What an awesome VA-entrepreneur relationship looks like

“Virtual assistant” is a job description — and a way of working together — that didn’t even exist 10 years ago. Having an “assistant” sounds so fancy, a lot of people assume that it’s something for way, way down the line, for when they have a six-figure business with thousands of customers.

Many entrepreneurs swear by their VA as a key for helping them grow their business. But, how’d they get there? There are next-to-no resources to help entrepreneurs navigate this brave new world that is working with a VA. Nobody talks about what a good entrepreneur-VA relationship should look like, or how you make it happen.

So we thought we’d demystify the hidden world of virtual assistants somewhat by taking a close-up look at how one incredibly successful entrepreneur-VA relationship works.

In the process, we’re busting three of the most common misconceptions entrepreneurs have about what a virtual assistant is — and the difference that a virtual assistant can make in your business.

Misconception #1: “A virtual assistant is just about ‘tasks on demand’”
Misconception #2: “I don’t have enough work to keep a virtual assistant busy”
Misconception #3: “I’d spend more time telling a VA what to do than just doing it myself”

Meet Géraldine and Jen

Comme une Française founder Géraldine Lepère and her virtual assistant, Jen Rodgers, were just settling into their working relationship in 2015 when disaster struck: the company that Jen worked for — the company that had connected her with Géraldine in the first place — suddenly went under.

“I woke up one morning and went to get to work, and I couldn’t log into my stuff,” Jen remembers. “They gave us zero warning.”

Later that day, after some well-earned freaking out (I mean, what would you do if you woke up one day and the company you worked for had just completely disappeared?), Jen and Géraldine got on a call.

“Géraldine said, ‘Let’s keep doing this independently,’” Jen remembers. “‘What was their tool doing that we can’t do by ourselves?’”

Géraldine, who I talked to separately from Jen, remembers it much the same way. “We said, ‘We’ll stick together,’” she says. “She knew everything about me.

We were already working very well. I didn’t care what company she was in. She didn’t believe that everybody would keep her, but all her best clients just said, ‘I don’t care who I’m paying. I want to work with you.’”

The fact that not just Géraldine but all of Jen’s clients were willing to follow her wherever she went is a testament to just how indispensable good virtual assistants can make themselves to the people they work with. Less than a year into her career as a virtual assistant, Jen had already made herself such an integral part of her clients’ businesses, they literally couldn’t imagine being without her.

Géraldine and Jen have been working together for three years now, since Comme une Française was bringing in just $50K in revenue per year. Géraldine and Jen live on different continents. They work in different time zones. Jen balances the work she does for Géraldine alongside work for four other clients.

But for Jen, and other kickass virtual assistants like her, that’s all in a day’s work. It’s literally the job.

“I am here in order to make your life easier. Period,” says Jen. “However I can do that, I’m going to let you know, because I want your life to be easier. I want you to have the free time to do the things that you love, and not get bogged down in the stuff that’s just not worth your time.”

Misconception #1: “A virtual assistant is just about ‘tasks on demand’”

Jen recognizes that not all entrepreneurs have been as lucky as Géraldine when it comes to entrepreneur-VA relationships.

“I hear from a lot of entrepreneurs who have had experiences with VAs that they couldn’t trust, or couldn’t rely on,” she says. “I hear things like, ‘Well, I had a virtual assistant, but they did this,’ or ‘They ghosted on me,’ or ‘They didn’t do what they said they were going to do,’ or ‘I was paying them for doing nothing.’”

Real talk, you guys? Those people who have had bad virtual assistant relationships … have probably been hiring the wrong kind of VA.

“I find that a lot of virtual assistants, they want to sit there, they want you to email them their tasks, and then that’s it,” Jen says.

For the record, this is not the kind of VA that Jen recommends entrepreneurs hire for their company. “How much can they really do for you or for your business if they don’t know you or your business?” she asks.

This is part of the reason that, even though it’s the term most people would identify her by, Jen isn’t even sure herself if “virtual assistant” is the best term to describe what she does for her clients.

“‘Business and lifestyle manager’ is what I call myself now,” she says. “I do a boutique type thing. When I’m your assistant, we are going to get to know each other personally.

You can absolutely trust me. We’re going to take the time to build that relationship up. When you work with me, you have personal support, you have business support. I want to be your number two that you know you can come to,” she says.

