Flexibility Equation: Why EAs Need Flexibility

The Flexibility Equation: Why Senior Executive Assistants Shouldn't Always Follow the Standard Office Schedule

We spend a lot of time talking with companies about hybrid work and one of the conversations we find ourselves having repeatedly is this:

“Our company policy is in-office five days a week.”

Fair enough.

But when the position we're discussing is a Senior Executive Assistant supporting a CEO, founder, C-suite executive, or leadership team, our next question is usually:

Does this particular job actually operate like everyone else's job?

Very often, it doesn't.

At the highest levels of executive support, an EA's working life is built around the working life of the executive they support and the working life of a CEO rarely fits neatly between 9:00 AM and 5:00 PM, Monday through Friday. The EA may be answering a text at 9:30 PM because a flight changed. They may scan their email before they have even left home in the morning because their executive is already awake in London. They may respond to a board member after dinner, move tomorrow morning's meetings because something happened overnight, notice a travel issue on a Sunday afternoon, or keep one eye on their phone while their executive is navigating a particularly complicated week.

That doesn't mean they're sitting at a desk working 24 hours a day but they are often carrying a level of professional responsiveness that extends far beyond the hours they physically spend in an office. We believe that matters.

Senior Executive Support Is Different

This isn't about suggesting that an Executive Assistant's job is more important than everyone else's. It is about recognizing that it is structurally different. Many roles within a company have relatively defined working hours. When the workday ends, there is a reasonable expectation that the employee can disengage until the next morning.

Senior executive support frequently doesn't work that way. The best EAs become deeply integrated into the operating rhythm of the executives they support. They know what is happening tomorrow, next week, and next quarter. They anticipate problems. They monitor shifting priorities. They know when something genuinely requires immediate attention and when it can wait. Most importantly, they make themselves flexible when their executive's life requires flexibility. That is part of what separates an excellent senior EA from more traditional company roles.

So when companies tell us they want someone who is extraordinarily responsive, anticipatory, adaptable, discreet, available across changing circumstances, and willing to occasionally accommodate early mornings, evenings, travel, or different time zones - but that person must also sit at the same desk from the same hour to the same hour every day because that's the company (blanket) policy - we think it's worth examining whether those two expectations actually fit together.

Flexibility Should Work Both Ways

Think of flexibility almost as an exchange. If you want an EA who will say:

"Absolutely, I'll handle it!" when your 7:00 PM flight is canceled, there should probably also be days when that EA can say:

"You're traveling this week, everything is covered, and I'm going to work from home tomorrow."

If your EA is monitoring your inbox before normal business hours because you're overseas, perhaps they don't need to be sitting conspicuously at their desk until 5:30 PM simply because everyone else is. If December 23rd is technically an office day but the executive is already on vacation and there is little reason for the EA to physically be there, perhaps working remotely is (likely) entirely reasonable.

If the executive has spent three weeks traveling and the EA has been managing changing itineraries, late-night texts, early-morning logistics, and everything happening back at headquarters, perhaps there should be some natural give-and-take when there is room for it. Not necessarily through an elaborate written formula - sometimes it's simply the culture of the relationship. “You are flexible for me, and I am flexible for you.”

This Isn't About Working Less

This distinction is important. We aren't advocating for senior EAs to work fewer hours than the job requires, disappear during the day, or receive blanket exemptions from accountability. Quite the opposite. High-performing Executive Assistants are often extraordinarily accountable'; the question is whether we should measure that accountability by presence or by performance.

Did the executive get where they needed to go? Was the calendar managed? Were priorities anticipated? Did the board materials go out? Did the EA catch the conflict nobody else noticed? Was the executive prepared? Were the right people followed up with? Did something fall through the cracks? Was the EA accessible when it actually mattered? For a truly senior EA, those questions tell us much more about performance than whether someone was physically sitting at a desk at 4:47 PM on a quiet Friday when no one is even in the office that they support or work closely with.

The Career Equation Is Different, Too

There is another piece of this conversation that companies sometimes overlook. A talented employee who joins a company as a junior software engineer, marketing associate, or financial analyst may reasonably expect their career to evolve through a series of promotions, titles, compensation increases, equity opportunities, management responsibilities, and increasingly senior positions.

Executive support careers can absolutely grow, too! Great EAs can become Senior EAs, Executive Business Partners, Chiefs of Staff, Directors of Executive Operations, or leaders of administrative teams.

But sometimes the goal is different. Sometimes a exceptional EA finds the executive they want to support for the next ten years - and frankly, that's exactly what many executives tell us they want! They don't want their EA thinking about their next promotion every eighteen months. They want someone exceptional to learn them, understand their business, know their family, remember the board dynamics, understand how they travel, know who gets through immediately and who doesn't, and build years of institutional knowledge.

