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

Executives and leaders like you got to where you are because you’re smart.

You have business intuition. You have skills. You’ve built up a reputation and a network. So you might look around and wonder, “Should I have an executive assistant?”

Many executives don’t realize what they’re missing out on. 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. EAs 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-level executive assistant does, you’ll see where we’re going with it.

Why Be An Executive Assistant?

Being an executive assistant can be a highly rewarding career for the right person. Working as an executive assistant provides a unique opportunity to work closely with high-level executives, gain valuable business experience, and make a real impact on an organization.

The best executive assistants find the role intellectually challenging as they navigate a leader’s day-to-day schedule and inbox while gaining exposure to strategic decision-making at the highest levels.

We asked our LinkedIn community of executive assistants what they wished others knew about the executive assistant role. With more than 300 votes, there was an overwhelmingly clear winner: demanding.

LinkedIn poll by Boldly Premium Executive Assistants. The poll asks 'One thing most people don't realize about the executive assistant role is how _______ it can be.' Results: Demanding 50%, Rewarding 25%, Strategic 18%, Lonely 7%

Working as an executive assistant isn’t for the faint of heart. It takes a very specific mindset, skillset, and years of experience.

For those with strong organizational, communication, and problem-solving skills who thrive in a fast-paced environment, having executive assistant experience can open doors to exciting career advancement opportunities.

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 no longer relevant in today’s business world.

Although a new generation of leaders might say they’re happy scheduling their own meetings and travel plans (or using AI tools to do it), the point is that they shouldn’t be. It’s a costly mistake.

Their focus should be on high-leverage decisions and strategy. Leaders who don’t understand the value of an EA are losing precious time and energy on tasks that are better suited to a great executive assistant who can do it more effectively and faster than they can.

While the technology and expectations 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. 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. Could AI replace a high-level executive assistant?

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 remote 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.

Not all executive assistants are as equally capable, and that’s why some might think an EA is replaceable.

Signs Of A Bad Executive Assistant

While a great executive assistant can be a huge asset, there are some red flags to watch out for that may indicate an executive assistant is not up to par:

  • Frequently missing deadlines or letting important details slip through the cracks
  • Poor communication and interpersonal skills that damage relationships
  • Lack of proactivity and always waiting to be told what to do
  • Inability to learn and adapt to the preferences and working style of their executive
  • Indiscretion with confidential information Executives should be aware of these ((signs of a bad executive assistant)) and address issues promptly before they escalate.

If an executive assistant is performing poorly, it’s easy to understand why some might question the need for one at all.

How To Be The Best Executive Assistant

Reaching the top tier of executive assistant roles requires a combination of hard and soft skills. The best executive assistants are:

  • Highly organized and detail-oriented with strong project management abilities
  • Emotionally intelligent and able to communicate effectively with people at all levels
  • Proactive problem-solvers who anticipate needs and take initiative
  • Adaptable and able to shift gears quickly in a fast-paced environment
  • Committed to always expanding their business knowledge and skills By continually honing these key traits, assistants can set themselves apart and deliver exceptional value to the executives they support.

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.

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 for us, 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 means you only pay for what you need and can adjust hours as required.

You get:

  • 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
  • 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

About the author Katie Hill is a Content Writer at Boldly, which offers Premium Subscription Staffing for demanding executives and founders. When she isn't writing about remote work or productivity, she can be found adventuring in Colorado's backcountry.

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