Virtual Assistant Business Owners

15 Entrepreneurs and Business Owners Share Their Virtual Assistants Tips

Want to know the Best VA Experiences and What Made It Successful?

Catch it from Business Owners and Entrepreneurs themselves!

 In this expert roundup, 15 business owners and entrepreneurs share their Best VA Experiences and what they did for it to be a SUCCESS!

Virtual Assistant services are very much in demand these days because they offer entrepreneurs and businesses owners huge benefits and, similarly so, offer a variety of flexibility to the virtual assistants themselves. 

A virtual assistantas defined according to Investopedia, is an independent contractor who provides administrative services to clients while operating outside of the client’s office. A virtual assistant typically works remotely from a home office but can access the necessary planning documents, such as shared calendars. People employed as virtual assistants usually have several years of secretarial or office management experience.

Virtual Assistants: Background 

The Virtual Assistant Business Owners industry has been around since the mid-90s. By the looks of it, it cannot be denied that it is a growing industry, and, as technology changes and progress, so does the virtual assistance industry to keep up with the current demand. As of this writing, there are thousands of VAs globally. 

To enlighten you further as to whether or not now is the best time to hire a Virtual Assistant, we reached out to 15 Business Owners and Entrepreneurs who have Virtual Assistants in their businesses and asked them the question: 

Tell Us About Your Best VA (Virtual Assistant) Experience

In addition, business owners and entrepreneurs were also required to answer the question: 

What Did You Do That You Felt Help It To Be A Success?

Virtual Assistant Business Owners Maddy

Maddy Osman

My best VA experiences resulted from a good hiring and onboarding process.

I write detailed job descriptions, narrow down candidates based on perceived fit, take the top candidates through a detailed interview process, and see if they can follow my directions during a paid test project.

Once they’re on my team, they go through an onboarding process that answers all their questions about working conditions around using certain tools and how to submit invoices. I share resources regarding specific client needs and how to use tools or deliver certain types of projects on an intranet that they can access whenever they need to.

Virtual Assistant Business Owners James

James Reynolds
SEO Sherpa

My company SEO Sherpa is a distributed organization. We have a head office in Dubai, but most roles are free to work remotely. At the time of writing this around two-thirds of our team are full-time remote workers. We have more than 40 team members in 8 countries around the world; USA, Canada, UK, South Africa, UAE, Thailand, Philippines, and Lebanon.

It’s fair to say I’ve learned a thing about operating a virtual team over the years.

If I were to boil that experience down to two key takeaways, it would be these:

1. Hire people who have a track record of excellence and love for the craft. It’s way harder nurturing talent when they are remote versus in person. That’s why I recommend you to recruit experienced “pros” who jive with your culture. Thankfully, you have the whole world from which to choose.

2. Visit your remote workers or have them visit you. Meeting your team face-to-face will do wonders for productivity and morale. We bring our whole team together once per year.

Virtual Assistant Business Owners John

John Rampton

My best VA experience has been an assistant I’ve had for the past four years who continues to be reliable, trustworthy, and productive.

They are my go-to person for all types of tasks because they make themselves available via multiple channels and know-how to prioritize what I need to be done. My VA is a good communicator and has a strong work ethic, which means I don’t have to micro-manage them or worry if they are actually getting the work done when I can’t see them.

I found my VA through a referral from a colleague, which I highly recommend to anyone searching for someone they can trust. Knowing that someone else had worked with my VA previously and knew their work was a good way to start the relationship off on the right foot. It’s also been successful because I make myself available when necessary so my VA can keep work moving. Also, having numerous tech tools in place automates some of their work so I can give them other tasks to do.

Virtual Assistant Business Owners Catherine

Catherine vanVonno


 For me.. my best VA experience is when my VAs show me that they can manage themselves.

This happens when they can complete job responsibilities on their own and require less management from me. They know what needs to be done and they make sure it happens.

