How to Hire a Virtual Assistant Who Actually Works Out

Virtual assistants (VA’s) can be invaluable to business owners and executives who are overwhelmed with managing jam packed calendars, processing 100+ emails per day, responding to phone calls and Slack messages, and handling many of the administrative tasks required to run their business.

However, the vast majority of founders and executives seeking a VA can’t find one that’s good enough to truly take these tasks off their plate.

We’ve been in the business of hiring virtual assistants (VAs)—specifically full time executive assistant VAs—for over 3 years. And there are a number of common scenarios that we’ve seen (and continue to see) play out:

  • The need to train or micromanage their VA takes more time and effort than it’s worth.
  • The VA is good for the first week or month and then they start dropping the ball.
  • The VA isn’t organized, responsible, or reliable enough to do the job well.

These experiences stem from 3 core problems with the typical approach to VA hiring:

  1. People don’t get specific enough about what they need their VA to do.
  2. People hire VAs from the wrong places (like Upwork and Fiverr).
  3. People don’t vet VA candidates rigorously enough.

In this article, we’ll explain each of these problems and how you can solve them. We’ll also include examples of job description responsibilities, structured interview and reference check questions, and work sample test ideas that can help you vet candidates more effectively.

Lastly, we’ll share how our executive assistant service can help you shortcut the hiring process and get a world-class VA.

Note: This post is tailored for entrepreneurs and executives looking for talented, reliable VA’s that can stick with you for a long term engagement. But regardless of the type of VA you’re looking for, this article will provide you with valuable insight to find the right VA for you. 

If you’ve been wanting an assistant but haven’t had the time to hire one, or have had bad experiences with your first virtual assistant, click here to get started. You can try an assistant for a month or two and see how you like it. For testimonials from our clients, check out our homepage.

Problem #1: People Don’t Get Specific About What They Need Their Virtual Assistant to Do

Out of all the clients we work with, fewer than 5% of them come to us with a detailed, well thought-out list of responsibilities that they’d like their VA to execute.

Most of the time people who want to hire VAs are just drowning in tasks, and someone—a friend, colleague, board member, etc.—tells them they should get an assistant. 

They have a vague idea of how VAs can help with things like email and scheduling and other administrative tasks. But that’s the extent to which they’ve thought it through.

By the time they go to write a job description, they end up copying and pasting the text of a generic VA job post they found through Google because they haven’t defined their own specific needs. And there are several problems with this.

First, what awesome candidate is going to apply to a generic job post? If you want quality applicants, you need to create a specific and compelling job description.

Second, if you want to find a VA that’s a good fit—which is the only way they’ll be truly useful and worth hiring—how are you supposed to do that if you haven’t gotten specific about the skills they’ll need?

If you need someone to coordinate office birthdays and order lunch, that’s one thing. But if you need someone to coordinate the calendars of 7 team members, or reply to emails on your behalf, or help build pitch decks and powerpoint slides, you’ll need to screen for candidates who can handle these kinds of tasks with confidence. 

Scoping what you need is a nontrivial step that’s essential to your success in hiring.

How To Get Clear About What You Outsource To An Assistant

The easiest way to approach this is to do a calendar analysis to figure out:

  • What are the specific tasks and categories of tasks that you spend your time on each month?
  • How much time are you spending on each of them?
  • What proportion of time are you spending on your core competencies versus everything else?
  • Which time-consuming or repetitive tasks could you be delegated to an assistant?

Create a list of potential to-do’s for your VA and figure out your “must-haves” versus your “nice-to-haves”.

In addition, most founders and executives have a list of tasks they wish they could do or forever “plan” to do that they never actually have time to do. For example, clients have told us they wish they had more time for things like:

  • Sending birthday cards to friends.
  • Sending follow up notes (or thank you notes) to customers and clients.
  • Organizing events for their company or customers.

Items like these are also worth adding to your list. You don’t need to overcomplicate this analysis, but the more thorough you are, the better chances you’ll ultimately have of finding the right VA. 

Synthesizing Your Needs Into Specific Responsibilities for Your Virtual Assistant Job Description

Once you’ve refined your list of needs, you need to translate that into responsibilities that you’ll put in your job description.

