How I Hired My First Virtual Assistant (And What I Wish I Had Known Sooner)

TL;DR

• I was the bottleneck.

• I hired a virtual assistant.

• I reviewed 103 applicants so you don't have to.

• A great job description beats a great resume.

• The right VA protects revenue, improves operations, and creates headspace.

One afternoon, I was sitting in my car after an all-day client project, answering emails before heading straight to my son's two-and-a-half-hour baseball game. It was one of those moments where I was trying to cram an hour's worth of work into twenty minutes.

There were website leads I needed to follow up with. An estimate I still hadn't sent. A scheduling change from a team member. Three client emails waiting for responses. A hiring task I had promised myself I'd tackle that week. A hauler I needed to schedule for an upcoming project. An Elfa order that needed to be placed.

Nothing on the to-do list was difficult. In fact, most of it would have taken less than ten minutes to complete. The problem was that every day, there were dozens of those ten-minute tasks stacked on top of each other, all waiting for me.

I wasn't overwhelmed by the work itself. I was stuck, and that's when it finally hit me: I wasn't the hardest-working person in my business. I was the bottleneck.

A few months later, I hired my first virtual assistant. Looking back, I should have done it six months sooner.

Hiring a virtual assistant was one of the most important hires I've made for The Organized House. It was also one of the most intimidating because, like most small business owners, I didn't have unlimited money to spend, and I definitely didn't have unlimited time to find the right person.

Since hiring my virtual assistant, Courteney, I've realized that a lot of home organizers and service-based business owners are wrestling with the same questions I was.

• When you're ready to hire?

• Where do you start looking?

• How much do you pay someone?

• What should you hand off first?

• How do you know if someone is actually the right fit?

It took me about 45 days to hire a virtual assistant, and there were definitely a few hiccups and lessons learned along the way. In the end, though, I found someone who has become an incredible asset to The Organized House.

I thought I'd share exactly how I approached the process, what worked, what didn't, and what I'd do differently if I were hiring again. Throughout this post, I've outlined the exact steps I took, along with practical tips and recommendations that may help you avoid some of the mistakes I made.

And because I've been asked many of the same questions by fellow home organizers and small business owners, I've also included a FAQ section at the end.

I hope this serves as a helpful resource if you're considering hiring a virtual assistant of your own.

Before You Hire a Virtual Assistant, Figure Out What's Actually Broken

I think most people start the hiring process backward. They start by looking for a person when they should start by looking for the problem.

When I first began thinking about hiring a virtual assistant, I kept telling people that I needed "help with my inbox." The more I looked at the business, the more I realized my inbox wasn't actually the problem. It was simply where the symptoms were showing up.

The real issue was that too many important business functions depended on me.

I spent a lot of time thinking about what I actually needed from a virtual assistant.

As I evaluated how I was spending my time, I began to separate the business into categories. Some responsibilities directly impacted revenue. Others impacted operations. Others were simply administrative tasks that needed to get done.

The area that needed the most attention was the top of the funnel.

Website inquiries need responses. Consult calls need scheduling. Potential clients need follow-up. Estimates need to be sent. If any of those things were delayed, it didn't just create more work for me—it potentially impacted revenue.

At the same time, operational responsibilities kept the business moving. Team communication, scheduling adjustments, hiring support, project coordination, and follow-through all require attention. None of those tasks were particularly difficult, but together they created a constant stream of work that relied heavily on me.

That's when I realized I wasn't looking for a minion or someone to simply answer emails. I was looking for someone who could help protect revenue, improve operational efficiency, and create more consistency throughout the business.

If you're considering hiring a virtual assistant, I'd encourage you to look beyond the tasks themselves and ask a bigger question: What areas of the business slow down when you're busy?

For me, the answer was clear. The top of the funnel and several key operational functions needed more structure, more consistency, and less dependence on me.

That realization became my hiring roadmap.

Write a Stellar Job Description

Before you start asking for referrals, contacting your network, or posting a job on Indeed, write your job description.

Not a rough outline or a random list of tasks. An actual job description.

I can't stress this enough because your job description becomes the filter for everything that comes next. The quality of your applicants is often a direct reflection of the quality of your posting.

When I first started looking for a virtual assistant, I wrote something along the lines of, "Looking for a virtual assistant to help with administrative tasks, scheduling, and business support."

