How to Use an Executive Assistant: The #1 Thing to Focus On (Contrary to What Everyone Says)

Founders and business leaders who are working with an executive assistant for the first time often face a blank canvas problem. They know their assistant can help them manage email, schedule meetings, take phone calls, and handle other administrative tasks, but they often aren’t sure how to delegate these things—or sure of what else they should delegate.

To help executives in this situation, many thought leaders have popularized the approach of creating highly detailed, step-by-step systems for executive or administrative assistants to follow. And many executive assistant and virtual assistant services have begun doubling down on advertising their systems and “playbooks.”

They think a focus on developing the right systems is the key to effectively using an assistant, but we think the people and services touting this approach are missing something crucial.

The reason that executives and executive assistant services feel the need to develop really complex systems for their assistants is that they don’t focus on hiring really talented assistants in the first place. 

They hire average or low quality assistants, and then rely on creating step-by-step systems for them to follow.

Based on our experience providing executive assistant services over the last 3.5 years, we’ve found that if you focus on hiring great talent instead, creating these complex SOPs is unnecessary. You can share basic preferences and app logins with your assistant, and they can develop their own systems as they go. Among other benefits, which we’ll discuss below, this saves you the significant time and effort that it takes to create and customize these systems.

In this article, we describe how to effectively work with executive assistants, and provide the same recommendations we give to our clients at Persona.

Below, we’ll cover:

  • 3 problems with being overly reliant on standardized systems for your executive assistant
  • Useful advice for onboarding and getting started with your assistant (that strikes a balance between providing necessary details while not being overly prescriptive)
  • The process we’ve developed to hire world-class executive assistants that need much less prescriptive guidance

If you’ve been wanting an assistant but haven’t had the time to hire one, or have had bad experiences with your first executive 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.

3 Key Problems with Relying on Step-by-Step Systems for Your Assistant to Follow

We’ve talked with hundreds of founders and executives about their business needs when it comes to hiring an executive assistant. Through these conversations, it has become abundantly clear that no two entrepreneurs are the same. They each have different needs, preferences, and workflows for managing their business.

The first problem with relying on the step-by-step systems that different thought leaders and services prescribe is that they’re one size fits all. Most executives will need to spend significant time and effort customizing those systems to fit their own workflows, which in some cases is more work than starting from scratch to begin with.

The second problem is that step-by-step systems box in and limit what a great executive assistant can contribute. They don’t encourage growth, creativity, or autonomy—things that truly great talent desire in their working life. And they limit an assistant’s freedom to design even better systems that you yourself may not have thought of.

Lastly, the third problem is that you set a precedent in your working relationship that your assistant will always have step-by-step systems. When you want to expand their assistant duties to new things, the expectation is that you’ll create a specific set of instructions for them to follow. This works against you if what you ultimately want is a smart, autonomous assistant that can figure out how to do new things for you as you expand their responsibilities.

This is why we strongly encourage founders and executives to instead focus on hiring great talent first, because—if you know how to hire for the right qualities—they’ll require much less micromanaging and be more capable of taking on new things without much guidance.

Over the long-term, this significantly increases the value they deliver and can return far more than what you invest in them.

Below, we’ll discuss how we approach finding this level of talent, but first, let’s discuss the advice we think is useful when onboarding your executive assistant (assuming you’ve hired someone great).

How to Get Started Working with Your Executive Assistant (Without Developing Complex Systems or Being Overly Prescriptive)

When clients ask us about how they should get started with their assistant, we recommend a very simple approach.

First, choose the initial tasks you wish to delegate and go over them with your assistant.

For many executives, this includes email and calendar management, as well as other repetitive tasks on their to-do list such as filing expense reports, drafting memos, or updating QuickBooks. And in many cases, it also includes personal tasks such as making online purchases, meal planning, or booking travel.

Once you’ve discussed their initial set of tasks, provide them with your basic personal information and the preferences that are relevant for them to do what you want them to do.

For business-related tasks, this probably means granting them access to the various accounts and platforms you use on a regular basis to run your business (Slack, Trello, Google Workspace, Microsoft 365, QuickBooks, Webflow, Shopify, WordPress, etc.).

Our clients have found that using a password manager like LastPass or 1Password is useful for sharing credentials and adding an extra layer of security.

If you plan on having them do personal tasks for you in addition to business tasks, you can give them your key personal information as well. For example:

  • Address
  • DOB
  • License Number
  • Key Contacts
  • Login info
  • Doctor/Dental office information
  • Preferred pharmacy information

You also might provide them with your food preferences, your favorite places to eat for particular occasions (e.g. quick bite to eat alone, family, business, friends, etc.), as well as any food allergies or types of cuisines to avoid.

How to Delegate Email to Your EA

If you want to work toward delegating email management, first grant your assistant delegated email account access. This lets them access your email account without your password.

Once they’re inside, have them explore your last few weeks of emails to get a sense of the types of messages you get. In Gmail, this can be done by clicking on the “All Mail” tab. We’ve also found that it’s helpful to have your assistant spend some time going through your “Sent” box, so they can see how you respond to different types of messages with different people. This will start to give them an understanding of how you approach different issues and how you craft your messages.