Here’s an example of how to do this well (from a Netflix executive assistant role on LinkedIn):

  • Maintaining high volume, complex calendars for a growing team of Netflix HR professionals, including scheduling internal and external meetings with multiple parties across multiple time zones.
  • Coordinating various HR-focused projects. Examples include: Creating and/or editing slide decks and broad communications, creating and/or analyzing HRIS reports, assisting with team learning sessions, and organizing working groups.
  • Managing general administrative duties, including processing expense reports and facilitating team and visitor requests.
  • Team event planning and facilitation including offsites, social hours, and training sessions.
  • Managing travel arrangements (domestic and international).
  • Taking notes in meetings and circulating information to the greater HR team.

This is what getting specific looks like. This is how you can get applicants who are the right fit.

Note: There are a lot of misconceptions about what a VA can and can’t do for you. Some people have unrealistic expectations about what a VA can do, while many underestimate what a great VA is capable of. If you’re considering hiring a VA, read our founding story for a better understanding of the VA market, including what average VA’s can typically do versus what the absolute best VA’s can do.

Problem #2: People Hire VA’s from the Wrong Places (Like Upwork and Fiverr)

Many employers have an oversimplified approach to choosing the job board they’ll post on. Typically, the thinking is if you want to hire a US-based VA, you use LinkedIn. If you want to hire an international VA, you use a freelancer site like Upwork or Fiverr. 

We generally advise against using sites like Upwork and Fiverr. Even if you want an assistant for very basic admin tasks, such as spreadsheet data entry, it’s often challenging to find one who’s reliable. It’s not uncommon to waste time trying to interview or meet with them and then get ghosted or flaked on.

The other issue is that freelancers who get noticed on these sites tend to be the most expensive and have the least time and attention to give to new clients.

This is the catch-22 of “marketplace” platforms: Newcomers who might be cheap and ready to dedicate themselves to you full-time are impossible to identify, while those who get lots of gigs and ratings and look compelling are the most shrewdly ambitious freelancers who are typically already fully booked up and charge the highest prices.

How to Choose the Right Job Boards

In reality, there are far more job boards to choose from, and the right job board for you depends on the market or markets in which you’re looking (or open) to hiring a VA from. 

LinkedIn generally works well when hiring domestic VAs and international VAs from some countries. 

But if you want to hire someone from Indonesia, Malaysia, or the Philippines, you have a problem: VAs from those regions don’t typically use LinkedIn. They’re found on job boards that most US employers have never heard of, such as JobStreet and Kalibrr

So, if you want the advantage of hiring VAs at more affordable rates in other countries, you need to post on the job boards that are specific to those countries or regions to find good candidates.

The Importance of Running Paid or “Pro” Job Posts

Once you choose a job board, it’s also essential to run paid or premium posts. If you try to rely on free posts, it’s unlikely you’ll get the volume or quality of applicants that you need to find the right hire. 

Pricing and features for premium posts vary depending on the job platform, but this explanation of LinkedIn’s pricing provides a good overview of the advantages and fee structures of “pro” posts.

Problem #3: People Don’t Vet VA’s Rigorously Enough

Consider the standard process that’s used when hiring for generalist roles like an assistant. It starts with reviewing superficial indicators to determine applicant quality, such as:

  • How their profile looks.
  • Where they went to school.
  • Which companies they’ve worked for.
  • How long they worked there.
  • The positions they’ve held.
  • Their years of experience.

Then, from these criteria, which provide very little concrete detail about candidates’ actual capabilities, people choose the ones who look the best on paper to interview. After a few Skype or Zoom video calls with several of the best looking candidates, they’ll make a decision—usually based on who made the best first impression (hint: it’s usually the extroverts).

Notice what’s wrong here. The typical hiring process:

  • Doesn’t measure problem solving ability: How smart they are, how quickly they respond and adapt to new situations, etc.
  • Doesn’t measure communication ability: How well they write and communicate on your behalf or alongside you with key people (team, board members, investors, etc.).
  • Doesn’t measure key character and behavioral traits: Organization skills, detail-oriented skills, reliability, etc.

And yet, these are the generalist skills and traits that determine the quality of a VA.

If you want to make the right hire, you need to evaluate candidates on these in your interviewing and vetting process.

How to Vet Applicants on the Skills and Traits That Predict Good On-the-Job Performance

There are 3 main tools that you have to evaluate candidates on the skills and traits that matter:

  1. Structured interviews
  2. Work sample tests
  3. Reference checks

Below, we’ll explain how to approach each, including mistakes to avoid and best practices based on the processes we use when hiring VA’s for our executive assistant service.

