As your freelance business grows, you’ll inevitably hit that point where there simply aren’t enough hours in the day. You’re juggling client work, emails, calendar management, social media, invoicing, and a dozen other tasks that seem to multiply daily. The logical next step? Hiring a virtual assistant.
But here’s where many freelancers get stuck: they have a laundry list of unrelated tasks they want to delegate, and they’re not sure what kind of person to look for or where to start. Should you find a specialist? A generalist? What tasks should you hand off first?
Key Takeaways from this Episode:
- Start by evaluating character over technical skills—look for honesty, personal responsibility, punctuality, and genuine care for your business
- Delegate low-stakes, high-frequency tasks first (like email and calendar management) to get the most time back with the least risk
- Use platforms like OnlineJobs.ph to find reliable Filipino professionals who often excel at diverse administrative work
Character Trumps Capabilities Every Time
When Austin Church was looking to hire his first virtual assistant, he took an approach that might surprise you. Rather than focusing on technical skills or specific experience, he prioritized character above all else.
“I think you start with character,” Austin explains. “By character, I mean honesty, personal responsibility, punctuality, and a concern for other people.”
This philosophy makes perfect sense when you think about it. Does it really matter how skilled someone is at managing your email if they’re dishonest? Can you truly scale your business with someone who doesn’t take responsibility for their mistakes?
Austin’s VA, Bern, is a perfect example of this approach working. When he hired her four and a half years ago, she didn’t know how to do most of the things she handles today. She had a government job in the Philippines and a college degree, but no specific experience with the tasks Austin needed done.
What she did have was character. She was honest, responsible, punctual, and genuinely cared about doing good work. Today, Austin can simply say “here’s the problem, figure it out,” and trust that Bern will find a solution—often a better one than he would have devised himself.
The Power of Teachability
Technical skills can be taught. Character cannot—at least not easily or quickly. When evaluating potential VAs, look for signs of teachability and initiative:
- Do they ask thoughtful questions during the interview process?
- When presented with a problem, do they show curiosity about finding solutions?
- Are they comfortable admitting when they don’t know something?
- Do they demonstrate a willingness to learn new systems and processes?
The right person will show genuine interest in understanding your business and finding ways to contribute, even in areas where they lack experience.
Where to Find Quality Virtual Assistants
Austin swears by OnlineJobs.ph, a platform specifically for connecting with Filipino professionals. He’s had consistently positive experiences and recommends it to all his coaching clients.
“There are some very specific cultural and language factors that I think make the chemistry really good between freelancers and entrepreneurs and Filipino workers,” he notes.
The Philippines places a high value on post-secondary education, so you’ll often find well-educated, intelligent professionals who are eager to work remotely for international clients. The combination of strong English skills, cultural alignment with Western business practices, and genuine work ethic makes this an excellent talent pool for most freelancers.
The Low-Stakes, High-Frequency Framework
Now comes the crucial question: what should you delegate first? Austin’s approach here is brilliantly strategic. He uses what he calls a frequency versus profitability matrix.
Think about your tasks in two dimensions:
- Frequency: How often does this task recur?
- Stakes: How directly does this impact revenue or client satisfaction?
The sweet spot for initial delegation is tasks that are high-frequency but low-stakes. Email management is a perfect example. You get tons of emails, they consume significant time, but if your VA makes a mistake, it’s easily correctable.
“I could probably train someone to manage my inbox and do a pretty good job at that, and I could train them to do that pretty quickly,” Austin explains. “And so it’s low stakes. If there are emails that they’re not sure how to answer, they put those in a folder for me to handle.”
Smart Delegation Builds Toward Growth
This approach serves a dual purpose. First, it gets you immediate time savings with minimal risk. Second, it frees up your mental bandwidth to work on higher-level business development.
Austin’s system with Bern includes a simple escalation process. Any emails Bern isn’t sure about go into an “Austin” folder for him to handle. This ensures nothing falls through the cracks while allowing her to handle the majority of routine correspondence.
The time you save can then be invested in activities that actually move the business forward: developing better processes, creating systems, or focusing on revenue-generating activities like sales and client delivery.
Examples of Low-Stakes, High-Frequency Tasks Perfect for VAs
- Email management and filtering
- Calendar scheduling and management
- Basic social media posting
- Data entry and organization
- Online research
- Invoice creation and follow-up
- Community management for online groups
- Newsletter setup and formatting
These tasks are time-consuming but don’t require your specific expertise or creativity. They’re also relatively straightforward to systemize and train.