Once they’ve familiarized themselves with your email, you and your assistant should have a conversation about what your perfect inbox looks like. For example:

  • What do you see each day when you open your inbox in the morning?
  • Which types of messages are most important?
  • Which ones do you want to get rid of?

The process of fully delegating your email takes time. It may start out as basic inbox organization (e.g. deleting promotional emails, tagging and categorizing, etc.), and then evolve into replying on your behalf over time as they learn your email style, who your important contacts are, etc.

There is no “right” system. The system you use should be tailored to your specific needs and preferences, and should evolve over time. And you shouldn’t have to prescribe it. Rather, you should be able to provide preferences and guidelines (e.g. keeping a close eye on investor emails during funding season), and let your assistant figure out how to develop and design systems that work for you.

How to Delegate Scheduling to Your EA

Similar to how you kick off your assistant with email, if you want to delegate scheduling to them, first give them calendar access. Have them look at your schedule over the last 2-3 months and get a sense of what your typical day looks like. Then, have a candid discussion about your goals and what your perfect day and week looks like. You can discuss things like:

  • Do you want more uninterrupted time to code or work on product?
  • Do you want to make sure that all of your meetings are crammed into one or two days each week?
  • Do you prefer to have no meetings before noon each day? Or no meetings on a certain day of the week?

Give your assistant a picture of your ideal schedule and let them take care of everything else. With a clear picture of what you want, a smart and reliable assistant can ensure that all the details and operations are taken care of.

For any other repeating tasks you want them to handle, just make sure they have the right access and information needed, send them a Slack request with what you want them to do, and ask them to do it.

In the first several months, while a focus on offloading repetitive tasks is useful, you don’t need to limit them to only administrative tasks. You can challenge them to take on more complex things, as well.

In fact, in our experience focusing on hiring high-quality talent, Persona assistants only spend about 30% of their time on basic administrative tasks. The rest of the time our clients use them in an extremely wide variety of ways to handle valuable and at times complex projects for the business.

The last time we checked in with our clients about the tasks our executive assistants manage for them, we were surprised by just how wide ranging they were. Here’s the list of all the unique tasks our assistants were executing:

  • Social media management on platforms like LinkedIn, Facebook, Twitter, etc.
  • Research
  • Email scraping
  • Building databases
  • Data entry, analysis, and management
  • Organizing files
  • Cold outreach
  • Inbox management
  • Calendar management
  • Business writing and drafting documents
  • Marketing support
  • Design
  • Content writing
  • Transcription
  • Online purchases
  • Video editing
  • Invoicing and billing
  • Human resource management
  • Employee onboarding
  • Workflow and project management
  • Travel arrangements
  • Excel spreadsheet management and data processing
  • Personal assistant tasks like sending birthday cards, booking flights and hotels, and preparing itineraries

Beyond these basic steps for getting started, our clients’ relationships and systems with their assistants tend to evolve naturally. We rarely hear from clients asking about how they can better utilize their assistants. They just identify and ask for the things they want help with, and their assistants get things done.

This is the type of relationship that we think most founders really want with their executive assistant. They don’t want to have to create a template for every task—they want to work with really smart people who can accomplish things with minimal guidance.

To have this type of relationship with your assistant, you need to have a hiring process that works for identifying top talent. Specifically, a process that vets candidates on the qualities that make great generalists—people who can competently handle a wide range of (mostly) non-technical tasks. That’s what we set out to create when we started Persona.

The Process We’ve Developed to Hire World-Class Executive Assistants (And How Our Service Works)

An effective hiring process for any type of role begins with understanding the qualities that applicants need to be successful. There are 3 key qualities that have been shown to predict success in an executive assistant role:

  • 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, business partners, etc.)?

The traditional hiring processes used by companies (and recruiters) don’t measure these qualities in concrete ways. They rely on superficial variables like where candidates went to school, where they worked previously and for how long, and how well they perform in their interviews.

But none of these variables provide concrete evidence of key things like problem solving ability, analytical skills, communication skills, or time management skills, for example. As a result, hiring for generalist roles like an executive assistant has traditionally been a 50/50 crapshoot.

This is the problem we set out to solve when we started Persona. We used our deep expertise in assessment design and cognitive science to build a hiring process that measures these key qualities.

We use individually tailored combinations of the following to vet our assistants:

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

Every step of our process is customized on a candidate by candidate basis, resulting in the ability to significantly increase our hit rate on finding and hiring world-class executive assistants.

At present, we hire roughly 1 assistant out of every 1,000 candidates. And it’s because of this tailored process that our assistants are able to effectively execute such a wide range of tasks with minimal guidance. 

How Our Executive Assistant Service Works

If you’re interested in working with one of our executive assistants, you can try it out for a month or 2 and see how you like it. We have 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 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.

We’ve helped hundreds of companies improve their executive office operations by pairing them with effective assistants who make enormous contributions to the c-suite’s productivity.

If you’re looking to find a great virtual assistant with stellar emotional intelligence, world-class problem solving ability, and excellent organizational skills, fill out our sign-up form and schedule a call with our team today. Join the many organizations and executives who love Persona, and who have used a Persona assistant to build a great business or climb the corporate ladder.

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