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How To Hire Your First Virtual Assistant While Staying True To Your Business Vision

Wandering Aimfully Through Creative Business

How To Hire Your First Virtual Assistant While Staying True To Your Business Vision

If you're a solopreneur or independent creative, growing your team and potentially giving up some control can feel scary. Here's how I hired the right person for me with my first business, Made Vibrant.
Caroline ZookCaroline Zook Caroline ZookCaroline Zook

Written by

Caroline Zook

In 2015, I hired my first ever assistant, the wonderful and talented Laura. We worked together for three years, and I still consider hiring her one of the best decisions I ever made for my business. I want to share with you a bit about what the process of hiring was like for me, and how I managed to overcome the big fear I had that the magic and mission of what I’ve built might become diluted with the addition of a new person.

To kick things off, how did I know it was time to consider hiring?

The first two years of growing Made Vibrant was general such an enjoyable experience. I had the freedom and flexibility to experiment with different revenue models, and I had the luxury of teaching myself everything on my own time without having to worry about anyone else. For a while it felt like maybe I might always want things to remain that way, operating a business solo. Maximum simplicity, minimum responsibility to anyone else but myself.

That is until the end of 2015, when I looked up and realized running the day to day of the business was starting to make me feel a bit like one of those circus performers spinning plates on broomsticks.

Slowly I had been adding each new spinning plate—an Instagram challenge here, another new product there, a blog strategy, a creative practice, a Slack community. The list went on.

And all of those things were wonderful and helpful additions to my business, Made Vibrant. They brought me joy, they brought my business profit and they brought my audience value.

But I’d be lying if I said it wasn’t exhausting, what with all the constant running around and trying to keep all the plates from falling.

I was starting to feel a lot more reactive and a lot less creative.

That’s when I started considering the notion that an assistant might be the right way to go.

I remember the exact moment it dawned on me that something had to change. I was sitting at my computer literally just staring blankly at my calendar, almost on the verge of tears because the minutia of all the spinning plates I had in the air felt virtually paralyzing. I had no energy to even tackle my to-do list because the weight of the whole thing had me in a chokehold.

That’s when I asked myself these two simple questions: 1) Is my business making enough money that I can afford to pay someone part-time? and 2) Am I willing to let go of some aspects of my business in order to make room for more of what I value in my life (creativity, curiosity, ease)?

The answer to both questions was yes.

So what do you do once you’re ready to hire?

The first thing I did was ask my close business peers about their experience with virtual assistants/hiring just so I could get a baseline understanding of what I was getting myself into.

I’ll be honest though, while getting outside feedback helped warm me up to the idea that this could be a great and helpful thing, it also actually made the process feel a bit more overwhelming than it needed to be because I realized there is no uniform way that people go about hiring assistants.

Every business is different and every business owner is different, so it’s no surprise that there isn’t a one-size-fits-all solution.

But the more people I talked to, the more I realized I just needed to figure out what worked for me:

Once I realized it was my business and I could run it how I wanted to, the process felt less overwhelming because I realized I was free to just be myself.

Now, before we move on to the process of actually finding my assistant, let’s wade together through some of the big fears that came up for me once I decided to dive in.

My fears about hiring my first virtual assistant

1. Fear of the unknown.

Ahhh yes. That all-terrifying, unpredictable, sneaky little booger called The Unknown. As with all things that I’ve never done before, my assembly of what-ifs received their call to arms and started showing up in record numbers once I decided to finally hire someone.

As in all cases of the great fear of the unknown, I simply had to remind myself to, hello, breathe, but then also to accept that I don’t know what the future holds and that’s okay. I’m a big girl and I can trust myself to know that I’ll figure out whatever gets hurled at me.

Yes, all of those big scary things are what-ifs, but there’s also a great number of what-ifs that could mean wonderful things too:

Basically, my tip for silencing the fear of the unknown is simply to say, “Hey fear, yeah I know we’re flying blind here but I’m a pretty seasoned pilot by this point so just trust me, I got this. Now sit back and enjoy the flight.”

2. Fear of the collaborative process (as an introvert).

This is probably going to seem like a weird one, but I was literally afraid of being required to talk to another human on a regular basis.

Now, before you internalize how bizarre that sounds, just know that I am in fact an introvert. I enjoy the deep thought that comes with being alone, in my own head, and while I can definitely enjoy connecting with people under the right circumstances, sometimes interacting at all can leave me feeling a bit… drained.

So, I think a part of me was a bit apprehensive about the whole communication part of the process. Would it drain me to be in constant contact with someone? Would it leave me feeling overwhelmed?

Again, though, once I realized that it was my business and I could mold the relationship to reflect my introverted self, the fear subsided. (Also, I’ve found in recent weeks that if you’re just honest with people in telling them what you need and how you work best, they’re usually pretty cool with being accommodating.)

3. Fear of losing the magic.

Okay, so here’s the biggest fear of all. Somewhere in the back of my mind, I had to acknowledge:

I was afraid that getting bigger might mean losing some of the magic.

