How to Hire the Right VA Without Losing Your Mind: A Simple, Stress-Free Playbook

If you’ve ever thought “I need help—but what kind?” this episode will clear the fog. 

I sit down with Virtual Assistant veteran Rachael Davila (20+ years in the field) to unpack how to hire smarter, onboard better, and actually get your time  (and sanity) back.

In this episode you’ll learn:

• Why hiring fails more often from mindset than skill — and how to move from solopreneur to teampreneur.
• The difference between onboarding and offloading (and why onboarding wins every time).
• A practical roadmap: break goals → projects → tasks and use Do / Delegate / Delete / Delay to decide who should do what — plus how to match tasks to the right kind of support (doer, collaborator, specialist, or personal assistant).

By the end of this convo, you’ll feel equipped to create a handoff list, choose the right VA type, and trust the process on your way to building a stronger busines. 🎧

👥 ABOUT THE GUEST

About Rachael Davila:

Rachael Davila is a Virtual Assistant mentor, implementation strategist, author, and founder of Extra Hands! Virtual Assistance. She’s been a solo VA since 2005 and hired her first assistant in 2021, giving her a unique perspective on both sides of the VA/client relationship. Rachael knows how overwhelming it can feel to figure out virtual support, and she’s made it her mission to help business owners navigate the sometimes-scary but always-worth-it process of finding and working with the right VA. She’s the host of the Hey! Do I Need a VA? podcast and author of the book by the same name. 

🔗 LINKS & RESOURCES

• Connect with Rachael on LinkedIn
• Do you need a VA? Learn more about how Rachael can guide you find the perfect fit here!

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Transcript

Natasha (00:00)

Hello and welcome to the show, Rachel.

Rachael Davila (00:02)

Thank you. Thank you for having me, Natasha.

Natasha (00:05)

Yeah, I'm so excited to have you today. think talking about virtual assistance and help in your business is a passion topic for me because I know so many people struggle with it. But when done right, it can be such an amazing thing in your business and really help you scale. And one of the things I love about you is that you've been doing this for over 20 years. And I think a lot of people think of virtual assisting as rather new. So I love the perspective that you can bring. And I'd just love to check in with you just as we start this conversation.

How has this industry evolved and changed over the last 20 years?

Rachael Davila (00:39)

my gosh, so...

When I started, I did a virtual training program in 2004 at AssistU. And at that time, it was one of three training programs for virtual assistants. one year in, we celebrated their 10 year anniversary. So it actually had been around longer than I had known it. But when I first found out about it, I was like, what is this?

it's magic. was like everything I wanted to do and actually had been doing. Like when I think back to my career, I was a virtual assistant before I even knew what a virtual assistant was. And back then, nobody knew what a VA was. If I said I'm a VA, they'd be like, you work for the Veterans Administration. I was like, no, that's not, that's not what I do. And so there was a lot of education that I took clients through.

before they worked with me because I had to share what it was that I did, how I did it, and how it could benefit them.

I think over the last 20 years, now the pendulum has kind of shifted the other direction in that everyone knows the term, but it's used for AI chat bots on websites all the way up to executive level, you know, assistance. And so I think now it's kind of gone in that other direction where people are like, oh, you're a VA, but then they associate you with maybe a local.

cost overseas VA and that's not what I do either. So I'm back to educating clients on what it is that I do and everything.

Natasha (02:34)

Yeah.

And this isn't a specific question that we discussed beforehand, but maybe it would be helpful because as you said, there's such a broad spectrum of what virtual assisting can be applied to. What do you think is one of the most kind of basic approaches of defining that that we could use for today's call or chat?

Rachael Davila (02:52)

Yeah.

So the way I word virtual assistants are a business owner, because VAs are business owners, who works with other business owners to do their administrative operations and general admin tasks. And so sometimes that can be personal stuff. Sometimes that's business, or most of the time it's business stuff. But it's done virtually. So phone, email,

email, web-based technology, stuff like that. But we're not employees, we don't work for you, we work with you. And we are our own business and we provide the administrative support to other business owners.

Natasha (03:38)

Yeah. And I know one of the things too, when people start to approach finding a VA or even maybe hire, this might be the first hire for a lot of solopreneurs. Can you help us understand what are some of the biggest mindset shifts that an entrepreneur might need to make before bringing someone on board as a VA?

