Ready to hire a Virtual Assistant? Two rockstar business women share their best tips

Source: Secrets of a Side Hustler

When you only have a small window of time to work on your business everyday, having help isn’t a luxury it’s often a necessity.

But when you’re used to being a team of one, adding another person to the mix can feel a bit intimidating. Maybe your inner thoughts even look a little like this:

“Where can I find right person?”

“Can I trust someone with my work?”

“What if it doesn’t work out?”

If you’re putting hiring on hold because you don’t know where to start (or even a bit scared to bring someone onboard) meet Jillian Adriana and Indigo Colton.

Meet our Virtual Assistant Mentors

After being hired by her friend and mentor Maya Elious to created a workbook and social media images, Jillian Adriana discovered a new and unique career as a Graphic Designer VA. After side hustling for a few months, Jillian is now a full-time entrepreneur who helps bloggers and online entrepreneurs take their visuals to the next level.


Indigo Colton, fell into the world of online business completely by accident in the summer of 2014. After her mom’s colleague needed someone to help her with social media, Indigo stepped up to help and discovered her passion in life: helping game-changing entrepreneurs take their biz to the next level.


Indigo and Jillian are rockstar business owners who understand what it takes to find the right help for your hustle. In this interview they share their expert tips that every side hustler should know before hiring help for their hustle.

What systems should business owners have in place before hiring someone?

One word: strategy. I work best with people who have a business strategy in place. My ideal clients are the ones who plan everything 2-3 months in advance. This makes my job easier because I know what to expect from them and can plan my time accordingly.

All business owners already have systems, even when it’s just them. I wouldn’t say they need to have any specific ones in place or perfected before bringing someone onto their team. The most important thing they can do with their systems is document them, though!

Because when you hire someone like a virtual assistant, they’ll need guidance and an introduction to your systems — however convoluted they are. Part of what hiring a VA will do is get someone who has fresh eyes on your systems so they can help you make them more streamlined and efficient.

So take the time to document your systems, whether that’s by recording walkthrough videos, writing the steps out in a Google Doc, or creating a list in something like Trello or Asana that you can easily share with them.


Ensure that you’re organized and have your systems documented before hiring someone for your team. Tools such as Asana and Google Drive can help you document your plans and screen sharing tools such as Screencastify, Camtasia and Screenflow can help you whip up quick tutorials.

What advice can you share to folks who are scared to relinquish control or delegate in their business?

Have a little faith! It’s hard to hand over such a substantial aspect of your business to someone else, so I recommend shopping around before making a commitment. I always meet with prospective clients via Skype to have a bit of a discovery session. This gives both of us a chance to get to know each other on a more personal level. I also let my them choose to do an optional trial project so they can see how I’m able to work with their brand. If they’re happy with the result, they can hire me. Don’t hire someone who isn’t a good fit.

Trust your VA to do their job!!

This is honestly something that EVERY business owner struggles with — even I struggle with this, and people pay me to delegate from their own businesses.

But you have to trust that your VA will get things done. Take baby steps when it comes to delegating — start with one or two small tasks. Then gradually add more and more until you’ve delegated all of the things that drain your energy.


In order to go up you have to be willing to give up. To truly soar in your business you need to know how to lead and empower others to do what they do best. Invest time in finding the right person for the job but once you bring them on board trust their expertise.

After you onboard a team member what can both parties do to ensure a successful relationship?

It’s important to remember a VA isn’t an employee–they’re an independent contractor. A client may have certain systems in place that work for them and the rest of their team, but they have to follow my processes if they want to work with me.

Communication is always key. When in doubt, ask questions. Face to face conversations are always best, even if Skype is the only option for that to happen.

Both parties need to communicate! It’s your responsibility to make sure things are working out and your VA has what they need, but it’s also on your VA to ask for what they need and make sure you’re on the same page.