How arrogant is that?! The truth is, I’m not the magic. Maybe I’m an instrument of it, maybe I help the magic get out into the world, but it’s not me or even the business itself; the magic is in what the business stands for. It’s in the honesty of telling one’s story, the beauty of listening when inspiration calls, the connection that comes from supporting other soulful creatives worlds away from you.

And that means that someone else out there can be an instrument of all that too.

If the right person shares my same values and can get behind the mission of my business, then if anything, the magic of the business becomes stronger.

Which brings me to…

What to look for in hiring your first virtual assistant

Based on the fact that my biggest fear was diluting the core of Made Vibrant, the single most important thing that I was looking for in the assistant applications was a deep understanding and whole-hearted commitment to the mission of my business.

I mean it when I say: everything else was secondary to this priority.

Because even if someone was the most organized, most detail-oriented, most effective assistant ever, if what I’m doing doesn’t resonate with them in their bones, then I don’t think I would fully trust them to interact with the Made Vibrant community and pour that passion into whatever task they’re doing.

As an aside, my favorite and most unexpected part about hiring someone who believes in your mission? They can actually help ground you in your own WHY.

After simply interviewing Laura and chatting about Made Vibrant, she reminded me of the fact that among the various personal and professional development sites across the web, to her Made Vibrant stood out as a resource rooted in authenticity and relatability. When she said that, it actually served as a powerful reminder that I need to be doubling down on those things. It effectively helped me find my way back to the heart of why I started my own business.

Which is to say:

If you hire the right person, they have the ability to strengthen your core purpose, not to dilute it.

“If you hire the right person, they have the ability to strengthen your core purpose, not to dilute it.”

The process of hiring your first virtual assistant

Here are the simple steps I went through to find the right assistant for me.

1. Post the position listing your my blog and social media.

I went to my audience FIRST. If I’m going to find someone that is aligned my core mission, there is no group better qualified than my own audience. That’s why I started from the inside. I listed out the basic requirements of the position, what I was looking for and how to apply.

(Note: I included instructions to submit an email as an application rather than to simply fill out the form because I wanted to immediately be able to tell if people could follow instructions. You want to look for ways to further qualify your candidates so the actual process of submitting an application is one way to do that.)

Things you definitely want to include:

2. Go through applications and pull those that immediately stand out.

I made it a point to read and give my full attention to every email that came through. If the email followed instructions, the candidate had the skills/experience that I required and if the email was well-written with strong communication, I immediately whittled the stack down to those candidates.

From there, I went back through again and made note of those that felt particularly invested in Made Vibrant’s mission. I opened the door on this a bit when I asked applicants to include why they felt they were right for the position, but those that stood out to me were the ones that took that opportunity to communicate why their values were deeply aligned with those of the business.

3. Follow-up with additional questions.

Lastly, I knew that I wanted to narrow the field down to just a handful of applicants for live interviews. I simply didn’t have time to interview more than two or three candidates, so to get my list down to those few, I sent the top applicants some last final questions to dive a bit deeper. Some were skills-based, some were scenario-based to get a sense of how they’d respond to different situations, and others were simply to get an idea of how the relationship could grow in the future. Here are the exact questions I asked:

The answers to these types of specific questions actually made it fairly easy to identify three top candidates. Once they responded, we set up a time for a Skype interview the following day.

4. Set up Skype interviews with your final top candidates.

This step for me was more about finding the best personality fit. I knew going into it that I didn’t need to find a best friend, someone JUST like me, but I did want someone that I would enjoy communicating with on a regular basis and I wanted to make that personal connection before agreeing to set up the professional relationship.

This is when the choice became really clear for me. I think even in a virtual interview, you can get a sense of how you click with someone, where the conversation goes, how enthusiastic they are about working with you, etc.

My conversation with Laura flowed naturally and I got off the call feeling not only like she was the right fit, but I actually felt re-energized about my own business. I knew that was the kind of energy that was worth risking all the scary unknowns for!

5. Draw up a contract and get to work!

Once I contacted Laura to tell her she got the gig, we got to work right away! I sent over a contract with payment terms, “termination” terms (ie. what happens if either of you want to end the relationship, and the basis agreement that she’d be acting as a contractor rather than an employee.) **Note: I’m not a lawyer so if you are going to draw up a contract, I recommend at least consulting with a lawyer.

Then we set up a kick-off call to bring her up to speed on what was going on with Made Vibrant and I trained her on some tasks. As we moved along, we updated and evolved the tools/processes that we used to manage our workflow. In general, though, we used a combination of Slack, Google Docs, and Asana to manage tasks, which worked very well.

Growing a team can be unsettling if you’ve never done it before, but after three years I can say it was MORE than worth it to feel like I had someone on my team rooting me on and who was invested in seeing the Made Vibrant vision come to life.


How To Hire Your First Virtual Assistant While Staying True To Your Business Vision

(Big Fat Takeaway)

Yes, hiring an assistant requires you to give up some control and wade into uncertainty if you've always done things as a solo creative. But, it also allows you to do more things with less stress. Just make sure you take the time to find someone aligned with your business mission.


This article written by

Caroline Zook

She/Her | Artist, designer + writer passionate about helping soulful creatives grow into their brightest selves. Lover of bright colors + even brighter people! One half of the crazy duo running these parts!

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