5 Key Lessons I've Learned from Working With A Virtual Assistant

Update: July 1st, 2016

Because our business has grown and we have hired new employees in-house, we decided to stop working with Kaye. If I were to hire another virtual assistant in the future, here's what I would do differently: 

1. I would make sure whoever I hired did not have a coinciding job. I think it's important they focus all of their attention on being a VA.  

2. I would set specific hours from the beginning. Being in a different time zone can be difficult, and it's much easier to obtain the information you need from someone right next to you instead of thousands of miles away. They would need to have a set schedule so we know when we can ask questions, delegate work, and get updates. 

Virtual assistants can be life savers, but you have to research and make sure they are the best fit for you and your business. HDCo realized having everyone on the team in an office together is easier and more practical for the kind of work we do here in Columbia, MO. 

This summer we had some huge changes at Hoot. What's been one of our most successful? Hiring a virtual assistant.

What's a virtual assistant? You ask, And what do they do?

Well, that's exactly what I'm covering today: I'm going to break down what a virtual assistant (VA) does, how we went about hiring someone who operates 8,000 miles away, why we love having her on our team, and the top 5 lessons I've learned from partnering up.

Let's dive right in!

I've learned so much from hiring a virtual assistant this summer! Wondering what a VA does, and why you might consider hiring one? If you're a small business owner overwhelmed with trying to do it all yourself, you should really consider the benefit of hiring a virtual assistant to help you tackle it all. | Hoot Design Co.

• How did I learn about virtual assistants?

In June of this year (yes, during one of my podcast marathons) I came across Chris Ducker, the NYT best-selling author of Virtual Freedom and expert on virtual assistants.

Now, I'd heard the term "VA" before from a few podcasting entrepreneurs, but I really didn't know much about the concept. But after becoming a fan of Chris Ducker's podcast and downloading his book, I finally got the whole picture:

VA stands for Virtual Assistant – that is, an assistant who operates remotely, rather than on-site. It's a pretty self-explanatory title, really.

Virtual assistants are professional assistants that focus on tasks that can be completed online, and, often, according to their own schedules.

• So why hire a virtual assistant?

Hiring a virtual assistant could be a great choice for small business owners who feel like they're exhausted trying to "do everything themselves." You know: trying to be the CEO, and the COO, and the CTO, and the head of sales, the PR boss, media relations specialist, secretary, accountant, research head, development head, chief engineer, social media strategist... Gahh!

The truth is that running your own business requires a seriously HUGE amount of work. After years of trying to tackle every single aspect of business myself (and raise two kids and maintain a family at the same time!) I realized I was demanding too much of myself.

It was actually hurting my efficiency and my business to try and play every single position in the field while calling the plays and running the bases.

For me, this summer was the right time to reach out. ⛅️ 

And I found the perfect VA through Kaye.

Kaye has experience in all the areas of business we needed – including background in SEO (search engine optimization – making your website Google search-friendly) and graphic design background. And, Kaye's a mom too, so that connection was pretty instantaneous.

Her recommendations were fabulous, and since hiring her we've had a great experience.

In the months that have passed since June, I've learned a lot. And I want to share what I've learned so far from this experience with all of you!

Whether you're planning on hiring a VA, curious about what it's like, or just trying to figure out the next step for your biz, I hope this list can give you some insight.

So here it is!

5 Lessons I've Learned from Working with a Virtual Assistant

1. You've gotta get your *ish together

 So we definitely were Carol in this situation 😁

So we definitely were Carol in this situation 😁

One huge lesson we learned right away is that hiring an assistant who lives 8,000 miles away means you've gotta get your *ish in order.

Kaye lives in the Philippines (halfway across the world!) and operates 14 hours ahead of our time zone here in Columbia, Missouri. So if we don't have her tasks ready to go, she could be sitting on her bum waiting on us all day.

Not good! In order to achieve success working with Kaye, we've gotta get our end of the deal straightened out.

But how the heck are you supposed to do that as a small business?!

By setting up processes. Lots of processes. We've spent a lot of time this summer streamlining our workflow to ensure that the steps we need to take for accomplishing goals will be roughly the same each time. It's already been a huge boost for our efficiency to have an established workflow in place. 

Getting all the pieces in place is still something we have to work to stay on top of, but we're getting better every week. 

2. Communication is key 🔑

When we don't have good communication with Kaye, things fall through the cracks.

BUT when we give Kaye a detailed list of tasks, including links or examples alongside clear explanations, everything runs very smoothly

 This is me.

This is me.

There's far less room for error when operating in different time zones, thousands of miles apart. We can't look back over a desk, and say "Do you have those TPS reports Kaye?"

So what this really means is that communication as a manager is essential. I've really learned a lot up my communication game throughout this experience. I can't rush through instructions or try and half-ass my task list when someone will not be able to ask questions about what I meant!

One major game-changer that we discovered is the power of creating a library of screen-sharing tutorials using Screen Flow – basically, I can record exactly what I'm doing on my computer screen in tutorial videos that we can pass onto Kaye. (You can also use QuickTime to record your screen on a Mac, fyi!) 

I love how Screen Flow allows me to show Kaye how to do something with a quick video of my screen and my voice-over instructions. This seriously helps cut down on miscommunication – and of course Kaye can play it again and again. (No doubt her fave hobby 💁)

Creating a library of tutorials is SUCH a good investment in the future of our company. If we ever need to expand and train someone else to use our system, most of our training can be done via our videos. Think of what a major timesaver these are!

Video tutorials are a tool we hadn't ever used in training before, and we'd been seriously missing out before. They're extremely efficient, have low production costs, and can be used again and again. Total win.

3. use a staffing agency!

