Business

The Process to Hire Executive Assistants is Broken. Here's Why We Started Persona to Fix It.

Jason Hreha
Nov 18, 2021
12
min read

We started Persona over 3 years ago with the mission of helping startup founders, executives, and business owners live better lives. Almost every business owner would benefit from a great assistant, but the process of finding and hiring a great assistant is much harder than it seems. There are dozens of mistakes one can make in hiring an assistant, and choosing the wrong assistant can be an absolute disaster — costing a surprising amount of time and money. In this article, we tell you how to avoid these costly errors.

The Process to Hire Executive Assistants is Broken. Here's Why We Started Persona to Fix It.

If you’re feeling overwhelmed, why don’t you just hire an assistant?

Executives and startup founders hear this from people in their network all the time. 

The idea sounds great in theory, but hiring a truly great assistant is much easier said than done

To understand why, let’s start with the variety of tasks a typical startup founder or executive is dealing with:

  • Scheduling meetings and non-stop calendar management
  • Managing a heavy influx of email
  • Doing research and data entry
  • Fundraising
  • Booking travel
  • Managing payroll
  • Sending thank you notes and birthday cards
  • Hiring
  • Ensuring new employees are onboarded
  • Creating presentations

These are just some of their work-related tasks. They also have long lists of personal tasks like ordering gifts for family members, making reservations for date night, and scheduling grocery deliveries.

These administrative and personal tasks eat up their time and keep them from focusing on the most important aspects of running their business.

It is true that finding an absolute rockstar assistant is transformative for founders and executives in the middle of this overwhelm. But finding amazing assistants is actually really difficult. 

It’s one thing to manage your own list of administrative and personal tasks. However, doing a really good job of managing these types of tasks (at this volume) on behalf of someone else requires a strong mix of savvy judgment, initiative, organization, and communication skills. 

The reason so many executives never find such an assistant is that traditional hiring practices don’t filter for the key traits an assistant needs.

In this article, I’m going to explain why finding a highly effective executive assistant is so hard. Then, I’ll explain how Persona has made it easier than ever to hire one that’s truly world class. 

Before I get to that, I’ll answer a common question lingering in the minds of founders: Is hiring an assistant really worth it?

The answer is... it depends. Let me explain.

Why Hiring an Average (Or Worse) Assistant Isn’t Worth It

Hiring an assistant won’t be worth it if you hire the wrong person. I know because of how many people tell me horror stories about their experiences. 

Often an assistant is good for the first week or month, and then things fall apart. They either stop showing up, they’re super disorganized, or they’re not very detail-oriented.

You ask them to have that presentation for you by Monday. Monday comes and goes—and there’s no presentation.

You ask them to book your flight for an upcoming trip. The week of the trip comes, and it turns out they purchased you a flight with a 6 hour layover.

The whole experience can become a nightmare, or, just as often, simply underwhelming and unhelpful. 

Other times assistants don’t work out because people don’t find them that useful. They’re only able to perform the most basic tasks. They can’t handle more complex and time consuming projects—or they need significant training to be useful (and that would require time you don’t have).

The core issue is that the hiring process didn’t properly filter candidates down to the best people for the job—the top 0.1% who possess the traits that highly effective assistants need.

That’s why people have these bad experiences so often. The traditional hiring process is flawed for finding a great executive assistant (more on this below).

If You Can Filter for the Right Traits and Find the Top 0.1% of Assistants, It Can Be Transformative for a Founder or Executive

You have to hire for quality if you want an executive assistant to be worth it. Once an assistant is good enough to take the tasks above completely off your plate, it's transformatively more useful than someone who can kinda sorta help with some of those tasks. 

Here are some examples of the differences between what the very best assistants can do—and what the vast majority of assistants can’t.

Example #1: Calendar Scheduling

An average administrative assistant can do basic scheduling, but their utility doesn’t go far beyond what Calendly provides. In contrast, a really good executive assistant can coordinate your schedule in a nuanced, sophisticated way. 

For example, they can look at your calendar, realize you have a scheduling conflict, understand which meeting is more important, and reach out to reschedule the less important meeting on your behalf. When they reschedule with someone, they can do so in a professional and personable way.

This means your assistant is able to:

  • Understand which people and meetings on your schedule need to take precedence.
  • Monitor and pick up on these conflicts in a timely fashion (and help you avoid last minute cancellations).
  • Maintain consistent and healthy communication with your team, investors, etc. 

