you find a Philippines-based assistant. I worried about paying fees to a middleman (most seem to be around $500), being cut out from the process, and being “matched” with someone who didn’t work out.

Cutting to the end of the story: Today I work with a truly amazing woman in the Philippines. She works for me full-time for a price that I can afford and does great work. After so many failed starts, how did I finally successfully find a virtual assistant?

Here’s the process that worked for me:

Start documenting everything in detail.

First, I started documenting the tasks I’d like to outsource and these documents proved invaluable in hiring a new assistant.

I used Google Drive and Google Docs to write and hold all documentation and walkthroughs for my tasks:

For my sanity, tasks are also grouped in folders.

Each of these documents goes into detail in bullet points the exact processes that the task requires:

I find bullets easier for instructions (rather than paragraphs), and I try to add images wherever possible.

Note the video link! I started informally video-ing my processes and sticking them into a private YouTube account, and the combination of written and video walkthroughs has made on-boarding more efficient with less confusion.

Last but not least, all of these tasks are added to one main document showing what I need done daily, weekly, monthly, and as needed, with links to the specific task pages. I added to this list tasks that haven’t been started yet (highlighted in yellow) so my assistant won’t be caught off-guard when more tasks get added to her plate.

The process of writing the above sheet, breaking down everything I needed done into daily/monthly/weekly/as-needed tasks, and then building the individual documentation and walkthrough pages, helped me get my head around exactly what I needed done and made the process of hiring and working with someone 1000% times easier.

Skip the recruiters and middlemen — try forums.

I eventually stumbled on the website OnlineJobs.ph and was swayed that I could post a job advertisement without paying — you pay only when you want to view applicants.

I wrote up a job ad, posted, and waited… and didn’t wait too long, as after two hours I had 80 responses.

I was overwhelmed already, so I turned off the ad, paid OnlineJob’s $49 fee, and started going through applications.

Create a test (and pay your test-takers for their time)

Since I had already created my list of tasks, it was easy to pull out a few small ones and create a test from them. I built some sample businesses and a sample blog post that would need to be posted on social media, then passed them on to about ten of my top applicants with the documentation I had already created. I asked the applicants to send me what they would respond with, as well as track the time it took them to determine the correct responses. I took both quality as well as speed into account when “scoring” the responses I received.

I also made it clear I needed the time spent working on my test so I could pay them for their time, which I did at a flat $12/hour, higher than all of their posted hourly rates. I wanted to incentivize the applicants to give me their actual time spent on my test, and also because spec work sucks. Most took about 30 mins on my test, so paying folks for their time really didn’t cost me much.

Figure out what is really important to you.

WeddingLovely’s brand is deliberately down-to-earth, informal, and a little bit goofy. It’s rare that I send an email to a business without using an exclamation mark, smilie, or emoji. Surrounded by formal, uptight wedding businesses, I’ve deliberately made WeddingLovely a breath of fresh air.

In my responses, I received so many applications with applicants with very, very, very low rates — which was tempting—but their applications didn’t “feel” on-brand to me.

One applicant sent me a message, and I responded using my usual informal manner, using :) and !’s. Her response to me copied my manner, a different style than her original message.


She had a rate I could afford, great work on my test, and most importantly, she was aware of language styles and was able to pick up on my style without me asking for it. This was the person I wanted to hire.

Start part-time.

We started with part-time hours, paying through PayPal monthly. I started her on the tasks we did the test on during the application process, and I slowly introduced new tasks as things settled down and we established a process.

After a few months it was clear we worked well together, and we moved her to a full-time schedule.

Starting slow made it less chaotic on-boarding her, and allowed me to feel more comfortable letting go of all the pieces of the business I used to run. Worse case, I could have discovered that things weren’t working out and run another ad for a new assistant, and now that I had my process down and my documentation written, that prospect was much less daunting than it was before.

I couldn’t imagine running WeddingLovely now without my virtual assistant.

I wish I hired her four years ago, rather than less-than-a-year ago, as not only has my time freed up to allow me to do more design and development work, 2016 was WeddingLovely’s best year ever, crushing revenue goals. This is something I can only attribute to the small-businesses on WeddingLovely getting more attention than they did when I was doing everything, and therefore choosing voluntarily to move to a paid account without me spending time on any kind of sales process.

To review:

  • Hiring a virtual assistant is one of the best things I’ve done for my business and I wish I did it earlier.
  • Figure out what tasks could reasonably be outsourced.
  • Documenting everything is crucial for on-boarding (and is good practice anyways.)
  • Look at lesser-known sources like forums for finding virtual assistants.
  • Money shouldn’t be the top factor — try to determine a factor that is unique to your business and hire someone who fits.
  • Start slowly and don’t be afraid to try a new person if the first person hired doesn’t work out (since you have that documentation already written.)
  • It’s also pretty awesome being able to provide a livable wage to someone, even if they’re not in the same country as me.

If you’re looking for wedding planning and wedding vendor help, I highly recommend checking out WeddingLovely. I can also be found on Twitter and I’m happy to answer any followup questions there.

I hope this helps!

(This article also appears on my personal blog here.)



Tracy Osborn

Author of Hello Web Books. Traveling the world and climbing mountains.