Startup Executive Assistants: Why Who You Hire Is Everything

When hiring an executive assistant (EA), startups have unique needs compared to a small business or large Fortune 500 company. 

In addition to traditional forms of administrative support like email and calendar management, startups need assistants who can:

  • Wear many different hats. It’s essential for team members—especially executive assistants—to be capable of contributing to tasks and responsibilities outside of their job description.
  • Perform under pressure in a fast-paced environment. Time frames in which goals and milestones must be achieved are shorter in startups. This means there’s added pressure to perform at a high-level with constrained resources and time.
  • Adapt to constant change. Startups undergo more change than most businesses, so startup employees need a greater ability to adapt to constant change.
  • Learn new technologies quickly. Startups tend to be more tech-enabled than other businesses, so startup employees need greater tech-savviness than most businesses require.

As a result of these unique needs, finding an executive assistant who will thrive in a startup environment is more challenging than finding one who might be sufficient in other types of businesses. 

Simultaneously, the stakes are much higher for startups because a) high-growth startups often have an urgent need for help and b) they don’t have the time, human resources, or expertise for recruiting niche or one-off roles like an executive assistant. 

Startups in this position often look to outside services like recruitment or staffing agencies to help them find the right person for the role. However, most third party recruiters and staffing services lack sophisticated methods for evaluating applicants on the qualities that make effective startup EAs—so often this strategy leads to poor hiring outcomes.

In this article, we’ll discuss why this is and share the alternative solution we’ve developed at Persona. Specifically, we’ll cover:

  • The qualities that make top startup executive assistants (i.e. the key criteria candidates should be evaluated on)
  • 2 problems with the way most companies, recruiters, and staffing agencies evaluate EA candidates
  • The hiring methodology we’ve built that enables us to find top EA talent for startups

Note: Our unique hiring methodology enables us to find world-class executive assistants for our startup clients. We hire roughly 1 out of every 1,000 candidates. 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. For testimonials from our clients, check out our homepage.

The Qualities That Make Top Startup Executive Assistants

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 effective in a startup EA 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 highly motivated, resilient, organized, 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-Savviness: 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?

On some level, these qualities are important for an EA to have in any type of business. For example, having strong communication skills is something that EAs need to be effective at any company.

However, qualities like problem-solving ability and tech-savviness—as well as certain character traits like resiliency and motivation to work hard—become even more important in the dynamic work environment of a fast-paced startup. 

For example, greater problem-solving ability corresponds to an assistant’s ability to wear different hats (i.e. take on tasks and responsibilities outside of their job description) and adapt to rapid change (i.e. figure things out in new and complex situations). 

Greater tech-savviness corresponds to an ability to quickly learn new software programs that startups use to run their businesses. Where basic email, calendar, and Excel familiarity may be sufficient in many companies, effective startup EAs should be able to master whichever technology platforms companies are using to run their operations (e.g. Notion, Trello, Airtable, HubSpot, Superhuman, etc.). 

The challenge is that most startups—as well as third party recruiters and staffing agencies—don’t have the know-how or resources to thoroughly vet applicants based on these qualities. In the next section we’ll look at why.

Two Problems with the Way Most Companies and Recruiting Services Evaluate Executive Assistant Candidates

There are two key problems with the way executive assistant candidates are traditionally evaluated. Specifically, companies and recruiters tend to: 

  1. Look for the wrong things in candidates
  2. Rely too much on resumes and interviews in their evaluation process

Let’s look at each.

1. They Look for the Wrong Things When Evaluating Candidates

The variables that companies and recruiters tend to look at when evaluating EA candidates are things like: 

  • Past experience in an assistant role
  • How long they were at their last job
  • Where they went to school

But these variables don’t concretely measure any of the key qualities we discussed above (i.e. problem-solving ability, communication ability, etc.), and they’re not predictive of how well someone will perform in an EA role.

For example, take the common practice of filtering and sorting applicants based on years of experience in the role. The fact that someone has past experience as an assistant doesn’t tell you anything concrete about that person’s performance. Just because someone was an assistant for many years doesn’t necessarily mean they were a good assistant. And years of experience tells you nothing about their problem-solving ability, tech-savviness, or communication ability. 

Furthermore, if someone is smart, tech-savvy, and a great communicator—do they really need to have past experience as an assistant to be capable of performing well in that role?

