Should I Hire an Executive Assistant or a Chief of Staff?
A practical guide for leaders who are doing too much
If you’ve ever looked at your calendar and thought, “I can’t keep running like this,” you’re in good company.There comes a point where the pressure just doesn’t let up.
That’s usually when this question surfaces:
Should I hire an Executive Assistant or a Chief of Staff?
Both are powerful roles. But they serve very different purposes. And choosing the right one can be the turning point between barely keeping up—and actually leading with clarity and confidence.
The Core Difference: Support for You vs. Support for the Business
Executive Assistant = Your personal strategic partner
A great EA is all about you. Your schedule. Your focus. Your ability to do the work only you can do. They handle the day-to-day so you can lift your head and lead.
They manage your calendar, inbox, travel, and follow-ups—but more importantly, they anticipate your needs, think like you, and make sure your week actually works for your life.
Picture this: You’ve got back-to-back meetings and zero breathing room. Your EA quietly clears space, shifts a few calls, preps your talking points, and sends thoughtful follow-ups. You end the day with energy left to take your kid to soccer instead of collapsing on the couch.
Chief of Staff = Your organizational operator
A CoS is built for the big picture. They’re your behind-the-scenes partner helping move strategy from idea to execution.
They work across departments, align teams, drive key projects, and act as your eyes and ears when you can’t be in every room. They help you lead at scale.
Picture this: Sales and Ops are at a standstill on a new initiative. Your CoS brings the right people together, uncovers what’s missing, and returns with a clear plan. You stay out of the weeds—but fully in the driver’s seat.
5 Questions to Help You Choose the Right Role
- Where’s the biggest friction in your work right now?
- Drowning in logistics and inbox clutter? → EA
- Stalled priorities and misaligned teams? → CoS
- Do you need time back—or leverage across the business?
- Time, space, and personal clarity → EA
- Organizational traction and influence → CoS
- Are you craving control of the details or momentum on the big stuff?
- Want your day to feel smoother? → EA
- Need the company to move faster, smarter? → CoS
- What kinds of decisions are you ready to let go of?
- Scheduling, communication, planning? → EA
- Prioritization, alignment, team strategy? → CoS
- What would feel different in 30 days with the right support?
- Could you take a real vacation? → EA
- Could you finally launch that long-stalled initiative? → CoS
What We’ve Seen From Hundreds of Leaders
This isn’t theory—it’s pattern recognition.
At Base, we’ve supported hundreds of executives through this exact decision. And here’s what we’ve seen:
- Others are stalled not because of bad strategy, but because they don’t have the time or clarity to execute it. Once they bring on the right EA, everything starts to move.
- Many leaders assume they need a Chief of Staff, when what they actually need is to breathe again. A sharp EA often resolves 80% of the chaos—quickly.
- The best CoS placements happen after an EA has already been in place—clearing the executive’s plate so they have the space to lead at the next level.
We’ve also seen leaders make the wrong hire and lose precious momentum. And it’s almost always because they hired for the role—not the need.
What the EAs and CoS in our network say
“While both roles support leadership, they serve different purposes. An Executive Assistant (EA) focuses on optimizing your time and ensuring daily operations run smoothly – managing your calendar, email, travel, meetings, and follow-up. A Chief of Staff (CoS) works at a more strategic level, helping drive cross-functional initiatives, align teams, and manage long-term priorities. If you need day-to-day support that frees you up to focus on high-impact work, an EA is often the most effective place to start.”
“If you are a CEO or C-Suite executive looking for a confidant and someone that can elevate further the strategy of the business you are looking for a Chief Of Staff. If you are looking to increase your personal and leadership team’s efficiency and capability, by removing a lot of operational and logistical tasks from their responsibilities you are looking for a strong Executive Assistant.”
“Start by looking at what’s slowing you down. If you’re constantly in the weeds, managing your calendar, drowning in emails, or juggling tasks someone else could do, an EA will bring immediate breathing room. If you’re already supported operationally but need help aligning people, projects, and priorities at a higher level, then a Chief of Staff might be the right move. Sometimes, starting with a strong EA can help clarify whether a CoS is genuinely needed, or if a skilled EA can grow with you into that next level of support.”
Let’s Be Honest: This Isn’t Just a Hiring Decision
It’s personal.
Choosing between an EA and a CoS isn’t just about what you need on paper. It’s about how you feel day to day. Overwhelmed? Reactive? Running on fumes?
That’s not a leadership problem—it’s a support structure problem. And fixing it doesn’t mean you’re failing. It means you’re human.
Leadership isn’t about doing it all. It’s about doing what only you can do—and building the right support around you.
Final Thought: You Deserve Support That Fits
Whether that starts with protecting your mornings or unblocking your org chart, the most important thing is this:
You don’t have to figure it out alone.
We’ve helped hundreds of leaders answer this exact question. We’d love to help you find support that actually sticks—and makes your life feel a little more human again.