Rachael Davila (03:59)

So a couple years ago, I hired my own VA and learned how scary it is from the client side of the relationship because I am what I call a collaborator VA. And so I'm solution oriented. I want to take my clients through the whole process. And my VA was very much a doer VA, very much tell me what to do and I'll do it. And I had never stepped into that.

delegator realm that I mean, when I tried to delegate things to my kids and my husband, it never went very well. So was like, I'm not a good delegator. How can I, you know, handle a VA who needs that much kind of managing and what I went through in that first like year was letting go of my perfectionism, letting go

of, I can do this myself. Why do I gotta pay somebody to do this? And so I think for a lot of clients, they kind of come with, I know I need help, but how do I release the clutches to let somebody step in and help me? And can I receive that help? can I?

work through the discomfort of those first couple of months where we're getting to know each other to really say, that's not how I want it done, and then be able to take the time to explain the changes and everything to where.

the VA can then go, okay, I know what's going on now and I don't make the same mistakes again. So I think in terms of mindset shift, it's shifting from a solopreneur mind to a teampreneur mind. And it's also that letting go of the things that you don't need to hold onto anymore, but also,

letting that trust build, both sides kind of make mistakes in the beginning, but then having those conversations to say, okay, I don't want it done that way, let's do it this way, and then learning from that.

But I also think that there is a perspective of you don't have to stay in the relationship if it doesn't feel right or it doesn't last long term. Not every relationship is meant to last forever. And sometimes you will learn.

Even in the struggle with a VA, there is something to learn from it so that when you work with your next VA, can kind of go, that maybe wasn't the right fit, they didn't have the right tasks, or I needed them to do this before I could shift to a different task project that they weren't the right fit for, but a new VA is.

Natasha (07:01)

Yeah, I think that's important. And I know that back when I was working in corporate, I was at a position that had a lot of high turnover and it was really unsettling for me because obviously, and I think this is the right approach. We want to give every tool to the per like, we want to do everything in hiring to make sure that we get the right person and we want to give them all the training support to, you know, help support them. But ultimately not everyone is the right fit. And I had to really embrace the mindset of recognizing that and.

A lot of people hold on too long before making a switch. And if the relationship is in alignment, both parties are going to feel it. And so that mindset shift was important. So I'm glad that you bring that up because if you're doing this for the first time, it's likely that you'll make a mistake. And I think that's actually one of the most common things I see is people don't realize how difficult it is to get that right person if you don't have any experience in it.

Rachael Davila (07:54)

Yes. it to dating, right? Usually it's within the interview process, but...

You might have to kiss a lot of frogs. You might have to go through a number of VAs before you find your right fit. So it is looking at the qualities of the person too, not just who can do your task list.

Natasha (08:17)

Yeah. And how you think together, which is very much the dating world, right? How do we work together? Kind of along this line of, I have a few different questions kind of unpack some of the things that you've said. And one of those is just, ⁓ you talk about onboarding, not offloading. So can you explain what that means and why it's critical when you're bringing someone on?

Rachael Davila (08:39)

So in the process that I take clients through,

for the coaching side to prepare for a VA. We talk about the handoff list. We talk about what kind of VA they need. We talk about budget. But we talk about the qualities beyond the person, or beyond the task list, I mean, the qualities of the person, because a lot of business owners have gaps that they don't necessarily realize they need somebody to fill. And so part of that onboarding,

is having those conversations and gearing up to not just hand off the tasks, right? That would be offloading. ⁓ But onboarding is this is how I do it and this is why these things are important to my business. These are why I'm having you do it instead of me do it. And it's more of a conversation and a collaboration than just saying,

Here's the task, just go do it. ⁓ For me onboarding feels more relational than transactional.

Natasha (09:50)

Yeah. And at the end of the day, you know, the biggest part of our businesses is how we interact with the other people in it. And so making that relational and feel good, we're going to get those outcomes and we're all goal aligned. So I really love that approach. And everyone on this podcast will hear me say relational all the time. Mine's more towards relational marketing, but anything relational that we can do in business I'm all for. And one of the other things I heard you talking about was identifying your delegation style.

Rachael Davila (10:09)

Bye.

Natasha (10:20)

and how important that is to impacting your success with a VA. Can you impact that delegation style a little bit?

Rachael Davila (10:28)

So there are different delegation styles, right? Some people are like, here you go, do it and just send it to me to review, right? And others are like, I want to be kept in the loop. Keep me informed of what's going on. Others are like, hey, I need to verbally process this. Can you listen to me just talk and then tell me what I said and what we need to do with it. And so I think with

in the leadership and managing style, if you know that you are more hands-off,

That means you have to do more upfront with for a VA to come in, right? You have to have clear processes. You need to be able to share what you want in clear, concise terminology so that somebody could step in and just do the work. But if you are more of that like collaborative style or you want to interact more often, some VAs don't want to have that interaction.

and some VAs do and some clients don't and some clients do, right? And so it's knowing what you need. Because if you're a visionary and you can't break your vision down into small individual tasks, how are you going to hand stuff off? You might need a VA who is more collaborative, who can listen to what your goals and dreams and big vision is and go, okay, I see what we need to do. Here are the milestones.

here are the projects, here are the tasks, here's what you do, here's what I do, and they can help guide in that way.