When hiring Kaye, I used Virtual Staff Finder to help us out with the process. It was a great move.

We paid them $450 to find three candidates based on a detailed job description and info about our company. They provided us with excellent candidates with detailed resumes, cover letters, photo IDs, personality test results and personal photos. I was also able to look all three candidates up on Facebook.

Out of the three candidates, I chose to interview two. They were both SUPER qualified, and had EXCELLENT English skills.

We asked them questions via email and I held 30-minute interviews with both via Google Hangout so that we could interact face-to-face. I had such a hard time deciding between the two candidates but decided to choose Kaye because we loved her design style and her experience with web design and production.

I would never have felt comfortable reaching out to someone via Elance or Upwork for an ongoing position that required long-term commitment. I also really appreciate the time and effort Virtual Finder made into finding the best candidates, and doing the up front work of vetting dozens of employees. This would have taken me HOURS, and I probably still wouldn't have felt 100% confident that I knew exactly what I was getting in an employee.

Virtual Staff Finder also gave us some great resources on how to pay your VA and notes on cultural differences between American and Philippine culture that have been super helpful.

I highly recommend VSF, and wouldn't go any other route if I were to do it again.

4. The world is tiny 🌏

This learning point is a plus! I have been amazed at how easy it is for us to communicate with Kaye. Here are some of the apps/technology we use to get the job done:

1. Google Hangout iPhone App

Google Hangout is great for when you're at your desktop, but what about when you're at home? Enter the Google Hangout iPhone app.

This app is phenomenal for communicating with Kaye when I'm not in the office, which is SUPER typical because she is 14 hours ahead of Missouri time! Luckily Kaye is quite the night owl (and I'm definitely a early bird), and I find working before 6am to be hugely productive. We often connect in the early morning hours my time, evening hours her time, about her daily work flow.

2. Google Drive

We share files constantly via Drive. We upgraded to 100GB storage with Google this year, and that's made the file sharing process absolutely seamless. Anything we need to share with Kaye we can drop into our Drive (we've got quite the folder system set up!) and it's one-and-done.

3. Adobe Creative Cloud

Adobe Creative Cloud is a subscription service from Adobe that lets you access all the Adobe Creative Suite software you need on multiple computers. That means Illustrator, Photoshop, Indesign (and more!) – all the programs we need to use daily – are all up-to-date for one subscription price. The fact that Kaye is 14 hours ahead of us means she is often working when we are not and vice versa, so we can leverage our subscription accounts more easily due to the time difference.

3. Email

Well, this one is a no brainer. We're able to get lots of basic communication accomplished every day using email. At the end of each workday, Kaye sends a status update letting us know these four things (taken from Virtual Freedom)

  • 1. What did you do today?
  • 2. Do you have any questions?
  • 3. Do you need anything from us?
  • 4. Do you have any suggestions?

Keeping a consistent format for these questions makes these emails straightforward and efficient!

5. The difficulties of working mothers are universal

<And we run the world.>

 That's right!

That's right!

One of the most interesting things that has struck me since working with Kaye is that we are all doing this for the same reason.

We want the freedom to set our own work schedule and be with our families when we need to be. That's why I work for myself, and that's why Kaye does too.

Whether you are in the middle of Missouri or the Tuna capital of the Philippines, we all want the same thing. That makes me super happy (#womenhelpingwomen 🙌) and sometimes when there is added effort in working with a VA, I remind myself that this type of freedom isn't easy.

Now meet Kaye!

 Kaye, Mark and Messi!

Kaye, Mark and Messi!


Mark Gabriel Estrella – Hubby
Messi Gabriel Estrella – 2 year old son (and super cute!)

Educational Background:

Bachelor of Arts, English Major in Literature and Linguistics

What attracted you to being a virtual assistant?

I hadn't thought of this career back in college. But then I worked in a call center company for a while, and one of my colleagues introduced me to a job based from home. When I looked into it more, I realized it’s a great opportunity to work from home and improve my skills at the same time.

I am always being challenged to learn something new, to believe in myself, and grow. Besides all that, it is so much fun when people ask “What do you do?” – I’ll answer that I’m a virtual assistant, and wait for their "...A what?!" before explaining what I'm working on. It happens all the time!

What attracted you to Hoot Design Co.?

I decided to apply for the job based on Kristen's description because the skill sets it required are familiar to me and I have a lot of related experience. But one difference is that the platform, or the backend site Hoot uses is different than what I'd used before and I wanted to learn it. Plus, I was a little curious of what the graphic design and branding or marketing business is all about. The exact kind of business is new to me!

What has been the most challenging thing about working for HDco?

Well, a lot actually! What’s challenged me most is learning how to use Illustrator and Photoshop. And I love it, coz as I said during my interview, I love learning new things that let me grow my skills and be useful for the team.

What has been the most surprising thing about working for HDco:

Aside from having an approachable boss and cool team, I’m surprised that all the tasks have been very easy if you’re really willing to learn. And they offer a very good service to their clients!

Describe your daily schedule:

Being a work-at-home mom, I love working while having the pleasure of taking good care of my family each day. Every day in the daytime I have the chance to cook for my family, cuddle my lil guy (he's 2 years old), give him a bath, put him to bed, then do some household chores, I also have some time to watch movies online then at around 5 in the afternoon it’s my time to work as a VA!

If you could name the one thing you are working for, what would it be:

The luxury of working at home in my own chosen time while watching my son grow. With this job, I can be an effective Virtual Assistant and a Mom at the same time.

Thanks so much, Kaye!

If you have any questions about what it's like to work with a virtual assistant, our process, or why we chose to hire a virtual assistant, please let me know! I'd love to talk with other small business owners about the steps you're taking to make your business a successful reality.

Love KGB.

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