That’s definitely the relationship that Jen and Géraldine have built. “Jen is the one that I trust,” says Géraldine. “Well, I trust all my team with my life. But Jen is the one who has access to everything.

She knows more about me than most people. She has access to all my emails. She has my bank information. She knows everything, and I trust her to make good judgments.”

Want to build a business that enables you to live YOUR Rich Life? Get my FREE guide on finding your first profitable idea.

Misconception #2: “I don’t have enough work to keep a virtual assistant busy”

A big concern that can trip up entrepreneurs who are interested in the idea of hiring a VA is that they aren’t quite sure about what a VA can actually do for them.

The good news: part of a good VA’s skill set is helping you figure out the best ways to use their time and their specific skills.

But that’s not to say it will be a perfect, linear process. “It takes a lot of trial and error,” says Jen. “There have certainly been things that we were like, ‘Let’s try this.’ And then it didn’t work out.”

“When we started out, it was just Géraldine and I,” Jen remembers. “We were the only two people, and we handled everything manually. Nothing was automated. When somebody signed up for our class, I literally had to enter their name and their information into this giant spreadsheet.

And then I would do welcome calls, because we were still really, really tiny. I’d call new customers and be like, ‘Hey, you signed up for our course! We’re really excited! Are there any questions that you have?’”

Those kinds of tasks were exactly what Géraldine needed help with at the time. They were important — but not make-or-break-the-business important.

And with Jen holding down the fort on the spreadsheets and the welcome calls, Géraldine was free to focus on bigger-picture tasks, like course development and customer research, that were going to help the business grow.

And grow Comme une Française did. And as it grew, two things happened. Number one: Géraldine and Jen spotted opportunities to streamline and automate, freeing Jen up to tackle more and more task. And number two: the Comme une Française team grew as well, creating new needs — and new opportunities for Jen to get involved.

“My position kind of morphed away from virtual assistant more to like business and lifestyle management,” Jen says.

When it comes to the specific tasks that she handles for Géraldine today, Jen literally counts them off for me on her fingers.

“I’m the head of customer care. Any time a student has a problem, or they read an email and have a question, I answer that. I manage her business inbox for her. I reconcile bank statements, and stuff like that. We have a journal of expenses. I keep that up. We’re trying out a new affiliate program, and I’m working with another member of our team on that.”

With the growth of the Comme une Française team, Jen’s role has also evolved to include serving as a sort of team co-captain. “I am Géraldine’s second-in-command. If she’s gone on a trip or out of town, then I’m the go-to person,” says Jen.

On team Comme une Française, all team communication runs through the project management tool Basecamp. If the team has a question for Géraldine or they need her feedback on something, they send it her way through Basecamp. If she’s not available, or they know she’s busy, that’s when Jen steps in.

“We have an amazing team, so very rarely do I even have to remind anybody that something’s due. But if there’s ever a problem, they’re going to come to me if she’s not around. Or sometimes, even if she is around, just because we know, if we can handle it internally, we don’t want to bug her with it.”

To be clear, this policy of “don’t bug Géraldine” is one that Géraldine herself wholeheartedly endorses. “I’ve always said, ‘Do as much work behind my back as you can,’” she says.

The more that Jen and the rest of the Comme une Française team can handle without Géraldine having to get involved, the more it frees up her time to think about big-picture planning and growth — in other words, the things that a founder should be thinking about.

Misconception #3: “I’d spend more time telling a VA what to do than just doing it myself”

A final misconception that people tend to have about VAs: that they’d spend so much time telling a VA what to do, that from a time-saving perspective they might as well not hire one in the first place.

But a good VA isn’t an automaton that needs micromanaging at every turn. They’re ready to spring into action — before you even have to ask.

As Géraldine’s VA, Jen makes it her business to ensure that Géraldine is making the absolute best use of her time that she can. From time to time, that means speaking up and letting Géraldine know when she sees that not happening.

One recent example: the dreaded email inbox. [Cue doom-and-gloom music here.]

“Géraldine was getting bogged down with the emails. She has a million important things to do, and sitting and going through a bunch of random emails is not one of those.”

So Jen did what a good VA does best: she asserted herself, and let Géraldine know, I can fix this for you. “One day I said, ‘Look. We don’t need you acting as a middleman.

I can go in and go through, I can mark all the emails that you need to respond to, and then everything else, I can respond on your behalf.’ That was something that I already did with several of my clients. So it just really easily translated over to her. It wasn’t a big deal at all.”