Building Systems for Future Growth
As your VA proves themselves with these foundational tasks, you can begin delegating more complex responsibilities. But here’s the key: use that initial freed-up time to document your processes.
Austin suggests recording yourself while doing higher-stakes work—like writing copy or managing client relationships—and narrating your decision-making process. Your VA can then help turn these recordings into training materials and checklists for future hires.
This approach sets you up for sustainable growth. Instead of just hiring another version of yourself (which rarely works well), you’re building systems that allow multiple people to deliver consistent results.
The Long-Term Vision
Remember, the goal isn’t just to get tasks off your plate—it’s to build a business that can grow beyond your personal capacity. By starting with character-based hiring and strategic delegation, you’re laying the foundation for that growth.
Austin’s relationship with Bern exemplifies this progression. What started as basic administrative support has evolved into a true partnership where she manages complex projects and helps solve business challenges.
“These days I say, here’s the problem, figure it out,” Austin shares. “And that is sometimes all I have to say. She’s told me this is the best job she’s ever had, and ‘I love figuring things out.'”
When you find the right person with the right character, and you delegate strategically, you’re not just hiring help—you’re building the foundation for a scalable business.
The key is starting with character, delegating smart, and using your newly freed time to build the systems that will support your long-term growth. Get this foundation right, and hiring your first VA becomes the first step toward building something much bigger than just another freelance gig.
Episode Transcript
This transcript was generated automatically and may contain errors.
Preston (00:01.137)
Hello and welcome back to another episode of Freelance to Founder where we help you start freelancing, grow your agency and live the work life you’ve always wanted. You can send in your questions to be answered on this podcast at freelancetofounder.com slash ask. We have a cool new voicemail feature there. You can just record your question or you can type it up and send it in an email. I’m Preston. I started freelancing in college. From there I’ve built, grown or sold multiple successful businesses and together with my co-hosts, I’m ready to help you do the same.
If you’re ready to grow your service-based business to something bigger and you’re ready to become a founder, this show is for you. We’re here answering your questions every single weekday. Today I’m joined by my friend Austin Church. He’s the founder of the Freelance Cake Community for Advanced Freelancers and he’s the author of the book, Free Money. Hey again, Austin.
Austin L. Church (00:48.578)
Thanks for having me. I’m so happy to be here.
Preston (00:51.599)
Absolutely, Austin’s with us all week. You’ve maybe heard Yesterday and the day before a couple of episodes with Austin. He’s fantastic And we’ve had a couple of great conversations so far. We’re gonna jump into the question at hand today If I can pull it up here This is what live radio looks like. Let me find this We’re not actually live I’m gonna cut this out where to go
Darn it, this means more editing for my editing.
Austin L. Church (01:23.192)
Sorry, editor.
Preston (01:24.689)
Sorry. Sorry, Jason. Let’s see. Where did I, where did I lose the questions? There they are. Got a million windows open. I’m sure you don’t know anything about that.
Austin L. Church (01:38.082)
know a lot about that.
Preston (01:39.623)
Okay, here we go. We’re going to jump into today’s question. Today’s question comes from Elena Gaines. She says, I want to hire a VA, a virtual assistant to help me with a lot of different things that I have that have nothing to do with each other. I look for what kind of VA should I look for and what should I delegate first? So there’s a couple of questions to unpack here, Austin. First question is,
I have a lot of different tasks. They’re not really related, but I want to hire a VA or a virtual assistant. What should I look for in someone who has to do a lot of unrelated tasks? you, Austin, do you have, I think you have an assistant because as I was emailing you to have you on the show, someone emailed me back that wasn’t you. Is that right?
Austin L. Church (02:26.606)
That’s right. She has been with me, I think, four and a half years now.
Preston (02:31.641)
wow, nice. What kind of work does she do for you? Can we say her name on the air?
Austin L. Church (02:36.076)
Yeah, her name is Bern, B-E-R-N and.
Preston (02:39.761)
Shout out to Burn and what kind of stuff does Burn do in your business?
Austin L. Church (02:43.52)
She does a lot. It’s everything from answer emails, as you already mentioned, to managing my calendar. I have a community that you mentioned called the freelance kit community. It’s for advanced freelancers. She does community management. She does a lot of online research. She sets up my newsletter every week. She interfaces with freelancers and contractors. So I think she kind of fits the bill described in the question. She does.
