EA vs Chief of Staff

Forward-thinking principals don’t choose between an Executive Assistant and a CoS. They build with both.

The Mislabeled Chief of Staff

I’ve read hundreds of Chief of Staff job descriptions. After a while, patterns emerge. Some make sense but others made me tilt my head and audibly say, huh 🤔?

There was one job in particular that I still think about. The company was exciting but the principal impressed me most. She’d built something meaningful over the course of her entire career at the same company, growing in the ranks all the way to President. In interviews she was grounded, thoughtful and kind of a badass. I’d listened to several podcasts featuring her and thought, she’s the kind of leader I’d want to support.

But then I read the job description.

It was listed as a Chief of Staff role but there were a few bullets that gave pause. Things like “order catering for leadership meetings” and “calendar management.” Perfectly reasonable tasks, just not for a Chief of Staff.

So I mailed her a letter (with a Stamp by my friend Antonio of course). I shared my admiration for her work and gently pointed out the difference between an EA and a CoS. I sent her a copy of Who Has Your Back by my coach, Laurie Arron, with a few pages bookmarked for easy reference.

I never heard back. But a week later, the job title was updated to Senior Executive Assistant.

I was tickled. Obviously it was my letter 💁‍♀️.

The experience clarified something I’ve seen over and over again: people confuse these two roles all the time. But they’re not interchangeable.

A busy principal with a vision and a big mission on the horizon needs both.

The Framework: right hand vs left hand

The Executive Assistant and the Chief of Staff are the principal’s left and right hands. It’s not an either or situation because the answer is yes, both. They work in sync while serving different goals and creating different types of leverage.

The Chief of Staff is the right hand: strategic, trusted, connected with teams and embedded in decisions before they happen. The Executive Assistant is the left hand: also high trust, precise, passionate about details, anticipatory but most importantly ensures the machine keeps running.

One clears the mental clutter. The other clears the calendar. Together they magically add hours to your day.

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Why the roles get blurred

The confusion always starts with the Chief of Staff not the Executive Assistant. The EA role has been around longer and thus is more clearly defined, while under appreciated. But the CoS? That’s still misunderstood.

I was just talking to Laurie about this, how the Chief role is very bespoke. It’s designed around the principal, not a fixed job description. And because both roles sit close to the principal it’s easy to blur the lines. It’s not one size fits all.

Adding to the confusion, great CoS work is often invisible. At COS 25, I asked a few Chiefs how they benchmark success. The most common answer?

“If everything’s running smoothly without issue, I’m doing my job.”

When that kind of value is hard to quantify, people default to what they can see: tasks and tangible outcomes. Then if a job description is just a list of tasks, it’s easy to get the role wrong.

Add in a few other factors like title inflation, cost-saving instincts, or a principal who’s never had a true CoS, and you’ve got the perfect recipe for confusion.

These are the three most common mistakes I’ve seen:

• Trying to hire both roles into one person signals a lack of clarity around what the CoS is actually for.

• Labeling an EA job as a CoS role can happen when someone wants to make the role sound more important or hasn’t thought it through.

• Assuming the CoS is a junior executive or a “mini-me” leads to misalignment and role tension.

None of this is malicious. Most of the time, it’s just a lack of shared language about what these roles really do.

When you define them clearly, everything gets easier.

How to know you need both

When you don’t have both a Chief of Staff and an Executive Assistant, things break down quietly at first, then all at once.

From a principal’s lens, here are a few examples and what they really mean:

1. You’re stuck in decision loops

Symptom: Your team keeps circling back for clarification, just one more question. Priorities feel fuzzy. You’re answering the same questions over and over.
Root Cause: No one is owning decisions across work streams.
You need: A Chief of Staff to clarify direction, coordinate across functions and keep the trains running on what matters most.

2. Your calendar is logistically impossible

Symptom: You’re triple-booked, rescheduling meetings yourself and constantly running late or worse cancelling meetings.
Root Cause: No one is protecting your time with intention.
You need: An Executive Assistant to run point on logistics, anticipate conflicts and effortlessly organize the board.

3. Your EA is “running point” on strategic projects

Symptom: Your EA is managing initiatives outside their lane, chasing updates from leaders and making judgment calls without context.
Root Cause: The team is overloaded, roles are confused and because of that you’ve lost that strategic rhythm
You need: A Chief of Staff to own cross-functional alignment, manage meeting cadence that drives momentum.

4. Everything is urgent. Nothing is clear.

Symptom: You’re reacting to fires all day. No one’s filtering, prioritizing or thinking long-term.
Root Cause: You’re trying to operate without leverage.
You need: Both. An EA to manage execution and a CoS to manage complexity and then something like The Burn Filter to help triage what actually matters.

How an EA and a CoS work together

In a perfect world, the EA and Chief of Staff operate like Batman and Robin. Always in sync but behind the scenes.

They collaborate on the daily and weekly agenda, spot issues early, and when the relationship is strong, can practically finish each other’s sentences.

Here’s what that can look like in real life:

I’m out having coffee with a colleague who casually mentions a potential bottleneck on a major project. Alarms go off in my head but I remain clam. Because I know the priorities, it’s clear this could become a fire if we don’t address it now. I need to triage before it becomes a problem.

Back at the office, I give the EA a look. No words needed. She grabs her coat and we head out for a quick walk.

We come up with a plan. I’ll confirm some information and draft the triage strategy. She updates me on the principal’s schedule not just what’s on the calendar, but what’s actually happening behind the scenes over the next few days.

While I start working the issue, she quietly checks on status updates, makes a few subtle adjustments to the principal’s schedule and clears the way.

None of this touches the principal until there’s a clean plan to execute or a decision to be made.

That’s the magic of a well-synced EA+CoS duo. Calm coordination, invisible friction removal and the right things handled before they ever become a distraction.

So what now?

If you’re a principal considering one or ideally both roles, ask yourself:

• Do I need someone protecting my time?

• Do I need someone extending my thinking?

You don’t need to choose. You can have both.

Trying to combine these roles into one won’t save you time or money. It’ll cost you both. It leads to confusion, burnout and constant course correction.

If you’re a Chief of Staff stuck juggling catering orders or flight logistics, it’s time to demonstrate your leverage. Here’s how I’d start:

• Track the friction. For the next two weeks, document what you’re doing that an EA could own. Be specific with dates, tasks and context.

• Name the tradeoffs. Show where strategic work slipped because you were pulled into logistics. (e.g. “on 6/5/25: Spent 3 hours managing schedules instead of running triage on Project X then the team lost momentum.”)

• Model the opportunity. Take one week and assume you had an EA. What could they take off your plate? What would that free you up to do? Document it. I’d even share this with a few colleagues for their feedback.

• Write the role. Draft the EA job description and collaborate with the talent team to build it.

• Make the case. Once your plan is clear, bring it to your principal. This isn’t a big ask. Remember it’s a six-inch putt.

You’re not asking for help.
You’re building the system.
The one that makes everyone better, including your principal.

Two roles. Two lanes. One leadership system.

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P.S. I’m working on a customizable Chief of Staff job description template. With it you can optimize it to fit your company stage, leadership style and specific needs. If you want an early copy, shoot me a message and I’ll send you a copy.