The Trusty Oak Blog

How to Hire a Virtual Assistant: Your Guide to Outsourcing and Delegating Virtually

Girl raising her fist with excitement

For many entrepreneurs, getting help is a tall order. Hiring someone to take on part of your workload can feel like an impossible task, especially when you consider the cost, time commitment, and research it takes to go from solopreneur to entrepreneur with a team. 

Many solopreneurs turn to hiring a virtual assistant as their first team member for a few reasons. First, hiring someone on a fractional basis can right-size the cost of building your team; instead of hiring an employee, you can get help with just the specific tasks you’d like to delegate and scale up as your company grows. You only pay for deliverables with a fractional freelance virtual assistant, rather than paying a salary while your company is still in the early growth phases. 

Second, virtual assistants expand your talent pool. You can hire a virtual assistant from nearly anywhere, although we recommend sticking with a VA based in your country to minimize time difference issues and simplify communication. A virtual assistant doesn’t have to be based in your city or even time zone, giving you a bigger pool of talent to search. 

“My VA has done more for me in 20 hours of work than I’ve done in probably a year of just making things up on my own. That’s not a sales pitch, infomercial, or me being paid to say what I’m saying. It’s true. I’ve gotten a business card designed, a logo designed, website updated, streamlined for SEO, content written, colors and fonts changed, things I would have never thought about if I was doing this on my own.”

Dave Bahr, CEO, In-Sightful Living

Finally, hiring a virtual assistant works uniquely well with the challenges faced by a fledgling company. Virtual assistants and their work is adaptable and scalable, ready to change as your business needs grow and expand.

Rather than hiring an employee with a job description and a static list of tasks, entrepreneurs turn to virtual assistants for the flexibility emerging companies demand. Because virtual assistants typically work as contractors, their work is highly adaptable and can change as needed to support your company. 

What Can a Virtual Assistant Do?

Virtual assistants can perform a range of tasks. When thinking about hiring a virtual assistant, you want to look at repetitive, recurring tasks you can hand off to get the most bang for your buck.

Common tasks virtual assistants complete for small businesses include: 

  • Calendar and schedule management
  • Inbox management
  • Customer/client communication 
  • Research and data gathering
  • Invoicing
  • Consolidating and organizing files 
  • Improving automation, workflows, and tech solutions for business processes
  • Social media management
  • Content creation and management
  • Blogging and writing
  • Email marketing 

There’s more a virtual assistant can do – especially on the personal or executive assistant level – but this list is a good place to get your mind working about what you could start handing off to a virtual assistant. 

Related: Virtual Assistants Help Small Businesses Scale: 7 Reasons to Hire a VA

How Do You Hire a Virtual Assistant?

1. Decide what you want to delegate

First, it’s important to decide what it is you want to delegate. For some entrepreneurs, the challenge will be narrowing down tasks from a long list, prioritizing what should be done first. For others, it may be difficult to come up with even a few tasks if you’re used to handling everything on your own and hesitant to bring on a new team member. 

You can use a delegation matrix to help get the creative juices flowing here. We’ve developed a free one that’s easy to use. 

Delegation Matrix from Trusty Oak

Download Your Free Delegation Matrix

Other ways to decide what to delegate include: 

  • Review your typical daily to-do list and divide it into three columns. Ask yourself what you’d like to start, stop, and keep doing, making a column for each list of tasks: start, stop, and keep. Tasks you’d like to stop doing could be good ones to delegate, leaving more room for you to keep and start doing tasks you’d like to prioritize. 
  • Read through sample job descriptions online to see what typical administrative, marketing, or executive assistants do for entrepreneurs. This may spark some ideas for you. 
  • Talk to someone in the virtual assistant business or lean on your network. Many virtual assistants or virtual assistant companies offer free consultations where they can explore the ways your needs and their services dovetail. 

2. Write it out and be descriptive

While searching for a virtual assistant is a little different than searching for a traditional employee, it’s still helpful to create a job description or at least a document that goes into some detail about what you’ve decided to delegate and how. 

Answer these questions to get your job description started: 

  • What tasks will you be delegating? 
  • What frequency will these tasks need to be completed at – daily? Weekly? Monthly? As-needed? 
  • What requirements – including past experience, education, or certifications – are necessary for this role? 
  • How many hours per week do you anticipate these tasks will take? 

This pre-work will be helpful in the next stage when you start sourcing and reviewing potential candidates.

3. Post your job or find a company

Next, you’ll want to take one of two routes. In the first route, you’ll take your notes, craft it into a job description, and publish it. You’ll need to then receive applications, vet applicants, conduct interviews, and make a hiring decision. Remember, this process is often drawn out, and you’ll want to be careful how you approach each step along the way. 

“My VA creates marketing campaigns, develops my marketing collateral, and coordinates my social media marketing activities. I have seen an increase in traffic to my website and increased market presence. I attribute this to their knowledgeable and dedicated team of Virtual Assistants that are now part of my team.”

Scholley Bubenik, CEO and Founder, Premier HR Solutions

Alternatively, you can go through a virtual assistant company that does this part of the process for you. If you opt for this route, choose a company with a highly effective vetting and hiring system and a transparent matching process. A company can take the guesswork out of hiring a virtual assistant by providing the candidates directly to you. 

Related: Browse our vetted and experienced virtual assistants’ profiles

4. Give your new VA feedback and set them up for success

Finally, once you’ve started with your new virtual assistant, it’s crucial to actively engage in an onboarding process with them. Expect the first few weeks and even months of your relationship with your virtual assistant to include lots of trial and some error. Your leadership in the process of getting your virtual assistant up to speed will be vital to the success of the relationship. 

Give your virtual assistant consistent, honest, and constructive feedback as they learn your desired workstyle and how to do necessary tasks. You can use screen-recording services like Loom to document tasks and teach your VA to do things, as well as project-management software like Trello or Asana to keep track of your progress on bigger initiatives. Give your VA time to get to know you and your business and focus on building rapport and relationship while giving actionable feedback and direction. 

Some virtual assistant companies help make this onboarding process simpler with client support representatives, onboarding support, and consultations. Either way, your first several weeks with a virtual assistant will require your active participation to get the results you want as you delegate and handoff tasks. 

If you’re feeling ready to hand off tasks and get more productive with a virtual assistant, you can get matched with a Trusty Oak virtual assistant by signing up today! 


Amber Gray

Amber Gray is the founder and CEO of Trusty Oak, an Austin-based virtual assistant company providing administrative and marketing support to small business leaders, authors, and creative teams. A people-first approach to hiring, along with a scalable growth model have positioned Trusty Oak as a flexible, dependable, and affordable alternative to hiring administrative and marketing employees. In 2021 and 2022, Trusty Oak was named Freelancer Hiring Platform of the Year, and in 2021 Amber was recognized as Austin Business Woman of the Year.

Before founding Trusty Oak, Amber spent five years at a rapidly growing digital agency based in Austin, TX. Four of those years, she was responsible for hiring and leading both local and virtual teams while working closely with clients ranging from CEOs to bestselling authors to build their brand online. As VP of Operations, Amber helped lead the company’s growth to #15 on Austin Business Journal’s Fast50 List in 2014.

As a female founder and leader of a company that has quickly established a recognizably special culture within a non-traditional workforce, Amber has energized and empowered women from diverse professional and personal backgrounds to go against the grain of historically standard female roles in business, technology, and leadership. Trusty Oak provides an opportunity for experienced admin and marketing professionals to work independently as freelancers, but with a supportive internal network consisting of other ambitious and resourceful remote workers.