Preston (03:12.687)
Yeah, she does a lot.
Austin L. Church (03:13.078)
A whole bunch of unrelated things for sure.
Preston (03:16.241)
So how did you find her?
Austin L. Church (03:18.198)
So I went through a site called online jobs dot pH. The site only shows profiles for professionals in the Philippines. And I have only had a positive experience using the site. It’s the site that I recommend to all of my one-on-one coaching clients. And I mean, I don’t think we have time in this episode to unpack.
why I think Filipino professionals, people, workers, VAs are so amazing. There are some very specific cultural and even language factors that I think make the chemistry really good between freelancers and entrepreneurs and Filipino workers. But I only say that to say, I don’t think.
we can go wrong most of us hiring someone in the Philippines specifically. And then, yeah, we can break down hiring if you like, or kind of address the question other ways.
Preston (04:22.254)
Yeah, let’s talk. Yeah, yeah, yeah. So she asks, what should I look for in a good VA? So I’m curious, like, what were you looking for when you found Byrne? Elena’s wondering what kind of things should be on my maybe must have list or just generally what should she be looking for, think?
Austin L. Church (04:42.318)
So I’m going to take an unusual angle here and say, I think you start with character. And by character, mean honesty, personal responsibility, punctuality, or timeliness, and a concern for other people. You get a sense of character based on interview questions that you ask. And I start with character because honestly, does it
really matter how good someone is at managing your email if they’re dishonest. So we so often try to hire for skills first when skills are inconsequential or irrelevant if you hire someone who steals from you or lies to you or like hurts your business in a material way. first and foremost, I think we’re trying to find people
Preston (05:17.734)
Yeah, that’s so wise.
Preston (05:31.937)
All right. Yeah.
Preston (05:36.741)
Hmm.
Austin L. Church (05:41.558)
who genuinely care about us, genuinely want to serve us and do a good job are loyal. Like that’s another aspect of character, right? They want to, want to stick around and the honesty thing, if they make a mistake, they own up to it. And then they’re like, and here’s what I’m going to do to make it right. That’s personal responsibility. If you make a mistake, are you trying to make it right? So
Preston (05:51.77)
Mm-hmm. Mm-hmm.
Preston (06:00.507)
Hmm.
Austin L. Church (06:08.738)
Bern didn’t know how to do most of the things she now does when she first started working for me. She had a government job in the Philippines. Now she did have a college degree. What you’ll find in the Philippines and one of the things that makes that country special is there’s a very high value placed on post-secondary education. So going to college. So she’s very well educated. She’s very intelligent.
Preston (06:32.25)
Mm-hmm. Mm-hmm.
Austin L. Church (06:38.196)
And yet because opportunities being what they are in the Philippines, she was very interested in working remotely for someone outside of the country. Right. And because of her, who she is, we’ve worked really well together. So it’s not like, Bern’s story would fit everybody who needs to hire a VA. My point is, can you evaluate character in some way before you hire?
Preston (06:49.016)
Yeah.
Austin L. Church (07:08.018)
Knowing that the right person will show initiative, they will be versatile, they will take initiative, they will go figure things out. These days with Bern, I don’t say, here’s what I need you to do and exactly how to do it. These days I say, here’s the problem, figure it out. And that is sometimes all I have to say. And she’s like, great. And she has told me one, this is the best job I’ve ever had.
Preston (07:24.368)
Hmm.
Here’s the end result I need. Yeah.
Austin L. Church (07:38.158)
And two, I love figuring things out. So we have grown together and yeah, I give her really specific instructions when I know that’s going to serve her. But sometimes I’m like, here’s the outcome. I’m going to get out of your way. Let me know when it’s finished. And that’s exactly what happens.
Preston (07:53.723)
Yeah, yeah. And quite often what I have found is, like someone you’re working with, especially someone you’ve been working with for a long time, they’ll actually find a better solution than how you would have laid out, you know, a standard operating procedure procedure or something like you, you just give them a solution and end result. You trust them quite often. They will find an even better way to do it than you would have found this. I agree with you for me. a lot of, a lot of these things are checking my box as well. I look for yes character.
I look for teachability and you kind of touched on this where it’s like, I can’t teach you or I don’t want to teach you personal relationship skills. I can’t teach you to be a good person or I don’t want to, but I can teach you email marketing, right? I can teach you the technical side of setting up a newsletter. can…
Austin L. Church (08:38.958)
Hmm.
