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The 5 Questions Every Business Owner Needs to Ask Before Hiring a Virtual Assistant

A virtual assistant can give you back hours of time per month–hours you can use to grow your business. Here’s how to find the right match. Whether you’re the founder of a start-up, a small business owner or an independent consultant, inevitably you wear all the hats. In fact, as founder of The Upside, I’ve […]

A virtual assistant can give you back hours of time per month–hours you can use to grow your business. Here’s how to find the right match.

Whether you’re the founder of a start-up, a small business owner or an independent consultant, inevitably you wear all the hats.

In fact, as founder of The Upside, I’ve been CEO, CMO, COO and CTO (just to name a few) since the initial launch of my business. Scarily, I was even my own lawyer at one point. 

But as a bootstrapped founder, I was so used to doing everything myself, that when The Upside finally had the revenue to support hiring additional help, I had trouble letting the work go, even though I absolutely needed to in order to have the bandwidth to scale my company.

Michelle Penczak of SquaredAway

Then, through the power of community networking, I met Michelle Penczak, the founder of SquaredAway which matches companies with remote virtual assistants with a wide range of skill sets.

What I didn’t expect was the impact this decision would have on my business, and the regret I felt by not making this move much earlier.  

We chit chatted about the huge need for more flexible and remote work for professionals who don’t fit inside the 9-5 box, and we bonded on our mutual mission of changing the way working works in America.

Michelle convinced me to let her match me with a virtual assistant who could alleviate some of the tasks that were weighing me down, particularly scheduling.

What I didn’t expect was the impact this decision would have on my business, and the regret I felt by not making this move much earlier.  

So I asked Michelle:

For business owners and consultants exploring the possibility of a virtual assistant, what are the 5 questions they need to consider in order to get the right match, and to achieve the results they seek?

1. What are the top 3 things I want to delegate immediately?

Often times consultants and business owners ease in to a virtual assistant by delegating their calendars, email inboxes and upcoming travel plans or low-priority business needs. Once there’s a comfort level and rhythm, you can build up and delegate more substantial tasks. 

2. What are the must-haves I need in an assistant?

Virtual assistants are not one-size-fits-all. In fact, they each have their own unique skill sets and backgrounds. Common skills include knowledge in specific software, relevant industry experience, a scheduling ninja or a background in marketing/paralegal studies/bookkeeping, etc. Understanding the skills that are a priority in your business will help you narrow down and match with the best assistant for your needs.

3. How much support am I seeking? Weekly, daily?

Getting a better understanding of the number of hours you’ll need per day, week or month will help you hone in on a virtual assistant that has the bandwidth and scalability that you need. Plus, virtual assistant matching services like SquaredAway typically have pricing plans based on set tranches of hours per month.  

4. What time zone works best for me?

Virtual assistants are located all over the United States as well as overseas. They work 100% remotely, so knowing ahead of time if a certain time zone is a priority or not will help eliminate time-difference headaches down the road.

5. What do I want to prioritize in my life so that my virtual assistant can help me reach that goal?

Understanding which areas are holding you back from having the time and freedom to reach your goals is critical. Figure out which tasks are taking up the most time, or giving you the biggest headaches, yet yielding the smallest ROI. The best virtual assistant relationships are the ones that eliminate time-sucking work so that you can re-purpose those hours to grow your business.

The virtual assistant Michelle matched me with has given me back hours of time each month that I was spending, unknowingly, doing back and forth communications and scheduling–time that I now spend growing my business and creating more revenue. 


Named Marine Corps Base Kaneohe Bay Military Spouse of the Year 2019, Michelle Penczak is a virtual assistant by trade and a military spouse by love. Her husband Sean is a pilot in the Marine Corps. Through multiple relocations and deployments, Michelle has built a vibrant, thriving independent virtual assistant business for herself over the past 5 years. Her own experience as a military spouse gives her unique insight into the multitude of challenges facing other military spouses who want to have a career of their own, but struggle to find gainful employment local to their latest duty station. SquaredAway’s pool of unique & talented personalities is where a significant amount of her assistants are chosen.

Erin Halper is the founder and CEO of The Upside, a platform that launches and grows independent consultancies for ambitious professionals redefining success beyond the 9-5. Since launching The Upside in 2017, Erin has advised more than 1,000 professionals on how to build a thriving consultancy, and has matched more than 100 businesses with consultants and freelancers in The Upside’s network.


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