When this happens, it’s because I allowed room for trial and error. It all starts with hiring people who know what they’re doing, then communicating the company’s vision and guiding principles to them. I make sure to remove obstacles by setting clear expectations for what I want to have done and how. Then I give them space to breathe. It can be hard not to micromanage, but I try to just get out of their way so they can work to their full potential.

Finally, I reward for ingenuity and critical thinking.

Virtual Assistant Business Owners Zak

Zak Mustapha

When I first got a VA I would look at how well they follow instructions and how much they charge per hour. However, it’s deeper than that. You need to get to know theirs why. Why they do this VA stuff in the first place. Are they out of a job and need to make a living? Is it something they enjoy? You don’t want someone who’s just doing it temporarily. Ideally, you want someone who’s passionate about assisting business people (or whatever you do). Because if they don’t then you may message them one day and not hear back from them for days (which has happened to me).

Setting expectations in advance and qualify them really hard so you can work with them easily. Always start with a paid trial period. And make sure you mention it’s “paid”. Give them tasks to do, show them how to do it (if needed) and set goals for each tasks so they don’t just do them robotically… because in the end of the day it’s all about results they can achieve and the time they can save you. You don’t want someone who’s just there to clock their hours and send you an invoice by the end of the week.

Virtual Assistant Business Owners Barbara

Barbara Weltman

 Big Ideas For Small Business

I’ve worked with the same VA for the past 12 years and the experience has been suburb.

Initially I had only a vague idea of how to use the VA’s services in my business. Over time, she took on more and more responsibilities, becoming an essential asset to the business. She not only completes all the tasks necessary, but is proactive in looking out for the business and suggesting ways to improve.

One of the ways that my VA and I work together successfully is continual communication via email. Even though we’re in different time zones, our ability to communicate regularly (and even at odd times—nights and weekends) has been critical.

Virtual Assistant Business Owners Elaine

Elaine Rau

I needed my spreadsheets to be organized. I had dozens of interns work on the sheets and they were a total mess. I needed everything to be in the same rows, color-coordinated, and same format.

I knew exactly what I needed when I needed it by and communicated the exact details of what I was looking for. When you’re clear with your instructions, you won’t ever have a bad experience with a VA!

Virtual Assistant Business Owners Kedma

Kedma Ough

Currently, I have a VA that has been with me for 5 years, and I have never met him. He changed my life and business and gave me back my freedom. I supported him as he supported me.

Virtual Assistant Business Owners Laura

Laura Yang Renner


I’m a big fan of systems. My best VA experience was when I had a system that I was able to transfer to her to take on. She stepped in without a hitch and made it her own.

Taking me out of the picture made it a success. I got out of her way. It basically became that she would tell me what she needed me to do to get the process completed!

Virtual Assistant Business Owners Melissa

Melissa Smith
Association of VAs

My best VA experience is matching clients with the right virtual assistant. Creating a win-win situation for the two individuals who had so much to offer one another in business. Jackpot!

Uncovering the communication strategy and ideal client fit are the keys to success. Finding the right VA that a client can communicate with easily and seamlessly is the first ingredient. Knowing the ideal client the VA started their business to serve in the first place is the other ingredient. Once I have these two pieces in place, success is inevitable.

Virtual Assistant Business Owners - John

John Mac

 The MotionEffect

I knew for a long time that I needed an editor on my virtual team. My best VA experience was by asking the right questions, being personal, and checking to see which personal values that also connected what mine and my business, I found a VA that really understands my message to the world.

Before hiring, I ask a lot of questions. Not only about the work to be done but testing their mindset around workflow, figure-things-out mentality, and what they think about the productivity workflows. I also test their overall ability to stay organized in both communication and productivity. Then I go hot on personal questions with the purpose of getting to know them. See how they handle a human connection and to be open and honest. In the end, I’m letting them know that I’m not going to work with an invisible VA that is afraid to show their face. I expect video calls to be the main method of communication besides Slack chats.

