When I speak with entrepreneurs who have hired assistants through our company, WorkBetterNow, the response is often similar to that of our client, Mark Hunter:  

“Best move ever…my only regret is not doing it much sooner.” 

It's music to my ears when busy professionals get the support they need.  

Too often, though, by the time business owners come to the realization that they need an assistant and finally decide to take action – they’ve already hit a breaking point. 

That can lead to rushed decisions: hiring whoever happens to be available, choosing the cheapest hourly rate, or clicking on the first search result for “virtual assistant.” Unfortunately, those choices rarely lead to lasting success. 

The truth is, hiring the right virtual assistant (VA) can be transformative. But it takes intention – and the right hiring approach – to get there. 

Based on my experience overseeing the placement of thousands of assistants – here is what I would suggest a small or midsize business owner should consider before hiring a VA.  

1. Are You Looking for a Task-taker or a True Team Member? 

There’s a big difference between hiring someone to knock out a to-do list and bringing on a professional who contributes to your business’s long-term success. 

Many virtual assistants work part-time across multiple clients, which can limit their availability and focus. If you’re serious about offloading real responsibilities, look for a full-time, dedicated team member. 

When evaluating a hiring partner or agency, ask how their candidates are placed: Are they part-time? Full-time? Do they work for multiple clients?  

The best partners will help you find someone who’s fully committed to your business and invested in your goals. 

2. Do You Know What Success Looks Like for This Role? 

Hiring a VA without a clear vision is a common (and costly) mistake. You don’t need to have every task mapped out – but you do need clarity on outcomes. Are you trying to free up 16 hours a week? Improve customer response times? Get out of your inbox? 

A good staffing partner will work with you to define success and match you with someone equipped to deliver it. Look for virtual assistant firms that help you think strategically – not just send over resumes and scatter interview invites all over your calendar. 

At WorkBetterNow, when a client doesn’t already have a job description, our expert team helps them develop one. By defining success from the outset, you’ll set yourself up for a more aligned match and greater long-term success.  

3. Are You Hiring for Both Skills and Fit? 

It’s easy to find someone who knows how to manage a calendar or run reports. But the real make-or-break factor is cultural fit: communication style, problem-solving approach, reliability, and initiative. 

Ask any potential hiring partner about how they assess soft skills and long-term fit. Do they screen for English fluency? Do they evaluate professionalism and mindset, or just technical abilities? Do they help you find someone who aligns with your values – not just your tasks? 

The best providers understand that successful hires go beyond hard skills – they ensure your assistant can grow with your team. 

4. What Is the Expected ROI of This Hire? 

When hiring a virtual assistant, it’s easy to get fixated on hourly rates or monthly fees. But smart business owners focus on outcomes, not just expenses. 

Ask yourself: 

• What will this hire allow me to stop doing? 

• How much more could I focus on high-impact work with the right support? 

• What kind of growth or cost-savings could this unlock for my business over time? 

That’s your real ROI. 

The right VA can increase the time you spend on what Strategic Coach® calls your Unique Ability®, improve your client experience, speed up operations, and reduce your mental load. But those returns only happen if you hire someone capable of delivering at a high level – and if the hiring process is structured for long-term success. 

5. Do You Want to Partner with a Firm or Hire Directly? 

One of the key decisions you'll face is whether to hire a VA directly or partner with a firm. 

Hiring directly gives you full control—from sourcing and interviewing to onboarding and management. This can work well if you have the time, resources, and systems in place. However, it also means taking on all the risk and legwork yourself. 

On the other hand, partnering with a firm can streamline the process. A good firm will handle vetting, ensure a strong talent match, and provide ongoing support—so you’re not starting from scratch or relying on guesswork. 

Working with a talent firm simplifies the process. A good partner will pre-vet candidates, help you onboard smoothly, and offer ongoing support and replacement support if needed. That way, you're not just getting a person – you're getting a system that sets them (and you) up to succeed. 

And while some may assume talent firms are more expensive, they often save you money in the long run by reducing hiring time, minimizing risk, and ensuring a better fit from the start.  

Take Action to Move Your Business Forward  

The best move you can make is to take action. While many entrepreneurs wait too long to hire a virtual assistant, you can jump ahead of the pack by taking the first step.  

Consider WorkBetterNow as you begin your research process. As an Employer of Choice in Latin America, we receive 4,000 applications per month – and accept only the top 2%. This means we are able to provide you with top-tier talent at a fraction of the cost.  

Getting started is easy. Book a demo here, and you could have a WorkBetterNow Certified Professional™ on your team in as little as two weeks.  

Soon, you’ll be able to get more tasks off your plate, get your time back, and have the energy and focus to drive your business forward.  

WorkBetterNow (WBN) provides outstanding remote talent to small and midsize businesses. WBN’s highly skilled and pre-vetted Latin American professionals are hand-matched for each client’s unique needs. Hundreds of growing businesses turn to WBN to unleash their potential through our exceptional talent, ease of hiring, and ongoing support. Request a consult today!