On Hiring and Working with a Virtual Assitant

Back when I made no money I used to like to “fix” things around the house.

We’re not talking DIY forum-guided fixing. We’re talking pure personal ingenuity.

One time I had to fix a hole in the wall the size of a watermelon. Unrelated.

I didn’t know the finer points of hole patching at the time but I knew if I had some plaster and a putty knife all I’d need was a surface to apply the plaster to.

Well I did have a beer case… Problem solved!

But how could I get the beer case to stay?

The eventual solution involved jerry-rigging a beer case to our oven with a rope. Younger me was a genius.

Fast forward many years and multiple children later and I don’t do as much fixing around the house anymore.


There inevitably comes a point when you realize you can’t do it all. Or at least not well.

What are the options?

There are a variety of ways that you can try to find the balance between work and life but one place to start is by hiring help.

You mean like a nanny?

Well, that might be an option but within the business, the first obvious place for me to start was to hire a VA – a Virtual Assistant.

Oh, so like a business nanny.

Let’s move on.

Skill-wise I identify as a software developer. But as a consultant, that meant I was also responsible for billing, bookkeeping, correspondence… the list seemed to go on and on.

And led into some areas that were NOT my expertise.

Increased anxiety, caffeine intake, nervous tics and the ever-increasing sound of billable hours swishing by …

Could I learn to do it all?

Of course! I’m a smart guy.

Did I want to?


Did I have enough time in the day to do it all?

Double nope. Especially on Daddy-Duty days.

As Rob and Sherry Walling, co-hosts of the Zenfounder podcast, point out, there isn’t just a work/life balance that happens when you’re running your own business, but a time/money one, too.

There comes a point when it is worth more to pay someone else to do it.

“Even if it doesn’t feel like there’s a lot of money in the budget,” Sherry observed on their debut podcast, “sometimes a housecleaner is cheaper than therapy. And therapy is always cheaper than divorce.”

(We all know it’s too true to be a joke, don’t we?)

There are some “outside” tasks that can help free your time, like housekeeping, yard maintenance or a grocery delivery service, but inside the business, a Virtual Assistant can be a sanity saver.

A Virtual Assistant is an independent professional who works remotely for a business on a contract basis.

In essence, they are a freelancer, like you. Just with different skill sets.

Possible tasks that a VA can take off your desk:

Feel the weight lifting already?

Just to be sure I don’t make it sound like you’ll get every day at the beach, a VA becomes part of your team and as such, you want to be sure that you’ll work well together.

I’ve worked with several different VAs over the years, and know that there have been times that I have not expressed my expectations clearly or implicitly enough, or delegated enough work.

Because of that, one of the traits that I appreciate, even at the first contact, is initiative. If they are a step ahead of me (e.g. confirming the appointment time the day before or breaking a larger task into smaller ones), I’ve learned that I ultimately win.

Told you I was a smart guy.

Keep in mind, you might need to experiment to find the right “fit” too.

So here’s a few tips for hiring, and working with, a VA:

Know the tasks you plan to delegate

The more specifically you can identify the work you want your VA to do, the better the odds of finding the person with the right skill set.

It’s usually smart to start with smaller tasks and then expand their responsibilities as you learn their competencies and their reliability.

Find the right tools to help you communicate and track progress

How can you best facilitate your work flow? There are numerous team tools available so try some options. Do you use screen-capture tracking? Trello boards? Planning Center? Google Docs? Skype? DropBox?

Remember, the goal is more productive work for you both.

Know your budget

Maybe you can’t afford a VA fifteen hours a week but you can start with five. Start there. You’ll probably find that as you can focus more on your area of expertise, your budget starts to improve too.

Know their availability as you set your goals

It’s no good offering same-day callbacks to your clients if your VA is only available three days a week. Discuss turnaround time and response time when setting the schedule.

Look around for other jobs they can take off your plate

Once you’ve found a VA that works well in your routine and that has proven trustworthy, you’ll find you start seeing other tasks they can manage.

Freeing you up for more billable hours or family hours or whatever sits at the top of your priority list.

Have a hole to plaster? I know a guy…