Here’s something for you to think about this week: Why are Executive Assistants often expected to flex “up”, but Chiefs of Staff are never asked (and in fact, are usually encouraged not) to flex “down”? 

I mean, we hear it all the time: Chiefs of Staff (CoS) are “strategic” and “operational leaders,” while Executive Assistants (EAs)—or Executive Business Partners, Executive Personal Assistants, whatever the title—are primarily responsible for handling administrative and logistical tasks. 

But the reality is, Executive Assistants almost always end up flexing “up” into responsibilities like strategy, operations, project management, and communication, traditionally reserved for Chiefs of Staff. Meanwhile, it’s rare—if ever—that a Chief of Staff is asked to “flex down” and take on the logistical or day-to-day duties of an EA. Why is that?

It’s an interesting and somewhat problematic dynamic when you think about it. EAs are expected to stretch into higher-level roles, constantly proving their adaptability and range. Chiefs of Staff, on the other hand, are given a hard line between their “strategic” or project management duties and anything resembling administrative work. This raises a crucial question: Why are EAs constantly being asked to expand their scope, while Chiefs of Staff are shielded from tasks considered “beneath” them?

Note: I understand that this does not apply to all Chiefs of Staff, however, there is a lot of rhetoric in the professional space right now that proclaims Chiefs of Staff should NEVER engage in administrative or day-to-day work. I’m just saying, we should question that! 

Is it back to a conversation of value? Or a lack of understanding about the Executive Assistant (and the Chief of Staff) role? If so, let’s change that narrative once and for all. 

Executive Assistants Constantly Flex “Up”

Let’s break this down: EAs are consistently stepping into areas that are often considered the exclusive domain of Chiefs of Staff. They’re handling operations, managing large projects, contributing to high-level strategy, and taking on leadership roles—often without a formal title change or corresponding compensation increase. In fact, many EAs end up functioning like Chiefs of Staff without the recognition. Yet, we rarely see a Chief of Staff handle anything that resembles the administrative responsibilities EAs typically manage. 

Again, why is that? Is there more clarity around the Chief of Staff role? Therefore it’s easier to uphold boundaries? Is it because usually a Chief of Staff comes in after an Executive Assistant is on staff, therefore those day to day responsibilities are already handled? Whereas before a Chief of Staff is hired, very often the EA take on the more immediate Chief of Staff responsibilities as well? 

This discrepancy (if there is one) around value is puzzling, given how much overlap exists between the two roles in certain contexts and companies. Sure, when all things are equal and an organization is large or a leader’s life complex enough, a Chief of Staff and an Executive Assistant both exist and operate in two distinct roles. 

But, more often than not, it’s a leader and an Executive Assistant first who grow, lead, and flex TOGETHER, long before a Chief of Staff ever steps on the scene. 

My Experience From Executive Assistant to Chief of Staff (and Beyond)

Obviously, this hits close to home for me. As an Executive Assistant, I regularly expanded my scope of work, taking on more strategic tasks. And then I flexed my way into developing the Chief of Staff role at our company and promoting myself into the position. Over time, I often served as a de facto VP, as well as co-creator of several projects and co-founder of a company. I didn’t stop at supporting the executive—I became an integral part of the leadership, working side by side with my executive to build something meaningful.

In this evolution, I found that the most successful partnerships come when both the EA and the executive grow and flex together. It’s often in these dynamic relationships that an EA is able to prove their value as more than just someone who handles logistics. They become the trusted partner, the person who knows the leader’s priorities inside and out, can navigate change, lead up, and turn ideas into action. 

Again, this doesn’t mean that Chiefs of Staff aren’t valuable team members. Rather, I just want to remind everyone that Executive Assistants are too (with or without a Chief of Staff on staff). 

Executive Assistant to CEO to Chief of Staff Ratio

While we definitely have to take these stats with a grain of salt (i.e. not all of LinkedIn profiles are accurate or up to date), I still think they are interesting to take a look at. According to a LinkedIn search, there are 563,000 people with the title Chief of Staff in their profile and over 6.5 million Executive Assistants. Meanwhile, there are nearly 10 million people with CEO and founder in their profile.

This indicates a few things to me. First, the Chief of Staff role is still relatively new to the corporate scene (though clearly growing in popularity). 

Second, when it comes to finding a true “right hand” partner for a power player—whether that’s a founder, CEO, or other top executive—it’s far more likely that role will be filled by an EA than a Chief of Staff. After all, not every organization is large enough or a leader’s life complex enough to justify both an EA and a Chief of Staff. But you can bet that almost every leader needs an EA, and when that EA is properly scoped, the value they provide is immeasurable.

The Reality: Flexibility and Adaptability Are Key

Executive Assistants are quickly embracing AI and often outsourcing traditional administrative functions such as calendar management, scheduling, and communication management to technology, allowing them to “flex up” to what’s being demarcated as Chief of Staff work. At the same time, we’re telling Chiefs of Staff to never handle EA tasks. This perpetuates the narrative that “strategy” work is somehow more valuable than the “day-to-day” tasks that keep an executive functioning. But ask any executive who’s had an outstanding EA: they’ll tell you that having someone who can manage both sides of the equation is invaluable.

Personally (from an entrepreneur and small business lens) I’d rather have someone highly flexible and adaptable on my team, then one who only handles “strategy”. 

This is why I return to the idea of the Force Multiplier—a title that captures the essence of what both EAs and Chiefs of Staff can be. It’s not black and white. There are too many variables. The Chief of Staff and Executive Assistant/Executive Business Partner roles are both incredible roles and career paths with lots of opportunity. 

But making yourself invaluable as a right hand partner… shouldn’t that matter more than constantly talking about what you “should and shouldn’t do?” I have always believed that if you do exceptional work, provide value to your Executive and company, and advocate for yourself if/when needed, the money will follow. But the respect will only come if you do the aforementioned. 

I will continue to champion those who are doing great work helping with universal titling, compensation, and re-leveling across these roles. 

Meanwhile, I’ll be over here focused on my mission of helping entrepreneurs and leaders find the right right-hand partner, build strong strategic partnerships, and build wildly successful businesses and careers along the way, regardless of title. Whether that’s as an Executive Assistant, Chief of Staff, Founder’s Associate, Operations Manager, Personal Assistant, Officer Manager, or some other Force Multiplier position, the goal remains the same: ensuring the objectives, goals, and vision of the Executive are organized, communicated, delegated, and executed.