Austin L. Church (08:47.266)
Mm-hmm.
Preston (08:47.854)
I can even help you be a better copywriter. Like some of those technical skills, and this is so interesting, because if you think back to our conversation on Monday, we talked about pricing and Cameron was asking like, how do I raise my rates? Isn’t this so interesting? We haven’t even talked about that yet. We haven’t, and we haven’t talked about like hourly rate, technical skills. We’re talking about the stuff we really value, which is personal character, personal integrity, ability to learn.
Austin L. Church (09:03.502)
Mm-hmm.
Preston (09:14.63)
Go go giddiness, right? If a person will just take a problem run with it and find a solution like these are all things that you and I pay a premium for there are cheaper people we could hire but we pay a premium for people who we know we can trust who we know will get things done and And so it’s just really interesting to watch these two conversations the one we had on Monday and the one we’re having today how they’re sort of intersecting
Austin L. Church (09:25.142)
Mm-hmm.
Preston (09:42.042)
We’re going to take a quick break for a message from our sponsors. After we get back, I want to answer the second half of this question, which is what should I delegate to my VA first? So we’ll be right back after this quick break.
Preston (10:00.816)
All right, I am here with Austin Church. My name’s Preston Lee. This is Freelance to Founder. And we’re answering Elena’s question. She wants to hire a VA, but she’s not sure what to look for in a VA. That was the first half of the episode. Now we’re gonna take just a few minutes and answer the second half of her question, which is, what kind of thing should I delegate first to my VA? So I’m curious when you hired Burn, Austin, who we talked about in the first half, what did you initially hire her for? Like what were the first few tasks you gave her?
Austin L. Church (10:28.216)
So can I share a little quadrant that I use first? OK, so we all, and you mentioned in another episode doing like a time and energy audit. And so if you do that, our temptation is to say, OK, what are the things that are consuming all my time? And often it’s project work. And so when we go and we hire help,
Preston (10:32.806)
I love this.
Austin L. Church (10:57.184)
or we get more support, we’re looking for a mini me and we’re like, okay, who can do design or who can do writing or who can do whatever? And I think it’s better to actually use this matrix I’m gonna describe where first of all, you think about frequency. So like, how often does this task recur? Right? And so something that recurs or happens a lot is email. So emails, you just get a lot of them.
Preston (11:04.006)
Yeah, yeah.
Austin L. Church (11:26.504)
and you spend a lot of time answering them, right? And then if you think about, let’s just call it profitability, right? So there are certain things that make a direct financial impact on your business. And you may not like doing all of them, but if you keep doing them, the business keeps making money. And as much as you would love to delegate some of it,
Maybe you can’t right away, but my point is don’t delegate right away the things that are higher stakes because they mean you either make money or don’t make money. Assuming, you know, they’re done well, right? Because you may have process that you follow and process that’s hard to teach. Like what makes good copywriting good? What makes good design good? And you go and hire a designer and you actually like,
Preston (12:03.974)
Yeah.
Austin L. Church (12:23.564)
I’m just not pleased with the work that this subcontractor did for me. Now what? I think the better strategy is what are the tasks that are low stakes and high frequency? So yeah, I could probably train someone to manage my inbox and do a pretty good job at that. And I could train them to do that pretty quickly.
Preston (12:40.838)
Hmm.
Austin L. Church (12:52.946)
And so it’s low stakes. And if there are emails that they’re like, I just wasn’t sure how to answer that. Sure. You put that in the folder. And for me, it’s exclamation point Austin. So if there are certain emails that burn doesn’t know quite how to approach, she just lets me answer those. She’s like, it seemed high stakes. You do it right. So you get back more time more quickly. If you delegate first high frequency tasks.
Preston (13:12.294)
Hmm.
Austin L. Church (13:22.732)
and you actually lower risk in your business overall if you don’t delegate like the money making revenue producing tasks quite yet. So I think about this in terms of phases or stages. Phase one, how do you get back as much time as possible by delegating low stakes, high frequency tasks? And that’s where I recommend people start. Inbox management.
Preston (13:51.43)
That’s really interesting. Yeah, yeah.
Austin L. Church (13:52.654)
calendar management, some others, but yeah, say what you were gonna say.