These scheduling conflicts happen on a weekly (if not daily) basis. Compounded over time, this level of competency becomes exceedingly valuable. Your daily schedule can become a seamless, hassle-free experience.

This is the level of schedule management that the top 0.1% assistants we hire provide for our clients.

Example #2: Email Management

It’s not uncommon for founders and executives to receive hundreds of emails per day. Inevitably, important emails go unanswered, and too much time is spent processing irrelevant emails and notifications.

Many people would love for their assistant to manage their email for them, but assistants who can do this competently are rare.

An average administrative assistant can sometimes organize your incoming email into basic folders or send canned professional replies to people. But their overall utility for processing email is pretty low.

In contrast, a really good executive assistant can do more detailed coordination. For example, they can learn to understand and prioritize which emails need to be responded to by you, which ones can be ignored or set aside, and which ones they can respond to on your behalf. 

You can wake up in the morning with all of this done for you, only spend time on answering the emails that matter most, and save your cognitive capacity for the rest of your day.

These are just two examples of many kinds of tasks that Persona assistants manage for our clients. They can also help with tasks like:

  • Research
  • Data entry and analysis
  • Social media management
  • Travel planning
  • Personal tasks
  • Employee onboarding
  • Payroll
  • Presentations

For every one of these categories, there are equivalent examples that reinforce what we’ve found: top 0.1% assistants can handle these tasks with a level of sophistication that makes them vastly more useful than average assistants.

The Typical Approach to Hiring Executive Assistants

A lot of people don’t know where to begin when hiring an assistant. Often they’ll just tweet out, “Hey I need an executive assistant, can somebody help me?” Or they’ll post it on their careers page and then tweet about the open position. 

Others try freelancer sites and end up with an overwhelming number of applicants. Often founders and executives hiring for these roles are spread so thin and have so little time they’ll just give up. 

For those who are particularly determined, they’ll either click through resumes or hand them off to someone at their company to do this for them (often someone who's never hired before). 

They’ll look for superficial indicators that an applicant is qualified, like: 

  • How much experience they have.
  • Whether they worked for a blue chip company or brand name.
  • Whether they went to a good school.

Then, they’ll set up meetings to talk with a few candidates and choose the person they like the most. That’s the extent of their process.

Aside from being labor intensive, the overarching problem with this approach is that it's not rigorous enough, and it doesn’t measure the qualities that matter most in an executive assistant.

The Challenge of Hiring Executive Assistants with a Traditional Hiring Process

When you hire for a specialized role like Python Savant, you can assess candidates’ technical skills with a coding challenge or other skills-based tests. This provides you with an effective way to filter for the key abilities that will determine success in the role. 

For technical roles, there is less need to rigorously measure “generalist” traits to whittle down your candidate pool.

In contrast, when you’re hiring for a role like executive assistant, generalist traits like reliability, communication, and organization are the key traits that determine success or failure. 

That’s really hard to figure out using the traditional hiring process, which leads companies (and most recruiters) to make the following mistakes:

3 Mistakes People Make When Hiring Generalist Roles Like Executive Assistants

People who hire executive assistants make 3 core mistakes:

  1. They assess candidates on proxy variables that aren’t predictive of good on-the-job performance.
  2. They place too much emphasis on past work experience.
  3. They don’t measure the things that matter most when hiring a generalist.

1) Relying Too Heavily on Proxy Variables

Consider the criteria we normally use when hiring for generalist roles. We look at:

  • Which university the candidate graduated from.
  • Where they worked previously and for how long.
  • How well they respond and interact in the interview process.

There are a few other data points like references and a cover letter, but that’s really it. 

The process often goes something like this:

  • You look at what school they went to. You think, “They went to UC Berkeley, so they’re probably pretty sharp.” 
  • You look at their major and think, “They’re a mechanical engineer, that’s a hard major. They must be a quick learners.”
  • You have an interview with them and think, “We had a good conversation. They seem like an insightful person.”

Then you go with your gut. 

Notice how this entire process is based on assumptions and best guesses. We use these proxies to make assumptions about smarts, reliability, competence, and whichever traits or skills we might be looking for. But these assumptions can be wrong almost as often as they're right.


2) Too Much Emphasis on Past Work Experience

Most people place too much weight on past experience when they're hiring for an executive assistant role. If they get 100 applicants and only 10 of them have executive assistant experience, they inappropriately throw out all the other applicants and just look at the ones that have already been in the same role.