Very quickly, I realized that was far too vague.

• What administrative tasks?

• What kind of scheduling?

• What does business support mean?

The problem wasn't that I couldn't find applicants. The problem was that my description was so broad that almost anyone, regardless of experience, could see themselves applying for the role.

The more specific you are, the better your applicant pool becomes. The more vague you are, the more applications you'll receive from people who aren't actually qualified for the role.

Remember all that work from the previous section about identifying your bottlenecks? This is where it becomes useful.

Instead of writing "manage inbox," be more specific. Write something like, "Respond to daily website inquiries and nurture leads through the sales process."

Instead of writing "scheduling," write, "Schedule consult calls, project sessions, reminders, and team availability."

Instead of writing "administrative support," write, "Coordinate project details, update SOPs, assist with hiring workflows, and follow up on outstanding tasks."

Those are very different descriptions. One attracts people looking for "a VA job." The other attracts people who can picture themselves doing the actual work.

I would also encourage you to be honest about the type of person you're looking for. In my posting, I wasn't looking for someone I could train from scratch. I wanted someone with previous virtual assistant or executive assistant experience who could operate independently, communicate professionally, and help move things forward without adding more to my plate.

There is no right or wrong answer here. Some business owners love training and mentoring, but at this stage of my business, I knew I didn't have the bandwidth for that.

The goal isn't to write the perfect job description. The goal is to write an honest one.

A strong job description should include responsibilities, required experience, desired experience, hours per week, pay range, time zone expectations, software and tools used, communication expectations, and what success looks like in the role.

One thing that helped me tremendously was imagining that my future assistant was sitting across from me at a coffee shop. What would I tell them about the position? What would I expect them to own? What tasks did I no longer want to do every day? When I opened my email in the morning, what would make me relieved? What would make me thrilled six months from now?

The answers to those questions belong in your job description.

If you'd like to see the actual job description I used when hiring my virtual assistant, you can find it here.

If you're struggling to write your own, try this ChatGPT prompt

"Act as an experienced hiring manager for a small service-based business. Help me write a virtual assistant job description. My business is [describe your business]. I need help with [list your bottlenecks and responsibilities]. Ask me any questions you need before drafting the posting. Then create a complete job description that includes responsibilities, qualifications, desired experience, hours, communication expectations, and what success looks like in the role."

Don't be afraid to revise your posting several times. I did. Even after the job was already live.

A strong job description won't guarantee the perfect hire, but it will dramatically improve your chances of finding the right people and save you hours sorting through the wrong ones.

Where To Find A Virtual Assistant

Once I knew what I needed, I reached out to a trusted Facebook group of Portland, Oregon, female business owners that I've been part of for years.

This was the first outreach. I started with a very generic ask. That quickly changed.

Within a day, I had roughly a dozen recommendations. Most of them fell into one of two categories: independent virtual assistants or agencies, many of which referred to themselves as boutique agencies.

Initially, I thought I wanted an agency. There was something reassuring about having a company behind the person. It felt safer, more established, and more professional.

As I started having conversations, though, I quickly learned there were trade-offs.

The first was cost. The agencies I spoke with ranged from roughly $65 to $90 per hour. That's not unreasonable. They have recruiting costs, management costs, training costs, and overhead. The question isn't whether they're worth it. The question is whether they're worth it for your business right now.

The second consideration was time zones. Many agencies assign assistants across the country or around the world. For some businesses, that's actually an advantage. If you need overnight work completed or round-the-clock coverage, that can be a great fit.

For me, it wasn't ideal.

My business is local to Portland, Oregon. Our clients and team need speedy answers about projects, scheduling, organizers, products, and logistics. I wanted someone whose workday looked similar to mine.

One thing I recommend is making a list of your non-negotiables before you start interviewing. Mine included

• being U.S.-based

• having at least three years of virtual assistant or executive assistant experience

• strong communication skills

• understanding and confidence with technology

• the ability to work independently

• availability during my business hours
  

Knowing those requirements saved me from spending time on candidates who weren't the right fit.

The Agency That Taught Me a Valuable Lesson

There was one agency I genuinely wanted to hire.

Their mission was incredible. They primarily worked with moms returning to the workforce and looking for flexible opportunities. As a working mom, I loved everything about that.