Preston (13:56.197)
Well, I just think it’s interesting because I wish we had Elena here to ask a follow-up question because to me it depends on, are you looking to save time? Are you looking to rescue time? Are you looking to increase revenue? And sometimes those go hand in hand. Sometimes if you can rescue your own time, if you’re the main revenue generator in your business, which most freelancers or even agency owners tend to be,
then of course freeing up some of your time is gonna free up opportunity for you to make more money for the company. But it’s interesting, because if you look at it that way, you’re hiring completely different people, right? If you hire, and this is maybe outside the realm of VA, we’re just talking about hiring generally. But if you hire someone who does project work, that could free up your time to do more sales and that could boost revenue. If you hire someone to help with these frequent,
but low stakes, which I love that concept, these frequent but low stakes tasks, then you’re freeing up your time, but then that doesn’t necessarily increase your ability to make more sales if you are still swamped with project work. So it kind of depends on like, you know, where are you feeling pinched? Where are you feeling like time or effort are tight, always taken up and maybe freeing up some of those.
It’s almost like every business you have to look at independently and say, here’s where if I had more time or effort to devote myself, here’s where we could make way more money or here’s where the business could grow faster.
Austin L. Church (15:31.0)
So.
Austin L. Church (15:34.314)
If you are wanting to increase revenue, there’s like this gotcha. And the gotcha is, well, that assumes that outcomes and client experience are going to stay consistent. Like, Hey, we can’t, we don’t want to scale up dissatisfied clients. So when we talk about growth or revenue growth, we’re saying, yeah, let’s do bigger projects for the same clients.
Preston (15:47.63)
Hmm, very true.
Preston (15:53.317)
Right.
Austin L. Church (16:01.696)
or let’s do projects of the same size for more clients, either way, we need to maintain consistent work quality and consistent client experience. Well, the only way to do that if you’re bringing in subcontractors is to work from a consistent system with consistent processes. Have you as the business owner defined those? So a lot of people in the situation of the person asking this question, they do
Like if they’ve got more project work than they can handle, it seems totally logical to go hire a mini me and say, great. Now I can take on twice as many writing projects because I have this other writer working for me, except their process is different than yours. And their quality is going to be different. Their style is different. Right. So I still think the best way to increase revenue is to.
Preston (16:46.18)
Right. And their quality is going to be different and their style is going to be different. Yeah.
Austin L. Church (17:00.268)
free up your time first, then what do you do with that freed up time? Now you actually define your creative processes. So that, and your business processes. And here’s the thing, your VA can help you do that too. Like for example, you’re writing some copy and you’re just sort of narrating how you’re writing copy and the choices that you’re making.
Preston (17:10.596)
and your business processes. Yeah.
Preston (17:16.613)
Yeah.
Austin L. Church (17:26.604)
Well, not only can that video now become a training video for a copywriter you hire. Well, maybe you say, and here’s the checklist I use always. And like, don’t ever send a client a draft of copy before you run spell check, before you read it out loud, like you’re running through this checklist. Your VA can take your video and turn it into a checklist. So when you onboard a new copywriter, they have the video, they have the checklist.
And you’re just going to experience a lot, you know, many fewer headaches. I don’t know if that is the right way to say it in English, many fewer, but fewer headaches, right? But you will have an easier time producing consistent outcomes for clients as you grow. If everybody’s working from the same process.
Preston (18:04.27)
Yeah.
Preston (18:17.55)
Yeah, I love the idea of freeing up your time to then work on the business instead of in the business, right? We talk about, and we’ve talked about a ton on this show about like, have you built yourself a job or are you building yourself a business? And if you’ve built yourself a job, a VA or any second hire or first hire or whatever can be a great way to free up that time that you feel pinched to where you can say, I’m going to take a step back. I’m going to think about this business a year from now, five years from now, 10 years from now.
I’m going to start doing those things that are going to make an impact long term to where I’m not stuck doing the same thing for 20 years and have nothing to show for it. So working on your business instead of working in your business. Austin, this has been super helpful today. We hope, Elena, this has been helpful to answer your question. I’ve been Preston with Milo, of course, Austin Church from Freelance Cake, the community and the book Free Money. We’ll be sure to link up everything of Austin’s in the description of this episode. But thank you so much for joining me again today,
Austin L. Church (18:50.028)
Yes.
Austin L. Church (19:16.63)
It’s been fun.
Preston (19:18.158)
All right, we will talk to you guys next time. You’ve been listening to Freelance to Founder. We’ll see ya.