I highly recommend scheduling a check-in video call 2-3 weeks after you’ve started working together. This gives you enough time to start working together and to get used to each other, and to have come up with questions to ask to ensure smooth sailing going forward.

Communication is vital for a successful partnership. Set up a process to have regular touch points and outline expectations of your working relationship.


What mistakes have you noticed that business owners make when searching for a VA or bringing someone on board?

The biggest mistake I see is not having a solid plan of action that includes a well-thought-out timeline. For example, I can’t help someone launch a product or service in a month and do all of their content upgrades and social media graphics at the same time. Plan ahead, and pull me in early so I can accommodate what you need in a timeframe that works for you.

A LOT of business owners rush through the process. Now, I know that I have a course called “Hire Your VA in 1 Week” which is a quick timeline. But the people I see rushing through the process are rushing without a system or a process.

Here’s what I see over and over again: A business owner realizes they’re really overwhelmed. They decide they’ll look for a VA someday, but until then they’ll keep muscling on. They reach their breaking point, whatever that looks like for them. They post in a Facebook group that they need a VA RIGHT NOW and put a link up to their site.

That’s it.

They don’t make a plan, figure out what they actually need help with, what kind of VA they’re looking for, or go through a thorough interviewing process.

Because they’re rushing it means they’re wasting money by hiring someone quickly who hasn’t been thoroughly vetted and can be the wrong fit.

Another mistake I see business owners make is dumping all of their business admin tasks or whatever they want to delegate on their newly hired VA and then disappearing, expecting the VA to make magic happen by somehow knowing what to do.

This actually just results in the VA being overwhelmed and confused and the business owner feeling frustrated.

When you hire someone make sure that you explain things and you’re available to answer questions. Because your new VA asking questions doesn’t mean they can’t do their job — it just means they need more information (and they’re asking for it!) to actually do what they were hired to do.

Even if you’re feeling stressed, do not rush through the process of hiring a VA because having a plan is essential.

Identify what you need help with, ensure that you have documented systems in place, conduct a thorough interview process and be available to answer questions after they are on-board.

In what ways can having a VA or team member help a side hustler grow their business more effectively?

In so many ways! Where do I begin?! By delegating out tasks that you don’t particularly enjoy, or ones that you know you aren’t great at (even if you do happen to love them doing them), you get to focus on doing what you truly love and what makes you happy, which is likely the reason you started your business in the first place.
There’s a reason I hire an accountant to do my taxes, right? I can purchase TurboTax and do it all myself, but I know numbers aren’t my strong suit and I would hate doing the work. Plus, I know my accountant loves what she does, which means she’s going to do a great job. The same goes for all aspects of business.

No one expects you to be great at everything, so find help where it’s needed. Always think of it as an investment, not an expense. What I do only becomes an expense for my clients when their business isn’t thriving because of my quality of work.

A side hustler can probably benefit from a VA the most out of all the types of business owners! When you’re running a side business in addition to your main hustle you need to really take advantage of all the time you have. When you hire a VA to handle say administrative tasks or customer service or social media it frees your time up to focus on creation, marketing, etc.

Having a VA on your team as a side hustler will help you grow your business sustainably, quickly, and effectively. Because your investment in a VA is really an investment in your business. And just because you’re a side hustler that doesn’t mean you have to burn yourself out trying to do everything solo!

Wow! How awesome are Jillian and Indigo? This interview was packed with gems on how to make the experience of working with a Virtual Assistant a positive and profitable one.

To stay connected connected with these amazing #ladybosses and check out their amazing services and resources for creatives, bloggers and side hustlers visit and

If you’re feeling inspired to start delegating in your business, download our workbook below to help you get clear on what you can delegate.


Over to You

Did you enjoy this interview? Let us know how you’ll implement the tips from Jillian and Indigo or what advice you loved from them in the comments!

The post Ready to hire a Virtual Assistant? Two rockstar business women share their best tips appeared first on Secrets of a Side Hustler.

* Source: Secrets of a Side Hustler

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