They want that person to stay and that creates a responsibility on the employer's side of the equation, too.

If traditional upward mobility is more limited because the ideal outcome is longevity in the role, then the role itself needs to become increasingly attractive over time.

Compensation matters. Bonuses matter. Benefits matter. Respect matters. Autonomy matters. And flexibility can become an incredibly valuable form of career currency.

The Irony of Requiring an EA to Be in the Office When Their Executive Isn't

There is also a practical question we encourage companies to ask: Where is the executive? If a CEO travels 40% of the year, does their EA genuinely need to be sitting outside an empty office five days a week?

Sometimes, the answer is yes - mostly. An EA may need to be physically present to build relationships, keep their ear to the ground, participate in key meetings, and attend company-wide All Hands or leadership standups. In these environments, the EA can be an important in-person presence for the broader leadership team. They may also own meaningful responsibilities that simply need to happen on-site, or the nature of the company’s operations may genuinely require their physical presence. But sometimes the answer is simply: “Because that’s our policy.” “We need to be consistent.” “We don’t want to set a precedent.” “If we allow flexibility for one person, we have to allow it for everyone.” Or some variation of the same reasoning.

That's where we think companies should dig a little deeper.

The purpose of an Executive Assistant isn't to demonstrate compliance with an attendance policy. The purpose and responsibility is to make the executive more effective. If that can occasionally be accomplished just as effectively - or sometimes more effectively - from somewhere else, rigid adherence to an unrelated company-wide policy can become counterproductive. This is a position unlike the others around them.

Flexibility Is Also a Retention Tool

The very best Executive Assistants have options. They are sophisticated professionals managing extraordinarily complex working relationships, and companies compete for them. In our experience recruiting senior executive support talent, candidates increasingly evaluate flexibility as part of the entire compensation package - not necessarily because they want to work from home five days a week.

Many senior EAs actually enjoy being in the office. They understand the value of proximity to their executive and leadership team. They know how much information is absorbed simply by being present. What they often want is trust and reasonableness. They want to know that after demonstrating extraordinary commitment to an executive, that commitment will be reciprocated. They want an executive who understands that flexibility isn't a loophole - it's part of a mature professional relationship.

Hybrid Doesn't Have to Mean Tuesday and Thursday

Perhaps this is where companies get stuck. When they hear "hybrid," they picture a formal policy:

Monday, Wednesday, Friday in office. Tuesday and Thursday remote.

But senior executive support often requires something much more nuanced - maybe there isn't a fixed remote day at all. Maybe flexibility follows the executive's calendar, perhaps the EA is in whenever the executive is in. Maybe they're remote occasionally when the executive travels. Maybe they leave earlier after an unusually early start to the day, when they had to be in to prep with the CEO for an important meeting. Maybe there is more flexibility during quiet periods and less during board weeks. Maybe they work remotely around the holidays when the office and executive are both quiet. Maybe everyone simply uses good judgment.

For senior professionals, discretionary flexibility can sometimes work better than scheduled flexibility. It allows the role to flex with the executive rather than forcing both people into another rigid structure.

Trust Is Part of the Job Description

There is something else worth considering. We trust senior Executive Assistants with extraordinarily sensitive things. They may have access to the CEO's inbox. Their calendar. Confidential company information. Board communications. Compensation information. Personal travel. Family information. Credit cards. Passwords. Sometimes virtually every logistical detail of an executive's professional and personal life.

We trust them to exercise judgment about what the CEO needs to know, who gets access, what is urgent, and what can wait. If we trust someone with all of that, we should probably be able to trust them to determine whether they can effectively work from home on a Wednesday when their executive is in Singapore.

You Get What You Give

At its best, the Executive Assistant–executive relationship is an extraordinary professional partnership. The EA gives the executive something incredibly valuable: flexibility.

They absorb change. They adapt. They rearrange. They anticipate. They respond. They make complicated lives run more smoothly. They answer a text on a Sunday, they move a meeting at 9pm. They come in early. They stay late. Perhaps they even travel across the country, or the world, with their leaders from time-to-time for important meetings. That doesn't mean executives should expect unlimited access to their assistants. Healthy boundaries still matter, and burnout benefits no one.

But when a role inherently asks someone to stretch beyond conventional working boundaries, the employer should be thoughtful about what they offer in return. The answer doesn't always need to be a formal hybrid schedule. Sometimes it is simply trust. Sometimes it is autonomy. Sometimes it is the ability to work from home when the executive is traveling. Sometimes it is saying, "You've got everything covered. Go."

