Virtual Assistants for Entrepreneurs: Are They Worth It?

In the best case scenario, hiring a virtual assistant (VA) can be absolutely transformative for your business. 

Instead of spending a good portion of your work weeks on necessary but relatively low impact things (e.g. scheduling meetings, organizing emails, fixing SEO issues on your website, responding to comments on social media, etc.), you can spend more time on things that actually move the needle forward for your business: product development, business development, optimizing company workflows, fundraising, etc.

And while you’re at it, you can have a better work-life balance. You can focus on the work that matters and have more time to enjoy your life.

When you find the right person—someone who is highly competent, trustworthy, and possesses the right set of skills and traits—this is all possible and worth the investment.

However, finding a highly competent VA that’s going to transform your working life turns out to be a lot more challenging than you might think. In fact, many entrepreneurs who hire VAs end up disappointed for one reason or another—the VA was flakey, they weren’t that organized, they couldn’t hit deadlines, the quality of their work wasn’t good enough…the list goes on. 

In this article, we’re going to discuss why this is and explain how our remote executive assistant service solves these problems. Specifically, we’ll cover:

  • Why the talent-level of your VA will determine whether hiring one is worth it or not
  • 4 essential qualities to look for when hiring VAs
  • The challenges of finding and hiring great VAs
  • The hiring methodology we’ve developed to find world-class virtual executive assistants
  • How our remote executive assistant service works

If you’ve been wanting an assistant but haven’t had the time to hire one, click here to get started. You can try an assistant for a month or two and see how you like it. We require no long-term commitments. For testimonials from our clients, check out our homepage.

When You Hire a VA, Hiring for Talent Determines Whether Your Investment Is Worth It or Not

Before we get into the challenges of hiring VAs—whether on your own or through a service—we need to first discuss why the talent of your VA matters.

It’s easy to dismiss the need for having a super smart and competent VA because a lot of what entrepreneurs want to delegate can seem relatively straightforward. 

For example, a lot of business owners that we speak with want their VA to help them with basic administrative tasks like email and calendar management. And, on the surface, this seems like something that just about anyone can do. We all manage our own schedules and inboxes, so is it really necessary to have a high standard when hiring for this position? 

This perspective is understandable yet it doesn’t take into account the nuance that’s often involved in things like email and scheduling. Things that may seem obvious or basic to us actually require a great deal of judgment and sophistication for an outsider to complete. 

For example, to process email on an executive’s behalf, assistants need to have a deep understanding of things like:

  • Which emails are absolutely urgent and essential, requiring your immediate response?
  • Which emails would it be appropriate for them to respond to on your behalf? (And how capable are they of responding in a personable and professional way?)
  • Which emails can be deleted or ignored?
  • Which can be addressed later?

These types of preferences are essential for an assistant to learn quickly. And equally important preferences apply to scheduling as well. For example:

  • When a scheduling conflict comes up, which meetings and events take priority over others?
  • Which meetings need to be rescheduled by you personally (e.g. for the sake of an important or delicate relationship)? 
  • Which meetings would it be appropriate for them to reschedule on your behalf?

There are a lot of microdecisions that assistants need to make that may seem trivial to you but in fact aren’t trivial at all. Email and scheduling are often at the core of essential business relationships and decisions. If a crucial email is archived and goes unresponded to, or a poorly handled scheduling conflict harms an important relationship—these things can have significant adverse effects on your business.

If you’re going to entrust an assistant to help you manage these things, you need to ensure they have the qualities and traits necessary to learn how to navigate these situations appropriately.

4 Essential Qualities to Look for When Hiring a VA

Over the last 4 years building our remote executive assistant service, we’ve learned that there are 4 qualities that determine whether someone will be successful and effective in a VA role:

  1. Problem Solving Ability: How smart are they? Can they figure things out in new and complex situations? 
  2. Key Character and Behavioral Traits: Are they organized, reliable, trustworthy, detail-oriented, etc.?
  3. Communication Ability: How well do they write and communicate? Can they communicate on your behalf or alongside you with key stakeholders (executive team members, board members, investors, etc.)? 
  4. Tech Savvy-ness: How comfortable are they with learning new technologies and software? How quickly can they pick up and learn the programs that modern companies use to run their businesses?

