Remote Executive Assistant: What to Know Before You Hire

How do you hire a Remote Executive Assistant?

Over the last 4 years running our executive assistant service, we’ve spoken with hundreds of founders and entrepreneurs about their needs for an executive assistant (EA). And through those conversations, we’ve learned that many execs who’ve worked with EAs in the past have had lackluster experiences.

The reasons why vary, but often they tell us things like: 

  • Their assistants weren’t that organized.
  • They didn’t have adequate communication skills.
  • They required a lot of micromanaging.
  • They couldn’t rely on them to get things done on time.
  • They seemed great on paper or in their interview, but didn’t meet expectations once they were on the job.

At some point, each of these execs either a) gave up on hiring an EA or b) fired their assistant and went back to the hiring process. 

This can be an incredibly frustrating experience, and it’s common both for executives who hire EAs in-house, as well as those who use outside services like recruiters and staffing agencies (more on this below).

Based on our experience vetting thousands of executive assistant applicants each month, we’ve learned that the #1 problem leading executives to have this experience is that most people who hire EAs lack effective ways to evaluate candidates on the qualities that make great executive assistants.

In this article, we’re going to explain:

If you’ve been wanting an assistant but haven’t had the time to hire one, or have had bad experiences with them in the past, 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 Great Executive Assistants (and Why They’re Hard to Evaluate)

Founders and executives have an intuitive sense that they want their assistants to have excellent communication skills, be great problem solvers, and possess key character traits like reliability and detail-orientedness. And in fact, these are the qualities—what we call “generalist aptitudes”—that the best EAs have. 

When EAs possess these qualities and traits, they’re well suited to reliably and competently execute the types of administrative tasks c-level executives need. For example:

  • Calendar management
  • Scheduling meetings
  • Making travel arrangements
  • Doing research and data entry
  • Safely handling confidential information

When EAs are great problem solvers (i.e. they can think quickly on their feet, and figure things out in new and complex situations), there are two additional key advantages: 

  1. The range of what they can do extends beyond these core responsibilities to encompass a diverse array of other complex tasks (Think: redesigning company workflows or managing special projects).
  2. They require far less micromanagement or guidance on your part. You can simply ask them to get things done, and they can figure out how to do it.

This is incredibly valuable for senior level executives who lack the time or patience to spell out how to do different tasks, and would love the ability to ask their assistant to handle tasks outside of the standard set of EA responsibilities.

However, in practice it turns out that evaluating generalist qualities like problem solving ability, communication ability, and particular character traits is difficult—so most people don’t really measure them.

There Isn’t the Equivalent of a “Coding Challenge” for Evaluating EA Candidates

When hiring for technical roles, there are often concrete ways of measuring the abilities of job applicants. Giving engineering candidates a coding challenge is a quintessential example of this.

These types of skills tests make it possible to see the abilities of job candidates before they’re on the job, which leads to much more consistent outcomes when hiring.

In contrast, most companies do not have an equivalent test or way to measure the generalist abilities of executive assistant job candidates. Instead, they rely on proxy variables (e.g. where they received their bachelor’s degree, years of experience, etc.) to judge the quality of applicants, and make assumptions about how applicants will perform in the role based on those variables.

For example:

  • “They went to Berkeley. They’re probably a pretty good problem solver.”
  • “Their resume looks tight. They’re probably pretty detail-oriented.”
  • “They were at their last job for 3 years. They’re probably pretty reliable.” 

Assumptions like these are incorrect as often as they’re correct, so they don’t tend to be accurate predictors of how a candidate will perform on the job. And interviews—while they’re certainly still an integral part of a good hiring process—also don’t concretely measure any of these key qualities.

For example, how well a candidate answers questions about their character or problem solving ability doesn’t necessarily translate into on the job performance either.

As a result of these hiring practices, the outcomes of hiring are inconsistent, and employers only find out the true capabilities of their EAs once they’ve already been hired. If the EA doesn’t perform how they’d expect, they have to go back to the drawing board, expending more time and effort on the hiring process (with an equal chance of making another hire that doesn’t work out)

This is the problem we set out to solve when we started Persona. We asked: How can we develop a system that concretely measures EA applicants based on the qualities that really matter (before we hire them)?