But if you don't really know that that's what you need and you're just wanting to hand stuff off, but you're not in that style to have that clarity, then that's where lot of, communication breakdown happens. it's fit's not gonna be right because you're expecting a VA to handle things that they're not equipped to do.

Natasha (12:37)

Yeah, that was actually my next question was about how VAs can support the visionary brain, because if you're the CEO of your business, most people fall into that visionary category. And like you said, they have this big idea, but they don't know how to, you know, break down the little steps to get there. And that's why they need a VA. The other thing I see with visionaries is they need someone to filter and say, okay, here's the ones that actually matter. And sometimes they will drive their employees or VAs.

Rachael Davila (13:06)

you

Natasha (13:06)

crazy

with all these different, you know, paths. And so if you don't have someone who can go, hey, these are the priorities, or if you can't, you know, put that rev limiter on yourself, you can easily ⁓ end up going down all these paths. So yeah, I would just love to just kind of keep diving into this about how VA's can support that visionary role.

Rachael Davila (13:26)

sometimes...

visionaries need that big picture collaborator to create that workflow. Right? When I have a break a project down from big to small, from goal to small. And in there, talk about everyone has these big goals and they're like a boulder. So you got to break that boulder down into the milestones. Those action steps along the way that you're like,

It's not the finish line, but it feels like you're making progress towards your goal. And then from there, those are made up of projects. So how do you know you're getting to that milestone? You completed these projects. Now, a lot of people, think something like social media, right, is a single task, but really that's a project because projects are made up of lots of little tasks. And so...

for a visionary to not be able to go from my vision to break each of those steps down to the small task to then hand off to somebody, then they need somebody who can do that. And sometimes they need that person first in a strategist or a collaborative VA or an online business manager, somebody who can think that broadly and see, I know when I'm looking for an ideal client,

I want to, I want that vision. I want to know where we're going, why we're going there. What's the, what's the hope, the dreams, right? Like I want to be part of that. And so, so I really hone in on when they start to get off track, right? You start doing tasks, you get in the weeds, you're like heads down doing the things and then you look up and your client is like, yeah, that workshop that we just spent

two months building out no longer supports my vision and we're doing a completely different thing. Sometimes I say, are you sure? Maybe we can reword it. Maybe we can shift it. Maybe now's not the right time to launch it. But sometimes you need that.

business perspective, right? Like I'm a business owner. So when I'm talking to my clients who are business owners, I can say, you know, your goal was this and we've been building towards that.

Let's keep going because the other squirrels, the shiny objects that you're now looking at may not necessarily be a different path. They just might not be part of this milestone. It might be something further down the road. let's, capture it. Right. A friend gave me this beautiful imagery. She's like, ideas are like butterflies. They land on you. And if you don't capture them, then they fly away and they don't come back.

And so sometimes it's just saying, I see where that fits into the big picture. It's not right now, it's a later step. So let's capture it, put it someplace safe. So then when we get to that point, we can revisit and then start building that. And I feel like...

There are doer VAs who can do that. I mean, my VA in the Philippines, he's very much a doer. He does amazing graphic design and stuff. But when I told him that I was working on my book, he stepped in to say, okay, well, while you're doing that, I can do this. so it wasn't necessarily keeping me on track with my goals. It was showing me places where he could step

in and take things off my plate so that I could

focus on my stuff. And so I feel like VAs can really step in in a number of different ways for visionaries to hold their vision in alignment, to hold it up and say, are we still on track for this picture? Or to say, while you're off chasing that shiny object, I'm going to hold the fort down so that when your path comes back,

be able to meet you where they intersect.

Natasha (17:52)

Yeah, definitely. And I think maybe now is a good time to talk about your book. Hey, do I need a VA? Because I think one of the things I'm hearing and one of the things I see people struggle with, like we talked about earlier in the conversation is, you know, not only do I need a VA, but what type of VA do I need? And that might feel overwhelming listening to this conversation going, well, I don't know what kind of VA I need. So I'm guessing your book might have some instruction on that. So would love to hear about that.

Rachael Davila (18:18)

Thank you. So I wrote the...

I started my podcast first, Hey, Do I Need a VA? And what I realized is people learn different. Some people listen, some people need hands on, but some people like to do it themselves and read. And so I wrote the book because what I was finding and what I was hearing was a lot of well-meaning people saying, just hire a VA, just outsource it. A VA can help you with that, but they never told

anyone how to or what to look for and

outsourcing to another country may not be the right fit for all business owners. For those that it is, it's an amazing gift. But for those who don't need that type of VA, then they're stuck with what do I do? Aren't all VA's the same? We're not all the same. So the book really goes into detail over what kinds of support there are out there.