#1: Structured Interviews

When done correctly, the interview process can be used to evaluate candidates’ verbal communication skills, behavioral traits, and even problem solving ability. 

But the extent to which you evaluate these qualities depends on the questions you ask

Most people ask generic questions that come to mind when glancing at a candidate’s resume. At best, this provides a vague assessment of their verbal communication skills and personality.

Employers also tend to ask different questions to different candidates (known as unstructured interviews), giving them no way of comparing the answers of candidates. When they have two or more applicants who spoke really well, it’s not clear how to tell who is actually better for the role.

Instead, the best practice is to: 

  1. Use structured interviews that ask an identical set of questions to everybody so that you can cross compare the answers of each candidate. 
  2. Ask questions that are designed to assess candidates on the key qualities that great VAs have.

Here are some examples of structured interview questions for a VA that help you assess them on the qualities that matter:

  • Think of the people who know you best—friends, family, colleagues. What would they say are your greatest strengths when it comes to 1) working with people and 2) accomplishing your goals?
  • What would they say are your greatest weaknesses in each of these areas?
  • Tell me about the hardest problem you’ve ever solved at work and how you solved it.
  • What does it mean for someone to be an effective communicator in a work context? Describe what that looks like in action.
  • Tell me about your worst experience dealing with customers or colleagues at work. What made it so bad and what would you have done differently, if anything?
  • Working means sacrificing time and energy. What are the top things that motivate you most to make those sacrifices? Explain why.
  • In terms of skills and experience, what do you think are your strongest areas for taking on this role? Your weakest areas?
  • Imagine that you accept this opportunity. In a year from now, things don’t work out and we’re no longer working together. Why did things end?
  • How do you see your career and how does this position fit into the picture of the career you imagine for yourself?

#2: Work Sample Tests

Work sample tests are a key component to ensuring you hire a VA that’s capable of doing the jobs you need them to do. Many people skip this step, getting their VAs first work samples after they’ve already onboarded them—during the first few weeks on the job—only to discover that the person isn’t up to par with what they need.

When done correctly, work sample tests are an invaluable addition to the hiring process because they allow you to challenge candidates and see their work before you commit to hiring them. 

Here’s how you can approach this:

  • Step 1: Look at the list of must-have items you identified you want your VA to do.
  • Step 2: Identify items that most easily translate into a deliverable project.
  • Step 3: Choose at least 3 of them and have candidates do at least a day’s worth of deliverables for you.

To demonstrate how this can be done, here are some work sample test ideas you could use or draw inspiration from. Within each, there are opportunities to gain insights into candidates’ communication, behavioral traits, and problem solving abilities.

Idea #1: Composing Emails

Give them 5 email scenarios indicative of the types of emails they’d be expected to handle in the role, and have them write their responses. 

This allows you to see their writing ability and email etiquette. Depending on the scenarios, you can also gain insights into their personality and problem solving ability. 

Idea #2: Planning a Travel Itinerary

Have them create an itinerary for a fake trip, complete with a price breakdown. And have them write out the steps they took to come up with it.

This can give you insight into key behavioral traits like their organization skills and how detail-oriented they are, as well how they approach solving the problem of planning a fake trip for someone else. 

Idea #3: B2B Lead Generation

Have them look at your company, understand your product or service, and create a lead list of 20 companies that you should be trying to sell to. Then have them write out the steps they took to come up with it.

This may not be the type of job you’re hiring a VA for, but it’s an example of an exercise that can provide insight into their problem solving ability and thought process for approaching a task they may have never done before.

#3: Reference Checks

Doing reference checks has become less common for 2 core reasons: 

  1. Many companies have policies to never share opinions about past employees to avoid the risk of defamation lawsuits, so they’ll only confirm or deny dates of employment.
  2. Candidates tend to only list people who they know will say favorable things about them.

However, doing reference checks is still valuable because when you hear negative things from past employers about performance, you can be almost certain that you’re going to experience the same issues. A short call has a decent chance of sparing you a mis-hire.

The key to doing reference checks well is to give applicants less latitude about who they can provide as a reference. For example, in our hiring process, we require applicants to share the direct supervisors of their last 3 listed positions on their resume. It’s not a perfect solution, but it will yield better references more of the time.

Then there’s the art of doing reference check calls. If you don’t ask the right questions, you won’t get relevant or useful information about the candidate. 