Below we’re going to explain the methodology we designed to do this. But before we get to that, we mentioned above that these same hiring outcomes often happen when companies use recruiters and staffing agencies, so we’re going to briefly cover why that is first.

Note: If you aren’t an executive, but rather someone who’s looking for job postings for a full-time remote executive assistant job, or want to learn more about becoming an executive administrative assistant, click here to explore working with us. (We do not offer part-time roles.)

Outside Services Like Recruiters & Staffing Agencies Also Lack Effective EA Hiring Processes

Many companies (especially startups) choose to outsource the hiring of administrative support roles like executive assistants. This saves them the time and effort of doing the hiring themselves, and allows them to prioritize other essential things in their business.

However, in our experience, most recruiters and staffing agencies use the same ineffective hiring practices we described above. They don’t have sophisticated ways of evaluating candidates on the 3 key qualities we covered earlier (problem solving, communication, and key character traits), so companies that use these services often experience equally inconsistent hiring outcomes.

And particularly when working with recruiters, they also face misaligned incentives from the way that recruiters are paid. 

We’ve written at length about these issues in a past article, so we won’t go deeply into them here. To learn more, read this post on why you shouldn’t work with a recruiter to hire your executive assistant.

Now, let’s look at the solution we’ve developed to more rigorously evaluate EA candidates and find top talent for our clients. 

Our In-Depth Hiring Methodology for Finding World-Class EAs

We leveraged our backgrounds in assessment design and cognitive science to develop a hiring methodology focused on evaluating the 3 key qualities in EAs: 

  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, 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.)? 

Our methodology involves an in-depth vetting process that quantitatively and qualitatively measures candidates on these abilities. It includes a mix of 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.

Every step of our process is customized on a candidate by candidate basis, based on how each applicant performs as they progress through each step. 

For example, if we like the quality and sophistication of a candidate’s writing samples, we may employ additional steps to figure out, “How quickly and consistently can this candidate produce this level of writing?”. 

Or, if we determine that a candidate has good problem solving ability but may not have the necessary tech-savviness to work with our c-suite clientele, we take additional steps to measure the candidate’s abilities in navigating modern software tools and interfaces. 

Due to the rigor of our methodology, we’re able to consistently find top talent that’s capable of thriving in a dynamic work environment. This includes competently executing all of the EA basics, for example:

  • Becoming an executive’s main point of contact
  • Executive calendar management
  • Email management
  • Transcription of Zoom meetings, phone calls, etc.
  • Acting as a stand-in for meetings requiring executive commitment and presence
  • Research and data entry
  • Making travel arrangements
  • Creating filing systems (e.g. for organizing expense reports or other recurring documents that need tracking)
  • Invoicing and billing
  • Bookkeeping
  • Human resource management
  • Personal assistant tasks like sending birthday cards, booking flights and hotels, and preparing itineraries

However, because we hire for generalist problem-solving ability, our EAs are often quick to pick up a wide range of tasks outside of traditional EA responsibilities. For example, here are some of the other activities our clients have told us our EAs help them with:

  • 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 web design, video editing, workflow design, building data sets, designing Microsoft Powerpoint presentations, and more.

This range of tasks and breadth of capabilities demonstrates that when you hire people who are really smart, and have the right character traits and communication skills, the value they deliver can extend far beyond what you put in your job description.

How Our Virtual 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, senior executive, or executive director interested in trying out one of our EAs, 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).

Whether you’re looking for an assistant to coordinate meetings between internal and external executives, manage multiple executive schedules, oversee internal and external meetings, perform administrative tasks, perform remote general office duties, or handle recurring executive requests, Persona can help. We support startup founders, corporate executives, executive business units, hedge funds, venture capital firms, and more.

It doesn’t matter if you’re looking for an assistant for yourself, your Head of Product, or your Chief Financial Officer, we’re ready to support you and your team. A Persona executive assistant handles all the tasks a traditional executive assistant or administrative assistant performs, and much much more. You can think of Persona EAs as senior executive assistant level talent, but capable of project management and other complex responsibilities.

Stop posting remote executive assistant jobs. Let us match you with someone great today.

If you’re ready to try an 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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