Unfortunately, the experience highlighted something important.

Communication was slow. Really slow.

It took weeks to receive the information I requested. I had to follow up multiple times for a proposal. Once the proposal arrived, communication largely disappeared.

That experience taught me something I still think about today: the hiring process is often a preview of the working relationship.

Pay attention to how people communicate before you hire them. If emails take a week to answer now, they probably won't magically become faster later.

For me, I'd rather continue doing the work myself for a little longer than hire someone who creates more uncertainty, more follow-up, and more work on my end.

My Indeed Job Posting

When the referral and agency route wasn't producing the results I wanted, I decided to post a paid job on Indeed. I also made a post on LinkedIn and asked my network if they knew anyone looking for a virtual assistant role. That generated some interest, but most of the people who reached out were looking to switch careers and believed their skills would transfer well.

The problem was that I wasn't looking for potential. I was looking for experience.

Everyone can tell you they're organized. Everyone can tell you they're good at communication, scheduling, and managing an inbox. But being a virtual assistant is a skill set. There is a big difference between someone who believes they can do the work and someone who has already done it successfully.

Over the next two weeks, I received 103 applications. The posting cost me $55.12, and within the first 24 hours, I had received 20 applicants.

At first, I thought that was fantastic. Then I realized I had to read every single application.

That's when I learned one of the biggest lessons of the hiring process: your job posting and screening questions matter more than you think.

The clearer and more specific your posting is, the better your applicant pool becomes. That doesn't mean everyone will read it. Trust me, they won't. Some people will skim it. Some won't read it at all. And some will apply even if they don't meet the qualifications you've outlined.

I found that incredibly frustrating because I knew exactly what I was looking for, but overall, Indeed ended up being the fastest and most effective way for me to build a large pool of candidates. The key wasn't getting more applicants. The key was getting clearer about who I was actually looking for.

The Screening Questions That Saved Me Hours

One of the best things I did was add screening questions to my Indeed posting.

When I first posted the job, I was getting applications from everyone. People with no virtual assistant experience. People who clearly hadn't read the job description. People who either ignored the requirements or hoped they could talk their way around them.

I quickly realized I was spending a lot of time reviewing candidates who were never going to be a fit.

That's when I added screening questions, and it completely changed the quality of applicants. The questions forced people to slow down, think about their answers, and demonstrate why they were qualified for the role. It helped separate the people who were intentionally applying for this position from the people applying to every job they could find.

One of the questions I asked was, "Have you ever been a virtual assistant? If so, how many years?"

This was important because prior experience as a virtual assistant or executive assistant was one of my non-negotiables. At the same time, it gave applicants an opportunity to tell their story. Some people had never held the title of virtual assistant but had relevant experience supporting executives, managing projects, or coordinating operations. If prior experience matters to you, I would absolutely recommend asking a version of this question.

Another question I asked was, "Tell me about a time you improved a process without being asked."

For me, this question was gold. I wasn't looking for someone to simply complete tasks. I wanted someone who could identify inefficiencies, think critically, and help make the business run better. The answers told me a lot about a person's experience level, confidence, and ability to take initiative.

I also asked, "Describe the type of manager you work best with."

This question had less to do with skills and more to do with fit. Every business owner has a different management style. Some are highly structured and hands-on. Others are more collaborative and give a lot of autonomy. I wanted to understand what environment helped each applicant do their best work and whether that aligned with how I operate.

What surprised me most was how much I learned from the answers. In many cases, the responses told me more than the resume. Some applicants had impressive experience on paper but gave short, generic answers. Others had less traditional backgrounds but demonstrated strong communication skills, initiative, and thoughtful problem-solving.

If you're hiring, don't think of screening questions as a hurdle for applicants. Think of them as a window into how someone thinks. Skills can be taught. Curiosity, communication, and initiative are much harder to fake.

How I Used ChatGPT During the Hiring Process

I know some people will love this and others will hate it, but ChatGPT has become one of my favorite hiring tools.

Whenever I found a candidate who looked promising, I would upload their resume, screening questions, and my job posting. Then I would ask:

"Act as a hiring manager. Compare this candidate to my job description. Identify strengths, concerns, skill gaps, and five interview questions I should ask."

It wasn't making decisions for me. It was giving me another perspective.

