I meet business owners all the time who are considering hiring a Virtual Assistant (VA) for the first time. It can be scary, exciting, and a bit of a mess — especially if you don’t know what you’re doing.

I met Elysha when I first joined the Groove co-working app. We vibed immediately, having a similar approach to systems and productivity.

We had a chat a few months ago when I said something along the lines of, “There are a lot of people who hire VAs who aren’t ready to hire VAs.”

Sometimes, hiring a VA can be a knee-jerk reaction to overwhelm, or increased income, or a desire to offload the things you don’t want to do or don’t know how to do. But there are some things to consider before deciding to go from business-of-one to a team of two.

Elysha is a wealth of knowledge in this area, so I asked if she’d be willing to share her tips with Rebellious Systems subscribers. If you’re considering hiring a VA, this is an interview you wanna bookmark!

Table of Contents

1. When is the right time to hire a VA?

2. Tips for delegating

3. Advice for perfectionists wanting to hire a VA

4. Tips for communication

5. Managing working style differences

6. What if I’m scared of looking “too messy” to a VA?

7. First month tips with your new VA

8. Managing feedback with rejection sensitivity/anxiety

9. Red and green flags when hiring a VA

10. About Elysha

11. Work with Elysa/Open Tabs

What are some signs that a business owner might be ready to hire a VA, especially for those of us who tend to either overthink or rush into decisions? 

My guiding word for all things—especially in business—is notice. Noticing requires you to slow down, step away from the hustle, and be fully present. If you observe your life and business and see that you’re at capacity—where you can’t add anything else to your plate without tasks falling through the cracks or deliverables slipping—you’re likely ready for help.

Another sign is if you have goals you’re truly passionate about but realize, after honest reflection, that you can’t achieve them alone. This is a good indication that it’s time to bring someone on board.

For business owners who feel overwhelmed by the idea of delegating, what's your perspective on starting small vs. 'ripping off the bandaid?’

To me, this is actually a question about trust. If you’re overwhelmed by the idea of delegating, spend some time answering this question: What factors help you to gain trust in an individual? What factors make you lose trust? Once you know these things, and communicate them to your VA, you both can move forward in a way that honors your needs. If that means beginning with low-risk tasks—like creating a simple graphic or cleaning out your inbox—to test the waters, by all means, do so. If you’re truly swamped, “ripping off the band-aid” can be faster, but it still requires clarity on what success looks like.

Let's talk about the emotional aspects - how do you help clients work through perfectionism, control issues, or the fear that 'no one can do it quite like I do'?

This may seem harsh, but if you are bound by fear, perfectionism, or control and are not willing to do the work to break free from their influences, I would argue that you are not ready for a VA. 

To delegate is to release. 

To delegate is to trust. 

I’ll ask it again, what factors help you gain trust in an individual? What factors make you lose trust? What does “complete” look like for you? What is “good enough”? (And “good enough” doesn’t mean “subpar”—it just means that the deliverable has adequately met your needs.)

Are you truly willing to learn to grow in trust and confront your habits? If your answer is “I’m not sure,” then hold off working with a VA. Your need for control and perfection will only have a negative effect on your relationship with your new teammate. 

For those of us who struggle with clear communication or get overwhelmed by too much back-and-forth, what systems have you found work best for task delegation and feedback?

If there’s too much back-and-forth, sometimes the simplest solution is a quick 10-minute call to hash it out and move on. Voice notes are another effective tool—they allow you to articulate your thoughts with extra nuance and tone that’s often lost in written communication. But ultimately, this is a great opportunity for experimentation and finding what works best for you and your VA.

💡Note from Andrea: I use Voxer with a lot of my clients and it’s such a great asynchronous communication tool when you need to connect/hash things out quickly without scheduling a call.

How do you handle situations where a client's working style (like late-night work sessions or intense bursts of activity) differs from their VA's schedule?

At Open Tabs, our VAs work within a 9-to-5 schedule but upfront communication is still important when working styles don’t align. If you know you tend to send late-night emails or work in sprints, it’s important to address that early. A simple conversation like, “Hey, I’ll probably email you at 10 PM, but there’s no expectation for you to respond until your workday begins,” can make all the difference.

By being open and honest at the start—how you work, how they work, and what the expectations are—you set the tone for a smooth, respectful partnership. 

What's your advice for business owners who worry about seeming 'unprofessional' or 'too messy' when working with a VA?

Building is messy. There’s dust, half-finished pieces, and a lot of moving parts, and that’s okay. A good VA is skilled at bringing peace to chaos. They can step back, assess your world, and help bring order to the parts. So don’t worry too much about things being disjointed—that’s part of the process.

That said, this isn’t a pass to embrace total chaos. Before bringing on a VA, ask yourself: Do I know where I’m going? Do I have a clear vision for what I want to build? You don’t need everything figured out, but you should have direction. If you’re still throwing spaghetti at the wall, you may not be ready for a VA. You’re the captain of your ship, and your VA is there to support you, not navigate for you.