In our experience, the answer is no. In fact, often the best candidates do not have past experience as an executive assistant. Judging candidates on these types of common criteria is flawed and doesn’t actually yield the best hiring outcomes. 

2. They’re Overly Reliant on Resumes and Interviews

In addition to focusing on the wrong variables, most companies and recruiters also rely almost exclusively on resume review and interviews when evaluating candidates. The implications of this are two-fold. 

First, companies tend to make assumptions about candidates based on superficial variables. For example, they might assume a candidate is reliable if they were at their previous company for several years. Or, they might assume a candidate is a good problem-solver because they went to a particular school like Cornell or UC Berkeley. 

Clearly these assumptions do not always turn out to be true.

And second, when interviews are the primary method for evaluating talent, companies are limited when it comes to measuring candidates thoroughly on their abilities (even if they try to vet candidates on the right qualities). 

For example, they can ask candidates problem-solving questions about how they’d approach certain scenarios. But it’s still theoretical. It’s not concrete evidence of their ability to solve problems in practice on the job.

This over-reliance on resumes and interviews—and the subsequent assumptions that get made about candidates—are at the heart of why hiring outcomes for assistants are so inconsistent. This approach leads businesses to only see how assistants perform once they’re on the job. At that point, if they aren’t as talented as they appeared or assumptions turn out to be wrong (and they often do), companies are back to square one.

Now let’s look at the hiring methodology we’ve developed at Persona to solve these problems. 

Our Methodology for Hiring World-Class Executive Assistants

When we started Persona, we wanted to design a hiring process that would a) focus entirely on assessing qualities that predict success in an executive assistant role and b) thoroughly evaluate those qualities in concrete ways.

We did not want to be subject to relying on assumptions or ambiguous evidence that candidates would make great EAs on the job. We wanted to know for sure that they would be able to perform at a high level—by way of having them prove it to us—before actually hiring them.

To accomplish this, we used our backgrounds in behavioral science and assessment design to develop a hiring methodology that leverages the following:

  • 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.

By coupling assessments, exercises, and projects with traditional forms of candidate review (i.e. resumes, interviews, reference checks), we have a far greater ability to ensure we only hire EAs that have proven they can perform well as the right-hand to a founder (or co-founder).

And in addition to using a wider range of tools when assessing candidates, we also customize our process on a candidate-by-candidate basis.

For example, if a candidate has a critical reference who describes a weakness that the candidate has, we select a sample project to zoom in and further evaluate them on that purported weakness.

Or, if we determine that a candidate is intelligent but may not have the requisite tech-savviness to work with our startup founder clientele, we take additional steps to measure the candidate’s ability and fluency in navigating and reasoning about modern software apps and interfaces.

As a result of our more advanced and thorough hiring methodology, we’re able to provide assistants whose capabilities range widely and beyond standard administrative tasks.

Generally, our EAs manage some combination of the following for our startup clients:

  • Communications: Manage email, communicate on an executive’s behalf and alongside them with company staff members and key stakeholders, draft company memos, etc.
  • Scheduling and time management: Manage an executive’s calendar, schedule internal and external meetings and appointments, resolve scheduling issues, balance personal appointments with work meetings.
  • Project management: Manage the CEO’s to-dos, ensure they stay up to date and on track with their key projects.
  • Business operations: Help create, organize, and improve on internal business processes and standard operating procedures. Manage administrative assistant tasks such as filing expense reports.
  • Marketing and social media management: Create and schedule social media posts on top platforms like LinkedIn and Facebook, monitor engagement metrics, respond to comments, help grow an overall online presence. 
  • People operations: Manage employee onboarding, assist in the 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. 
  • Client services: Handle important interactions with clients. Provide ideas and feedback about how to improve systems and processes.
  • Special projects: Manage a wide variety of unique projects depending on what your executive needs. For example, our EAs have worked on things like web design, video editing, designing Microsoft Office PowerPoint presentations, event planning, workflow design, building data sets, and more.
  • Personal assistant tasks: Help make online orders, reservations, travel arrangements, and other accommodations for executives’ personal lives.

How Our Remote Executive Assistant Service Works

We serve C-level executives and entrepreneurs at fast-growing startups across the U.S.—in cities like Los Angeles, San Francisco, Boston, Austin, Miami, and New York—and internationally.

We require no long-term commitments and can work with executives in any timezone.

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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