By being personal and direct from the start you’ll find out if the VA can handle a personal work relationship with good, open communication. And by making sure you find a VA that shares some of the worldview and personal values, they will be more invested in the mission and purpose of your business. Get personal but professional. And share the same values. A VA that is emotionally invested in your business will feel more connected and do a better job.

Virtual Assistant Business Owners Ray

Ray Blakney

Infinite Upcycle

My best VA experience was when I was just starting out over 12 years ago. Like many others at the time, I had just read Tim Ferris’s book The 4-hour work week and got introduced to the concept.

At the time, I was running a chain of brick-and-mortar language schools in Mexico, and as the only native English speaker on staff, I was the one who had to answer all the English emails. The business was growing, so at this point, I was spending 6-8 hours a day just on this task.

It was not as easy to find VAs back then, but after a few month search and some family contact in the Philippines, I was able to find somebody who was willing to work US hours for a great price.

Within 2 weeks, I went from 6-8 hours of emails a day to just 1 hour of emails. The VA I hired first was not that great – due to my lack of experience – but the change was enough to open up a new world. I let the first VA go within 6 months, but had hired another great one within a week after that. Now, almost a decade later, I have worked with dozens of VAs from Asia to Europe and it is the basis for me to build my businesses..

What helped me for it to be a success was embracing failure. By this, I mean that finding and working with a great VA required me to fail in my hiring dozens of times. When I started out, 2/3 of the people I hired did not work out. Now 3/4 have stayed with me for over 2 years.

The key was learning from why the ones that did not work (for me) did not work and then changing the hiring and training process to try to account for it.

At this point, my process, while not perfect, weeds out bad work and culture fit during the interview, which leads to more long-term success down the road.

Virtual Assistant Business Owners - Chaz

Chaz Edward
Web 2.0 Ranker

My best VA experience would have to be when I hired a virtual assistant from Indore who had four years of experience as a digital marketing generalist, who we were able to train and mold into a local recruiter for the Web 20 Ranker team. With a local recruiter we were able to set-up and register a foreign office, permanently staff the office, and tap into a wide range of graduates from the local universities.

Being able to elevate our team member and empower her personal growth and development has been my best VA experience.

We focused on hiring a generalist rather than a specialist and therefore were able to develop her skillset in ways that were directly beneficial to our business and that followed our processes and systems without any preconceived ideas that might be counter to our management and operation style.

Virtual Assistant Business Owners Rob

Rob te Braake
ABEL Finance

My VA is running my Linkedin. Simply put, she brings in leads and builds our brand without me lifting a finger.

The recurring best experience is when I open the Sheets and go through the leads and see her responding with messages that are on par with or better than I would respond, in my tone of voice.

She takes so much time of my hands, with very limited management time needed!

I spent a lot of time on the recruitment process, including paid test projects and multiple interviews, focused on skills and especially personality & mindset.

Once she was on board, I invested quite some time to train her on what we do and how we communicate.

Virtual Assistant Business Owners Vin

Vin D’Eletto

Word Agents

The best VA experience I’ve had was when we hired an independently contracted writer for a single project. She ended up joining our team as a full-time writer. Now, she’s been promoted to management and is a core part of our leadership team.

It greatly helped me when I started making clear expectations and having a great personality. When we hire VAs, we always make sure to provide them with clear direction and transparent expectations. In order to do this, we ensure that we have an iron-clad operations document ready to go for the VA when they’re hired. We use this document internally for a few “test projects” before making a VA hire to ensure there is no confusion in our directions/expectations. Our new hires often point out that this is very helpful and makes their lives easier. In this case, the VA we had our best experience with has a fantastic personality and great attention to detail. She is always proactive when onboarding a new project to ensure she has all the info she needs. If something pops up during production, she’s the first to reach out to run the issue down. 

The best part is that she does all of this with a smile on her face. While she may not have years of experience or formal training, her personality has propelled her into the position she’s in right now. 

Learn more about one virtual assistant business owners’ company that has won awards globally, Aristo Sourcing, by visiting About Us page. 


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