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Working As A High-End Executive Assistant Isn’t Rocket Science (But It’s Close)

Written by: Sandra Lewis

Executives got to where they are because they’re smart. 

They have business intuition. They have skills. They’ve built up a reputation and a network. It’s strange, then, that when it comes to executive assistants, there are two mistakes executives make:

  1. They think they don’t need one.
  2. They think all executive assistants are the same.

Being a high-end executive assistant isn’t rocket science, but in the business realm, it’s a close comparison. They are mission control. There’s a lot on their radar, and some of those trajectories will collide without their input.

Maybe that’s wearing the comparison a little thin, but once you understand what a high-end executive assistant does, you’ll see where we’re going with it. We’ll paint that picture by answering two questions, and then giving you a reality check on what those top-shelf executive assistants really do.

Are Executive Assistants Vanishing?

Despite what you’ve heard about the vanishing executive assistant, no. High-end executive assistants aren’t going anywhere.

Don’t confuse changes in technology and job description of what an executive assistant does as proof that they’re a dying breed. And while new generations of leaders might be happy scheduling their own meetings and travel plans, the point is that they shouldn’t be, because it’s a costly mistake.

They have better things to do with their time, and they’re making a bad decision because they don’t know what a great executive assistant really does.

While the technology and expectation may shift and change, the need for an executive assistant is always steady. Busy high-level executives still have the same needs, no matter when or where they are.

Are Executive Assistants Replaceable?

If you think you could skirt around getting an executive assistant, it’s worth asking what they do. We could give you a list of skill sets and preferred experiences, but instead, let’s take a look at what an executive assistant does from a different angle.

  • They have to sift through a barrage of communication. No algorithm can replace a human being with intuition and knowledge honed by years of general experience and a relationship with the executive. The same kind of communication, from different people, may have different values. Executive assistants have to understand context, habit, and preference.
  • They have to be archivists. At any moment, they may need to remember or locate information from clients, data, or past communications as needed.
  • They have to be mind readers. Obviously, no one can read minds, but a great executive assistant works so well, and is so observant and quick to learn from those observations, that he or she will know what their executive will want or need before they do. Executive assistants are beyond being micromanaged. They are prepared before they need to be, whether that’s in being ready to offer input, having information ready, or planning a schedule based on likely contingencies.
  • They instigate a shift for their executive. When a high-level executive doesn’t have an executive assistant, they are the executive assistant. That should tell you the high-value nature of the work an executive assistant does. But it also shows the incredible shift that should happen for the executive once all of the tasks and duties are removed from their plate and onto the assistant. It should be noticeable.
  • They have to be able to juggle. No, not like a circus clown. But an executive assistant is going to have lots of moving parts up in the air at the same time, juggling meetings, communication, and much more, all at once. It’s like a puzzle where the pieces are constantly moving, and you can’t panic about it.

That list is so multifaceted that it doesn’t seem like artificial intelligence could legitimately enter the equation, yet AI is under consideration as a solution for replacing people across lots of industries.

I recently gathered some of Boldly’s most experienced executive assistants together to talk about how artificial intelligence could play a role in the future as far as supporting some of the most complex tasks that executive assistants manage, possibly making scheduling meetings for c-suite level executives much easier. I wanted to know if executive assistants could be replaced entirely, or just in part.

That discussion was an eye opener.

Let’s say you were asked to schedule a meeting for five very senior executives, all who have extremely busy schedules. What needs to be considered? How do you go about finding a time that works?

Using Calendly or Doodle, or a similar automated calendar scheduling app, isn’t going to cut it at this level.

And more to the point, how do you interpret the instructions given to you by your executive about the meeting? Not all meetings are created equal, and it’s rarely possible for you to ask lots of questions. These are busy executives; you have to figure it out and infer (i.e. be a “mind reader”) based on what you’re given.

You have to find clues, and recognize them as such.

One of our executive assistants explained that if her executive calls her Cat instead of Catherine when she is cc’d on an email to a fellow executive, suggesting they set up a meeting, she knows the level of formality she needs to follow.

There are other cues to look for. 

How urgently does the meeting need to be scheduled? Who is to be invited? Who are the power players that get first dibs at suggesting a time? Who calls the shots, and who defers to the needs of others? How do you schedule a meeting in relation to what’s already on the executives’ calendars? What’s the relationship between the invitees that might determine the tone with which the meeting invite should be written?

Then it gets more practical. You have to determine a location and factor in travel time, and you have to have a plan for if/when the meeting needs to be rescheduled–which happens frequently!

This level of ability to communicate not only by what’s said, but infer based on known preferences and past experience will require very sophisticated AI to replicate. What will AI do with these kinds of clues? At what point will it be able to recognize them as such?

High-end executive assistants are currently irreplaceable because they have the ability to discern what’s required and implement it at a standard that is currently beyond even the most advanced AI scheduling functionality.

A High-End Executive Assistant Is A Partner

When the work style, trust, and relationship are solid, a high-end executive assistant is a partner to the executive.

They understand that how they work, including the way they schedule a meeting, reflects on their executive; it’s something that can make a huge difference in delicate situations where business is at stake.

That’s why there’s a difference between an average executive assistant and a high-end executive assistant. The complexity of tasks, the level of responsibility, and the ability to discern what needs to happen is why senior executive assistants are worth their weight in gold.

This is what we specialize in, at Boldly.

You can find an executive assistant in many places. There are lots of solutions out there.

But in our book, unless it’s high-end and top-quality, it’s not really a solution.

So, when we get tens of thousands of job applications, we only pick the best; only the most experienced, with Fortune 500 or c-suite experience, are hired onto our team. We are serious about our vetting, and to the same degree, we’re serious about making sure we match our clients with the right person

The best part is we make all of this available to anyone, easily.

Subscription staffing, meaning you only pay for what you need and can adjust hours as required. Support from us, to let us know how things are going. Quick startup time, since you don’t have to go through a hiring process. And no concerns over compliance, since our executive assistants are our employees and we handle payroll and other legal issues.

Are you tired of being your own executive assistant? All you need to do is contact us; we’d love to talk to you!

Topic: Remote Executive Assistant

Updated on December 19th, 2022

About the author: Sandra Lewis is the Founder and CEO of Boldly. She's passionate about helping Businesses, Organizations and Executives increase productivity and move their work forward with the right skills and resources. Setting an example of the efficiencies gained working remotely, she’s been leading her entire team on a virtual basis for the past decade.