Several times, it highlighted things I had completely overlooked. Sometimes it pointed out experience that was highly relevant but buried deep in a resume. Other times, it identified gaps between what I was looking for and what the candidate had actually done. It also helped me create thoughtful interview questions based on each person's background rather than asking everyone the exact same thing.

One thing I want to stress is that ChatGPT never made a hiring decision for me. It was simply another set of eyes. Just like I might ask a trusted business owner to review a candidate, I used ChatGPT to help me slow down and look at applicants more objectively.

If you're hiring, use it as a tool, not as a decision-maker. Upload the resume, the job description, and the applicant's responses, then ask where it sees alignment, where it sees concerns, and what questions it would ask during an interview.

The final decision should always be yours, but I found it incredibly helpful for spotting things I might have otherwise missed.

How I Knew My Virtual Assistant Was the Right Person

Out of the 103 applicants, I reached out to just 18 people. In other words, I rejected more than 80% of the applicant pool before ever getting on a Zoom call. Six of those 18 never responded, which narrowed the field even further. I was also considering four virtual assistant agencies that had been recommended to me.

From there, I conducted Zoom interviews with cameras on. Part of that was practical. We live in a Zoom world, and I wanted someone who was comfortable using the technology and communicating professionally through a screen. But I also wanted to see how they carried themselves, how they communicated, and whether I could picture them interacting with clients, vendors, and the rest of the team.

One recommendation I would make is to pay close attention to the questions candidates ask during the interview. Most people spend the interview evaluating the candidate, but the candidate's questions can tell you just as much as their answers.

Within the first few minutes of speaking with Courteney, I knew she was different.

What stood out wasn't her resume or even her experience. It was how she thought.

She wasn't asking basic questions or focusing only on the tasks she would be responsible for. She was asking about workflows, communication, and how information moved through the business. She wanted to understand where things were getting stuck, what my bottlenecks were, and how she could help remove them.

It was clear that her goal wasn't to create more work for me. It was to take work off my plate.

My opinion is that tasks can be taught. Systems can be documented. Processes can be improved. What's much harder to teach is the ability to see the bigger picture and understand how all the moving pieces work together.

If you're interviewing virtual assistant candidates, listen for questions like:

• What does success look like in this role six months from now?

• Where are you spending the most time today?

• What tasks are currently falling through the cracks?

• What would make this hire a huge win for you?

Those are the types of questions that tell me someone is thinking beyond the task list and trying to truly understand the business.

Courteney wasn't just trying to understand the job. She was trying to understand how the business worked, where I was stuck, and how she could help move things forward.

Plus, we just clicked. The conversation felt easy, natural, and productive from the start.

What I Delegated First

When it came time to start delegating, I went back to the list of bottlenecks I had identified earlier in the process.

I wasn't looking to hand over huge projects or major responsibilities right away. Instead, I looked for quick wins: tasks that were important, happened regularly, and already had a fairly clear process. All those ten-minute tasks that build up day after day and somehow end up taking hours of your week.

Courteney's first responsibilities included lead follow-up, consult scheduling, calendar management, team communication, and hiring support. These were all things that needed to happen consistently but didn't necessarily need to be done by me.

Just as importantly, she came in with experience. She had done similar work before, so I wasn't starting from scratch or spending my time explaining every little detail.

Starting there allowed us to build trust, establish workflows, and learn how we worked together before adding additional responsibilities. Looking back, it was the right approach for both of us.

What Has Changed Since Hiring a Virtual Assistant

I don't want to paint a picture of everything being perfect now, because it's not. I still miss things. I'm sometimes slow to respond to requests. There are projects that don't go exactly as planned. We still have busy weeks where we're trying to keep a lot of balls in the air.

What has changed is consistency and accountability.

Before hiring Courteney, there were simply too many things that depended on me remembering them. Leads needed follow-up. Estimates needed to be sent. Scheduling adjustments needed attention. None of those tasks were difficult, but they all competed for the same limited amount of time and mental energy.

Today, there is more structure behind the scenes. Our lead funnel is more organized. Scheduling is more efficient. Follow-up is more consistent. Most importantly, I'm no longer carrying every task, reminder, and next step around in my head.

Hiring a virtual assistant didn't create some massive overnight transformation, but it did create more consistency in the business and more headspace for me. That's been worth every penny.