Here are some examples of structured questions for references or referrals:

  • In what capacity were you associated with the candidate?
  • What were the candidate’s roles and responsibilities?
  • What was it like to work with or supervise the candidate?
  • Can you describe the candidate’s strengths in the role and in working with the company?
  • Can you describe their weaknesses and areas of needed improvement? 
  • What type of work environment do you think the candidate would be most likely to thrive in, and why?
  • Did the candidate have any major accomplishments while working for you? If yes, what were these?
  • Could you recall why the candidate resigned?
  • We are considering the candidate for the Executive Assistant position. Success for this role would mean being able to assist the C-level executive with whatever tasks they need help with. How well do you think the candidate would do in this role? Do you think the candidate is suitable for this role?
  • If given the chance, would you want to work with the candidate again? If no, why not?
  • Is there anything else you would like to add?
  • Is there anyone else I should speak to about the candidate who can provide further insight about their performance and working style?

Note: Once you’ve chosen who you’d like to hire, your job’s not over. The next step is to go through the onboarding process which involves negotiating their hourly rate, signing contracts, doing compliance, and setting up payments. We won’t go deep into this here, but do your due diligence during this step to avoid any potential legal issues (especially if you hire in another state or in international markets). 

How to Shortcut the Hiring Process and Get a World-Class VA

If you’re a founder or executive who wants an effective, reliable VA that can manage a high volume of tasks for you, the hiring process can take weeks or months to execute correctly.

By following the process we’ve laid out above, you will significantly increase the chances of finding the right hire. But many people in this position simply don’t have time for this. They’re drowning in overwhelm, and they needed help yesterday.

These are the people we created Persona to help. We’ve developed an in-depth process to find the best virtual assistants in the world—hiring roughly 1 out of every 1,000 applicants. 

Our assistants can execute essentials like email and calendar management, research, and data entry. But in many cases they also help clients with things like:

  • Social media management
  • Workflow and project management
  • Bookkeeping
  • Payroll
  • Customer support
  • Employee onboarding
  • Presentations
  • eCommerce management (on platforms like Amazon)
  • Personal assistant tasks like booking dinner reservations or scheduling grocery deliveries

Due to the rigor of our hiring process, which focuses on assessing candidates on the big 3 qualities we’ve discussed throughout this post, Persona assistants are able to manage these types of tasks with a higher level of reliability and competence than what most virtual assistant companies can offer. 

We help a wide range of people from small business owners, to executives at large companies, to former employees of tech giants like Google, LinkedIn, and Uber. 

How Our Service Works

We’ve made the process for getting a world-class assistant simple.

Here’s how to get started with us: 

  • Step 1: Complete our form to let us know your needs
  • Step 2: If you’re a good fit, we’ll set up a call to discuss our service with you.
  • Step 3: Our team will hand pick an assistant who we think will be a great fit for you based on your needs.
  • Step 4: Our talent team will guide you through the onboarding process over 2-3 weeks.
  • Step 5: For a flat monthly rate, you get a fully dedicated assistant working for you 40 hours per week (no long-term commitment needed).

If you’ve been wanting an assistant but haven’t had the time to hire one, or have had bad experiences like the ones I’ve described in this post, click here to get started. You can try an assistant for a month or two and see how you like it. For testimonials from our clients, check out our homepage.

One final note on virtual assistants:

Most virtual assistants (outside of specialized virtual assistants) are only capable of simple, rote tasks like data entry. If you really want a general virtual assistant who can work alongside you on your most important daily tasks, it’s imperative you focus on hiring the right virtual assistant. While you may think that hiring a virtual assistant is easy compared to hiring for a technical role, it’s actually much harder. Soft skills are what separate the truly great virtual assistants from the rest, and most virtual assistant services have no way of vetting these critical skills.

This is why most people need to hire many virtual assistants before they find the right fit. But this is a huge time commitment, and it can take a dozen or more trials until you find the right person. Just imagine how much time finding the right VA this way can cost you.  

Virtual assistants work on tasks that are too important and impactful (like email management, scheduling, calendar management, etc.). You can’t entrust your inbox to someone who is unskilled or disorganized. If you don’t use Persona, find a virtual assistant service that focuses on finding each client a truly great general virtual assistant (stay away from services offering a specialized virtual assistant), and don’t be surprised if the virtual assistant cost is more than what you expected. After all, you’re hiring your right hand person, and they’re going to be in your calendar, your inbox, your project management tools. They’ll have full insight into your work life and, if they’re good, they can double your productivity. But if they’re bad, you would have been much better off without one. Choose wisely.


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