But an executive assistant is a generalist role. It doesn't require a lot of specialized knowledge or experience. Great employees in any role do many of the things that an executive assistant does for others on their own. 

They book their own flights, manage their own schedule, organize their own email, etc. 

What you’re looking for is someone who is smart, detail-oriented, and clear enough in their communication to do these tasks well, whether or not they’ve previously done it for others.

What’s worse, if you're hiring based on who has past experience on their resume, you're likely throwing out the best candidates. In a random sample of 1,000 smart and diligent college graduates, what percentage will already have held the title of "executive assistant"?

3) No Way to Measure the Things That Matter: Smarts, Character, and Communication

At the end of the day, there are 3 qualities that make a great assistant:

  • Problem Solving Ability: How smart are they? Can they figure things out in new and complex situations? 
  • Key Character and Behavioral Traits: Are they organized, reliable, detail-oriented, etc.?
  • Communication Ability: How well do they write and communicate? Can they communicate on your behalf or alongside you with key people (team, board members, investors, etc.)?

We intuitively know the importance of these qualities, but measuring them directly is not a standard part of the hiring process.

Very few companies have systems in place to test candidates for learning ability, so that quality is basically absent from the traditional hiring process.

The only way character traits and communication skills are measured are through assumptions made in the interview process. Companies hiring for in-person roles can bring someone into the office to get some sense of these, but it’s limited.

For example, it’s very difficult to figure out how detail-oriented or organized someone is during an interview—remotely or in person—and yet these are essential qualities in a good assistant. 

When hiring is being done remotely, the ability to measure these qualities is diminished even further.

Bottom line: Not only do most people not know what to look for when hiring generalist roles, they’re often actively focusing on the worst proxy variables to make their decisions. The process we’ve developed at Persona solves all of these problems.

We Experienced These Exact Hiring Issues and Founded Persona to Solve Them

We’ve discovered all of these issues with hiring assistants (and hiring in general) because we’ve lived through it. 

Specifically, before I founded Persona, I ran behavioral science globally for Walmart. I remember complaining to my cofounder Nathan about how hiring was always a 50/50 crapshoot. I felt like there had to be a better way.

Nathan and I have always been fascinated by psychology and human behavior, and we wanted to see if we could use our backgrounds to develop a more rigorous, data-driven approach to hiring.

We created a SaaS product that allowed us to measure candidates on key skills and character traits that we found through our research were predictive of on-the-job performance (i.e. the qualities I mentioned above that the traditional process doesn’t measure). 

It provided a detailed assessment of these key skills and traits and we were using it to find incredible people to come work for us as we built our own company. 

We knew we’d built something that would be an asset to companies looking to modernize and improve their hiring process. But we quickly noticed that at the end of the day, companies don’t care that much about how they get talent. They just want great talent. 

So we launched Persona.

The Difference Between Persona and Standard Recruiting Services

Most recruiting and placement companies use the same proxy variables I discussed above when vetting candidates for executive assistant roles. They don’t take a rigorous approach to measuring what really matters. 

In contrast, we’ve developed a unique and comprehensive process that allows us to make data driven decisions based on the things that matter most in generalist roles:

  • Problem Solving Ability: How smart are they? Can they figure things out in new and complex situations?
  • Key Personal Traits: Are they organized, reliable, detail-oriented, etc.?
  • Communication Ability: How well do they write and communicate? Can they communicate on your behalf or alongside you with key people (team, board members, investors, etc.)?

We use many different tools to assess these traits and abilities, including individually tailored combinations of:

  • Quantitative assessments
  • Pre-structured interviews
  • Work sample projects
  • Communications exercises
  • Reference and background checks

We customize our process on a case-by-case basis, evaluating different candidates in different ways based on their backgrounds and how they perform throughout each step. 

We’ve discovered that a mass and mechanical one-size-fits-all approach to hiring is simply unworkable if you want to find the absolute best candidates. By flexibly deploying a wide variety of vetting procedures, we’re able to understand our applicants on a deeper level, and figure out who will be the best performers for each of our clients. 

In the end, we hire roughly 1 assistant out of every 1,000 candidates. The result is that those who make the cut are able to perform at a much higher level than the assistants that founders and executives typically find.

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, fill out our form. You can try an assistant for a month or two and see how you like it. For testimonials from our clients, check out our home page.

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