Hiring Red Flags I Couldn't Ignore

As I worked my way through more than 100 applications, countless emails, and multiple interviews, I started noticing patterns. Some candidates immediately moved to the top of my list, while others quickly found their way into the "no" pile.

One of the biggest red flags was when someone immediately wanted to tell me everything that was wrong with my business. Don't get me wrong. I know there are things I can improve. Every business owner has a running list of things they'd like to do better. I wasn't looking for someone to point out problems, though. I was looking for someone who could help execute solutions. There is a big difference between someone who spends their time talking about what should be done and someone who rolls up their sleeves and helps make it happen.

Communication was another big one for me. If I had to repeatedly follow up to get information that someone promised to send, that was a problem. In fact, there was one candidate I liked so much that I almost offered her the job during our interview. Looking back, I don't recommend doing that. After the interview, I never received any follow-up from her.

Maybe I'm a little old school, but I still think a thank-you email matters. It doesn't have to be long or formal. It simply shows professionalism, interest, and follow-through. If someone struggles to communicate during the hiring process, it's hard for me to believe that communication will suddenly improve after they're hired.

I also found myself gravitating toward people whose resumes had personality and sounded like actual humans. After reading dozens of applications, the buzzwords start to blur together. Results-driven. Strategic thinker. Detail-oriented. Those descriptions don't tell me much. What caught my attention were the small details that helped me understand who someone was, what they had actually accomplished, and how they approached their work.

The candidates who stood out were the ones who felt genuine.

Another red flag was when applicants clearly hadn't read the job description. I had taken a lot of time to outline the experience, skills, and qualifications I was looking for. Yet many applicants either didn't meet those requirements or couldn't explain why they were interested in the role despite lacking the experience I had specifically asked for.

I'm all for taking chances on people, but there still needs to be a reasonable connection between the role and the applicant's background.

More than anything, though, I was looking for curiosity. The strongest candidates did their homework. They visited my website. They looked at my social media. They read through the blog. They asked thoughtful questions about the business, the clients, and the role itself. They weren't just trying to get a job. They were trying to understand whether they could genuinely contribute.

If I had to narrow everything down to one thing, that's what separated the good candidates from the great ones. The great candidates were curious enough to learn about the business before they ever asked to be part of it.

My Final Thoughts on Hiring a Virtual Assistant

Looking back, hiring a virtual assistant wasn't really about getting more things checked off my to-do list.

It was about creating space.

Space to focus on the parts of my business that actually need me, and space to stop feeling like every email, follow-up, scheduling change, and loose end depended on one person.

If you're considering hiring a virtual assistant, don't start by looking for a person. Start by identifying the bottleneck. Figure out what's slowing you down, what consistently falls through the cracks, and what someone else could take ownership of.

The right virtual assistant won't solve every problem in your business, but they can help remove the pressure of feeling like everything rests on your shoulders.

Hiring a Virtual Assistant Frequently Asked Questions

Since sharing my experience hiring a virtual assistant, I've received many of the same questions from fellow home organizers and small business owners. I thought I'd answer them here in case you're wondering the same thing.

Is your VA an employee of your business?

No. Courteney is a 1099 independent contractor.

That means she is self-employed and responsible for her own taxes, benefits, and business expenses. As the business owner, I pay her for the hours worked, but I don't provide employee benefits such as health insurance, paid time off, or retirement contributions.

Whether you hire someone as a W-2 employee or a 1099 contractor is something you'll want to discuss with your accountant, bookkeeper, or attorney to ensure you're following the rules that apply to your situation.

How much do you pay your virtual assistant?

I don't think Courteney would appreciate me sharing her exact hourly rate, so instead I'll share the range I posted in my job description: $30-$45 per hour.

One thing that helped me tremendously was determining what I could realistically afford before I started interviewing candidates. Talk with your bookkeeper, accountant, business coach, or financial advisor and understand what makes sense for your business.

I also spent time researching market rates. I asked ChatGPT, reviewed job postings, spoke with other business owners, and looked at agency pricing to understand what qualified virtual assistants were charging.

Remember, hiring a VA is an investment. Going with the cheapest option isn't always the best option, especially if you need someone who can work independently and contribute quickly.

How many hours does your VA work each week?