Through our experience vetting hundreds of thousands of applicants, we’ve learned that people who possess these 4 qualities make world-class assistants. Not only can they quickly learn how to navigate the nuanced scenarios of calendar and email management like we discussed above, but they can manage a wide range of other tasks competently as well. 

The beauty of hiring assistants with these qualities is that you can ask them to handle tasks without providing much direction—even if it’s something they’ve never done before—and they can figure out how to do it. In addition, they can also take on more complex projects that are outside of what you might find in traditional virtual assistant services.

For example, by thoroughly vetting applicants based on these qualities, assistants in our virtual executive assistant service help our clients with things like improving internal business processes, running social media marketing campaigns, project managing new company programs, and more. 

Below, we’ll expand on our hiring methodology and the types of work our assistants execute for our clients. But before we do, let’s discuss the challenges with finding VAs that actually possess all of these essential qualities. 

The Challenges to Hiring Great Virtual Assistants

There are 2 common paths to hiring a VA:

  1. Hire one yourself via a freelance marketplace like Upwork.
  2. Hire one through a virtual assistant service.

Both of these paths have issues that often lead to poor outcomes for entrepreneurs. We’ve written at length about them in previous articles, so here we’ll summarize and link to those pieces for further detail.

Hiring VAs Yourself via Freelance Marketplaces

It’s super common for founders to think, “I need a VA. I’ll just hire one on Upwork.” This might work if you want a part-time person to do some basic spreadsheet data entry (or some other rote administrative assistant task that doesn’t require much skill). 

But if you’re hoping to hire someone who you can form a long-term relationship with and who can manage a wide range of tasks for you—and certainly if you’d like the ability to entrust your VA with more nuanced responsibilities and projects—it’s very difficult to find this level of talent on sites like Upwork or Fiverr. 

The VAs with good ratings are typically booked up with little room in their schedule to take on new clients. And identifying VAs in the rest of the pack who would actually be reliable and good is nearly impossible. 

As a result, hiring VAs via these marketplaces tends not to work out well for most businesses. If you want to hire a VA yourself, check out our article on how to hire a virtual assistant who actually works out.

We expand on these issues and discuss best practices we’ve learned such as running paid or “pro” job posts on LinkedIn, or using regional job boards if you want to hire VAs from other countries (e.g. from Brazil, Colombia, Malaysia, or the Philippines).

We also share tactics for vetting applicants on the skills and traits that predict good on-the-job performance, including examples of effective interview questions and work sample tests you can use.

Hiring a great VA for your own business is time-consuming and a lot of work to do right. This is why we started Persona—to help busy entrepreneurs shortcut this process. We’ll explain how our service works in a moment. 

First, let’s cover the second common path to hiring VAs: hiring them through virtual assistant companies.

Hiring VAs Through Virtual Assistant Services

There’s a growing number of companies offering virtual assistant services for entrepreneurs. However, as far as we can tell, most of them do not have thorough hiring processes for vetting applicants based on the essential qualities we discussed above (i.e. problem solving, communication, etc.). 

They tend to use the same traditional process of resume review and interviews which don’t do a good job of revealing which applicants actually possess these qualities. We’ve written at length about the ineffectiveness of this traditional hiring process—specifically as it relates to hiring for generalist roles like assistants. 

In short, relying solely on resumes and interviews is insufficient for understanding whether applicants will be good problem solvers or communicators on the job (or whether they’ll be trustworthy, reliable, organized, etc.). So VA companies that use this traditional hiring process end up providing inconsistent service. Sometimes their assistants work out and they’re good, but often their VAs are underwhelming and not worth the investment.