I'll share briefly. So there are specialists. So people who do like web design or bookkeeping, there are specialists in those fields. ⁓ There's personal assistants. So if a lot of your tasks need to be done in real life, then you don't want a virtual assistant, you want a personal assistant. Some business owners need an employee. They want full time. They might want someone in house or they don't like to, they don't like, they might want someone like at their

back and call or something. But for those who are looking for broad administrative support, then there are doers and collaborators. And we've talked about those distinctions. But I think just knowing that the term VA doesn't, like it encompasses almost all of that, but

Look at your handoff list. So in in my book, I take people through how I would share to create their handoff list. Real quickly, do a brain dump.

Then look at the tasks on your list. they do, delegate, delete, or delay items? Do things are things you have to do. No one else can do it for you. You have to go to your doctor's appointment. You have to have the call with your client, right? Delegate items are things you could easily hand off to somebody else with some training and perfectionism shunted to the side. Delete items are things that no longer serve you or your business. You can just cross those out.

And delay items are things that feel important but aren't urgent. Maybe other things need to happen before you get to those. Once you have that, then you look at your delegate list and you run it through what type of person would be best to support that. A specialist, a personal assistant, an employee, or a VA, and which type of VA. And then based on that, that's the kind of support that you need.

when you're ready for a VA, then there are other things in the book that go into beyond who's gonna do those tasks. But I offer a referral service because finding these, you can go to your personal network, your community, if you're involved in networking, like I met Natasha through a networking event and we get to meet all kinds of people.

they might know of a VA. But then I have that referral service so that I can hear what you need and then share with you who could help with that.

Natasha (22:08)

Yeah, it sounds like your book is an amazing resource for someone considering this and feeling like they need more information. Where can they find your book and your podcast?

Rachael Davila (22:17)

So my podcast is Hey, Do I Need a VA on all major podcast platforms. ⁓ My book is on Amazon in ebook format and the paperback is on all major retailers.

Natasha (22:32)

Awesome. That's great. And

is there anything about your services and what you do that we haven't discussed that you want to share with our audience?

Rachael Davila (22:38)

If you're on the journey to find a VA, even if you're just starting to think about it, you don't have to go on it alone. I can help. I offer the referral service. If you are thinking you're close to figuring out what you want, but you want to talk it through, I offer a 90 minute talk it through session. And if you're like, I need that hands on support to go through the process, then I offer coaching for that.

Natasha (23:08)

Awesome.

And I love that as someone who comes from a corporate background, you know, when you're in a smaller business where you're either the CEO or you're the only person in your business and this is your first hire, not having that sounding board of other, you know, other people in your company can be intimidating. So this really is a good way to outsource and probably save yourself some time and money because when you do make a mistake in hiring, it can be, you know, months down the drain, depending on how that goes.

Rachael Davila (23:36)

But I also encourage, even if you've gone down that route and it didn't work out, please come back. Not all VUs are the same. We got you. We can help. If a VA is the right fit, right? Obviously, if you need an employee, that's probably not the right idea. there is always something to learn in the struggle. So let's look at that and see what might be better for you.

Natasha (24:01)

Yeah. And I think this conversation has been great helping, ⁓ get an idea of who you might need to hire and some resources to actually make those first steps. And as we wind down this conversation today, I would love to ask you, a question I ask everyone, which is what's one piece of advice you would love to give your younger self? This can be business, personal, just something for our audience to reflect on.

Rachael Davila (24:23)

grace for yourself. You're not, there's so much you don't know that you don't know and to just give yourself grace that when you learn it, if it was a struggle, just what was it trying to teach you and it's not a,

personal value flaw, it's just a lesson to learn. It's just something to take into account and move forward with.

Natasha (24:53)

Yeah, I think that's a great place to end today because if you're an entrepreneur, you better be open to some growth because it's lots of failures and lots of things you don't know. And it just gets bigger. You just elevate and get bigger problems the more you go, but they're all good.

Rachael Davila (25:09)

And you might learn the same lesson because, right, they, someone said it's kind of like a spiral staircase that goes up, but it widens out, right? You might, the same lessons might keep coming back, but they're just there to remind you of how far you've come and how far you can go.

Natasha (25:27)

I'm

so true. So I'll go ahead and link the resources we talked about today in our show notes. And I just want to thank you for coming on and helping our audience today. It's been wonderful.

Rachael Davila (25:39)

Thank you, Natasha. Thank you, everyone.

Natasha (25:42)

Bye everyone.