It can be a weird thing at first, as an entrepreneur, to be told by your assistant, “Go away. I don’t need you.” But again, this is the dream.

This is what Géraldine hired Jen to do: to take things off her plate and allow her to focus on the big-picture, strategic projects that are going to move Comme une Française forward — instead of whether the emails in her inbox are getting answered or not.

Jen gets how scary it can be to hand pieces of your business off to new people, because it’s something she’s experiencing for herself. As her relationships with her clients continue to develop, and the work she does for them grows more complex, Jen is actually in the process of building a team of her own.

Wish you could connect with more amazing people, and not feel awkward in social situations? Download our FREE Ultimate Guide To Social Skills below.

Along with the guide, I'll also send you my Insiders newsletter where I share other exclusive content that's not on the blog.

“I’m a major control freak when it comes to my clients. I’ve spent years building up these expectations with them, this level of trust, this relationship. And now to like be like, ‘Okay, other person, come into my business, and you take care of some of this stuff’ — I struggle with that myself.”

The fact that Jen gets how scary trusting someone else with pieces of your business makes her even more valuable to the entrepreneurs she works with. “You understand that tension of loving your work, taking pride in your work, but at the same time needing to let go — which your clients probably have a hard time with themselves.”

How to find yourself a Jen

If by this point in the post you’re Googling Jen’s name, trying to figure out how you can get her on your team, I don’t blame you. Unfortunately, Jen doesn’t have the bandwidth to take on the entire GrowthLab community — even with her growing team.

That said, Jen has seen the good, the bad, and the ugly when it comes to entrepreneur-VA relationships — both firsthand and through the experiences of other VAs that she keeps in touch with. And she has some no-BS advice for entrepreneurs about how they should go about finding and vetting a potential VA.

1. Spend time getting to know each other

“Have a conference call with this person. Have several calls with them. Get a really good feel for who they are. Ask them what they’ve done for other clients, see how you feel.”

Some questions to get the conversation started:

  • What are some of the tasks you’ve done for clients in the past that you’ve really enjoyed doing?
  • Tell me about a tricky situation that came up with a client in the past. How did you solve it?
  • Tell me about a time when you had to figure out how to do something that you had no idea how to do.
  • What are your favorite strategies for multitasking? Any productivity tools that you particularly love?

A rockstar VA will have a field day with questions like these. If a candidate doesn’t have clear answers, or talking about productivity doesn’t seem to fire them up or get them excited — that could be a red flag that the role is not a good fit.

“That gut feeling will tell you so much about somebody,” says Jen. “When you talk to somebody, you know immediately if you’re going to be able to work with them or not. If you talk to somebody and you have a feeling that you cannot work with them, trust that feeling. If you think it’s going to be a problem, it’s probably going to be a problem.”

2. Make a list of your tasks

“Take some time to really discuss the expectations that you have of them, what you need them to do for your business, and see if that’s in line with what they’re willing to provide you,” says Jen.

“What I see a lot of times is that the client expects something, and never fully communicates with the person that they’re hiring, and then the VA goes in with a different idea of what they’re going to be able to do for this company.”

A useful exercise to help you gain some clarity around this: before you talk to a VA candidate, make a list of all of the tasks that you deal with in a typical week.

Once you have the list, look it over, and get super honest with yourself task by task: Is this something that absolutely has to be done BY ME? Or is it something that, with some coaching and guidance, someone else could handle just as well?

Those second category tasks — those are the ideal jumping-off point for a conversation with a potential VA about what they think they can tackle.

3. Ask for testimonials

“If you’re looking at a virtual assistant, and they don’t have at least a couple of clients who are willing to say, ‘They’re amazing. This is what they did for me, I love having them as part of my team,’ then I wouldn’t recommend them. Do you really want to bring somebody into your business when their past clients can’t say good things about them?”

4. Trust your gut

“I had been a virtual assistant for less than a year when [the company I worked for] went under. I had no experience before that. But my clients had faith in me.

They gave me a chance to do it without a company backing me up, and it’s worked out really well. I’m super entrenched in all of their businesses. I’m an integral part. If you have a good gut feeling about somebody, rock it and see what they can do.”

Written by

Host of Netflix's "How to Get Rich", NYT Bestselling Author & host of the hit I Will Teach You To Be Rich Podcast. For over 20 years, Ramit has been sharing proven strategies to help people like you take control of their money and live a Rich Life.