This problem of consistency—of being able to consistently find and hire the most capable assistants who have all of the right qualities—is the key problem we set out to solve when we started Persona.

The Hiring Methodology We Developed to Find World-Class Virtual Executive Assistants

We knew that in order to solve the consistency problem, we needed to leverage additional tools beyond just resumes and interviews when vetting applicants. So we applied our backgrounds in behavioral science and assessment design to create a more rigorous methodology for hiring assistants.

We use a range of quantitative and qualitative methods including (but not limited to):

  • Quantitative assessments: Tests that allow us to evaluate candidates accurately on key generalist abilities. 
  • Structured interviews: A strategic interview process to cross-compare candidates on the qualities and abilities that matter.
  • Work sample projects: Mock projects to see the quality of their work, based on the types of tasks they’re likely to do in a VA role.
  • Communication exercises: Exercises to evaluate candidates on key communication skills such as email etiquette. 
  • Reference and background checks: A structured approach to interviewing candidates’ references.

Our assessments, work sample projects, and exercises allow us to see how candidates behave and perform in the types of scenarios that they’re likely to encounter on the job. And every candidate that we evaluate is assessed in different ways based on how they perform at each step. 

For example, if a candidate has a critical reference who describes a weakness that the candidate has, we select a sample project for that candidate to perform in order to evaluate for ourselves the scope of that purported weakness.

Or, if we identify a bright candidate who expresses to us that they aren’t a fan of routine work, we move them to a more in depth survey stage to uncover what types of tasks do and don’t sustain their attention and what, for them, constitutes “routine” in their daily and weekly work schedule.

When we choose to hire someone, we’re not making assumptions about how we think they’ll perform—they’ve already proven they have the qualities and skills needed to have success in the role.

As a result, they’re able to go above and beyond our clients’ business needs and expectations. This includes competently managing common responsibilities of an executive assistant, such as:

  • Email management
  • Calendar management
  • Research and data entry
  • Bookkeeping
  • Personal assistant tasks like sending birthday cards, booking travel arrangements, and preparing itineraries

However, our clients also utilize our remote EAs for a wide range of other business functions as well. For example:

  • Project management: Manage the CEOs to-dos, ensure they stay up to date and on track with their key projects.
  • Business operations: Help to create, organize, and improve on internal business processes and standard operating procedures.
  • Marketing and social media management: Create and schedule social media posts, monitor engagement metrics, respond to comments, help grow overall online presence. 
  • People operations: Manage employee onboarding, assist in employee recruitment process (e.g. reviewing resumes and cover letters for certain criteria), manage payroll, etc.
  • Strategic planning: Work with the company leaders to define and come up with plans for new products, initiatives, and services. Project manage some or all of these new company programs. Considering the company’s goal and priorities, developing action plans to change processes or launch new projects that will be executed by other team members. Also, planning for various future business scenarios such as the launch of a new product or service.
  • Client services: Handle important interactions with clients or customers and provide ideas and feedback about how to improve systems and processes.
  • Special projects: Manage a wide variety of unique projects depending on what the executive needs. For example, our EAs have worked on things like graphic design in Canva, video editing, workflow design, building data sets, designing presentations, and more.

How Our Remote Executive Assistant Service Works

We provide world-class executive support for all types of industries, including tech startups, non-profits, real estate, professional services, and more. We serve C-level executives across the U.S.—in cities like Los Angeles, San Francisco, Boston, Austin, Miami, and New York—and internationally.

If you’re a founder, entrepreneur, small business owner, or senior executive of any kind, you can try one for a month or two and see how you like it. We require no long-term commitments. 

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 world-class assistant that equates to a full-time employee (40 hours of remote work per week, with no long-term commitment needed).

If you’re ready to try a remote executive assistant that can be truly transformative for your business, click here to get started. For testimonials from our clients, check out our homepage.

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