The principle is remarkably simple: If you want exceptional flexibility from your Executive Assistant, give exceptional flexibility back.

Because the best executive partnerships aren't built by counting hours in chairs. They're built on trust, judgment, responsiveness, reciprocity—and a shared understanding that both people are ultimately working toward the same thing: making the executive, and the organization around them, more effective.

Three Ways to Explore EA-Hybrid Schedules (when company policy doesn’t govern):

1. When the Executive Is Away, the EA Can Be Away Too

One of the simplest approaches is to allow the EA to work remotely when the executive they support is not in the office - whether they are traveling, on PTO, working remotely themselves, or out sick.

Of course, this should always be subject to the needs of the business. If there is an important leadership meeting, company event, board meeting, or another responsibility that genuinely requires the EA’s physical presence, they come in. But if the primary reason they are in the office is to support an executive who is currently 2,000 miles away, it may be worth asking what is actually gained by requiring them to sit at their desk simply because everyone else does.

For many senior EAs, some of their busiest days are actually when their executive is traveling. They may be managing changing itineraries, coordinating across time zones, rearranging meetings, communicating with drivers and hotels, and troubleshooting in real time. If all of that work can be done exceptionally well from home, allowing them to do so can be an easy and meaningful form of flexibility.

2. Give Them a Bank of Flexibility - Not a Weekly Hybrid Schedule

Flexibility does not necessarily have to mean “You work from home every Tuesday and Thursday.” In fact, for a senior EA, that kind of rigid hybrid schedule may not make much sense at all.

Instead, consider allowing a trusted EA to work remotely for a reasonable percentage of the year (say 15-25% for instance), used when it makes sense for both the employee and the business. There does not need to be an elaborate policy governing every instance. The EA and executive simply communicate, look at the calendar, and make the call.

For example, an EA may want to spend two weeks visiting aging parents without using two full weeks of PTO. They have a dedicated workspace, reliable Wi-Fi, and can remain online and fully available during normal working hours. Their executive’s calendar is relatively quiet, with no major in-person meetings, board obligations, or events requiring their presence, and there is other support in the office that can lend a hand with the occasional physical task—getting a signature, receiving a delivery, coordinating lunch, etc. In a scenario like this, allowing the EA to work remotely for those two weeks can give them meaningful personal flexibility without meaningfully impacting the executive or the business. If there is another capable team member in the office who can occasionally help with something inherently physical—a signature, receiving a delivery, setting out lunch—perhaps the answer is yes on things like this.

For an exceptional, long-term EA, flexibility can become a form of currency that costs the organization very little but may be enormously valuable to the employee. If you can give a great person more freedom without sacrificing performance, responsiveness, or business needs, there is often very little downside.

3. Think in Hours, Not Just Full Remote Days

Flexibility also doesn't have to mean working from home for an entire day. Sometimes the most appropriate arrangement is simply allowing a trusted EA to flex their hours in recognition of the way the job actually works.

If your EA was online until 10:30 p.m. handling urgent matter for you being the entire morning changes (flight delays, cancelled meetings in New York while traveling, presentation updates, etc.), perhaps business needs allow them to arrive at noon the following day instead of 9:00 a.m. If they stayed late Wednesday night managing a company event, perhaps they quietly leave at 2:00 p.m. on Friday. If they handled an urgent flight change from their couch on Sunday morning, perhaps nobody needs to scrutinize the hour they step away for a longer lunch appointment later that week. This doesn't need to become a transactional exercise in which every after-hours email earns an hour back. That would defeat the purpose. It is simply an acknowledgment that senior executive support rarely fits neatly into a 9-to-5 box—and flexibility can work in both directions.

The best senior EAs understand when the job requires them to lean in. Great executives and companies understand when they can give some of that flexibility back. Ultimately, this is about trust, retention, and reciprocity. When you give a senior, proven EA reasonable autonomy over where and when they work, you are far more likely to retain them—and, in our experience, far more likely to get that same flexibility in return when the business demands it. The person who feels trusted and valued is often the same person who willingly answers the 9:00 p.m. text, handles the Sunday flight change, stays late when something goes sideways, or rearranges their own plans because their executive needs them.

And it comes back to the fundamental point: their job is not like everyone else’s. Their hours are often different. Their access is different. Their relationship with leadership is different. The expectations placed on them are different. So it makes sense that their flexibility—and even their career growth, compensation, and working arrangement—may look different too.

The goal isn’t to create special treatment for the sake of special treatment. It is to recognize a uniquely demanding role for what it is, build trust accordingly, and create the kind of partnership that makes an exceptional EA want to stay for years.

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