Can you walk us through what the first month typically looks like when working with a VA? 

The first month is all about laying the foundation. In Week 1, your VA will focus on getting access to systems, navigating logins, and gaining an understanding of your workflows. It’s a time for questions: What needs to get done? Where are you now? Where are you headed?

As you begin delegating tasks, expect plenty of back-and-forth to establish clarity. By the end of Month 1, you and your VA should start developing a shared language and rhythm, but this depends on how available and present you are as the leader. If you’re traveling or not accessible, progress may be slower since your VA needs your input to execute effectively.

During this time, your VA might also perform their own analysis of your operations, identifying opportunities to improve and streamline. The focus of Month 1 is understanding the gap between where things are now, where you want them to be, and starting to make small but meaningful changes.

The real momentum typically builds in Months 2 and 3, but the first month is where you establish the trust, structure, and clarity needed for success.

For those who experience rejection sensitivity or anxiety around feedback, how do you recommend handling situations where something isn't working out with a VA?

This starts with proactive communication. During onboarding, talk about how you and your VA prefer to give and receive feedback. Ask questions like, How do you like to handle bad news? How do you prefer we discuss challenges? These upfront conversations create a solid foundation for navigating difficult moments later.

If you’re already working with a VA and haven’t had this conversation, reflect on what you’ve observed in your interactions. Are they a straight shooter who handles direct feedback well? Or do they seem like someone who needs more time, context, and reassurance? Use those observations to guide how you approach the conversation. For someone who’s more sensitive, the sandwich method—starting and ending with positives while addressing the issue in the middle—may work well.

At the same time, be mindful of your own communication style. If you’re naturally more direct, ensure your tone creates a safe and supportive space for the conversation. It’s about balancing what you know about them with self-awareness, so feedback feels constructive and respectful.

What are some red and green flags business owners should look for when hiring a VA or agency?

When hiring a VA, one of the most important pillars to consider is communication. Pay attention to how they interact with you during the hiring process—it’s often a preview of how they’ll perform once onboard. If someone is slow to respond, lacks clarity, or seems disorganized, that’s a red flag. Transparency is just as important. If they withhold details, dodge questions, or seem hesitant to share processes, perhaps they may not be the right fit.

On the other hand, green flags include responsiveness, openness, and a willingness to answer your questions thoroughly and without irritation. Look for a VA or agency that creates space for your concerns and makes you feel seen and supported. Also, consider if their values align with yours.

Your gut is also a valuable tool. If something feels off during a discovery call, trust yourself and walk away. But if you sense warmth, professionalism, and a genuine ability to partner with you, that’s a strong green flag.

And of course, don’t overlook hard skills. Review their resume or experience to ensure their capabilities match your needs. For example, a VA’s skillset might differ from that of an office manager, so make sure their expertise aligns with the role. At Open Tabs, we vet all our VAs for communication, skills, and alignment to ensure they can meet your needs, but if you’re hiring independently, dig into these areas thoroughly before making a decision.

ABOUT ELYSHA: 

How’d you get started as a VA? What’s the story behind Open Tabs?

I got my start as a virtual assistant in 2007, thanks to a bit of family “voluntolding.” My mom had started a nonprofit, and as the most organized child, I was assigned to be her admin. Luckily, a family friend who owned a VA agency took me under her wing and taught me everything about virtual administration. I’ve been doing it in varying capacities ever since.

Open Tabs came to life in 2019 during a pivotal moment. At the time, I was working in fine dining and luxury hospitality. I hit a wall with burnout and realized I needed work that worked for me. That’s when I went all-in on virtual assistance. Now, Open Tabs offers a range of administrative services to authentic business leaders so everyone can live an unapologetically productive, ambitious, and restful life. We help leaders create sustainable administrative systems that free up their time and energy for high-impact duties. We plant our flag at the intersection of productivity and well-being because we believe that your journey to success is just as important as the destination.

The name itself? It came to me in a dream—something I’m grateful for since naming things isn’t my strong suit! Initially, I started as a solo VA but transitioned to an agency model to better serve my clients and grow sustainably.

How can people work with you? Anything else you’d like to plug/promote? 

If you’re ready for a high-performing VA who can help you reclaim time and bring clarity to your operations, we’d love to match you with someone from our team.

But if you’re not ready for a VA but could use more clarity and order in your business, a Spaghetti Session may be perfect for you. Consider me the Marie Kondo for your brain. In this 3-hour whiteboarding experience, we untangle all the ideas, tasks, and plans that have become like a knotted bowl of spaghetti in your mind. By the end of the session, everything is identified, labeled, categorized, and transformed into a detailed, actionable roadmap. This roadmap is so clear that you (or your VA) will know exactly what to execute, when to execute it, and which levers to pull right now in your business. 

If you’re interested in staying connected and exploring how to build your business with a holistic and mindful approach, I’d love for you to join my newsletter. Let’s stay in touch!