Currently, Courteney works between 5 and 10 hours per week, depending on lead volume, hiring needs, projects, and what's happening inside the business.

One of the biggest misconceptions I had was thinking I needed enough work to keep someone busy for 20 or 30 hours per week. That's simply not true. Starting with fewer hours gave us time to build trust, establish systems, and determine what responsibilities made the most sense to hand off.

I'll also be transparent: I'm at a stage in my business where I'm paying close attention to margins and expenses. Could Courteney take on more work? Absolutely. But for now, I'm being intentional about where I spend money while still getting the support I need.

Do you meet with your virtual assistant regularly?

Yes and no.

Courteney and I communicate almost every day. Sometimes it's a quick hello, update, or question. Other times, it's a more in-depth review of upcoming priorities.

When she first started, we met weekly via Zoom. Those meetings were incredibly helpful because they allowed us to build a relationship, work through processes together, and answer questions in real time.

As time went on, we needed fewer formal meetings because many of the systems and expectations had already been established.

One thing to remember is that every meeting has a cost. You're paying for your VA's time, and you're using your own. Make sure your meetings are productive and serve a purpose.

How did you onboard your virtual assistant?

Honestly, onboarding took longer than I expected because it forced me to document many of the systems and processes that had previously existed only in my head.

I created a three-part onboarding plan with specific objectives, topics, and responsibilities for each phase. Each phase was tied directly to the responsibilities I had outlined in the job description, which helped us stay focused and avoid getting sidetracked by day-to-day issues.

If there's one thing I learned, it's that onboarding isn't really about teaching someone how to do tasks. It's about teaching them how your business operates.

What was the first thing you delegated?

My inbox and calendar.

They were repeatable areas that already had a fairly clear process, which made them easier to hand off. Courteney started by helping manage and organize incoming leads, schedule consult calls, track when estimates were sent, coordinate calendar changes, and keep communication moving.

I intentionally avoided delegating large projects right away. Instead, I focused on smaller tasks that allowed us to build trust, establish workflows, and gain confidence working together before handing off more responsibility.

Couldn't AI and automation handle some of these tasks?

Absolutely. And in some areas of my business, I do use AI and automation. But when it comes to client communication, especially at the beginning of the relationship, I believe people deserve a real person.

If you're a home organizer, you know exactly what I mean. People come to us during incredibly personal seasons of life. Some are overwhelmed and embarrassed by the state of their homes. Some have just lost a spouse. Some are navigating a divorce, a cancer diagnosis, a new baby, or a major move. Others are finally settling into their dream home after years of hard work.

Whatever brought them to us, it's personal.

The last thing I want is for someone to pour their heart out in an inquiry form and receive a canned automated response or an AI-generated message that misses the humanity of the situation.

That's not the experience I want for my clients, and it's not the brand standard at The Organized House.

So while there are certainly parts of my business that can be automated, anything client-facing, especially at the top of the funnel, receives a thoughtful, personal response from a real person. For me, that's worth protecting.

Was hiring a virtual assistant worth it?

Absolutely.

Not because I suddenly got more hours in the day, but because I stopped carrying every single responsibility in my head.

Projects continue moving forward. Follow-ups happen more consistently. Details are less likely to get forgotten. And the business feels less dependent on me for every little thing.

That doesn't mean everything is perfect. It means there is more support, more structure, and more room for me to focus on the parts of the business that actually need me.

What other tasks are you willing to have your virtual assistant take on?

Quite honestly, there's very little I wouldn't trust Courteney with at this point.

Trust has never been the limiting factor. The bigger consideration is whether it makes sense for the business, the priorities we're focused on, and the margins we need to maintain.

There are several areas of the business that I could see Courteney becoming more involved in over time. Inventory management is one. Estimates are another. Both would help create additional consistency and take more responsibilities off my plate, but they also require time to build the right systems and processes before handing them off.

Social media is another area people often ask about. Could a virtual assistant help with content scheduling, engagement, and administrative social media tasks? Absolutely. But social media is its own strategy and requires its own investment of time and resources. At this stage, that's simply not where we're choosing to focus our efforts.

One thing I've learned is that delegation isn't about handing off everything you can. It's about handing off the right things at the right time. Just because someone is capable of taking on a responsibility doesn't automatically mean that's where the business will get the greatest return.