Maggie Olson

Chief of Staff vs. Executive Assistant… 
  
What’s the difference? 
  
At first glance, the roles of Chief of Staff and Executive Assistant may sound similar. 
  
Both support the leader. 
Both are crucial to a team’s success. 
Both are positioned in the leader's back office. 
  
**But make no mistake... 
  
They are very different positions, each with its own unique scope and impact. 
  
Here’s a breakdown of the key differences between the two: 
  
🔑 Strategic Leadership 
  
CoS: Leads high-level strategic projects that shape the direction of the business.  
  
EA: Primarily focuses on supporting day-to-day operations & logistics. 
  
🔑 Extension of the Leader 
  
CoS: Acts as a direct extension of the leader, often making high-level decisions on their behalf and ensuring alignment of the team. 
  
EA: Leads all aspects of logistical needs but generally doesn’t step into high-level decision-making scenarios. 
  
🔑 Business Impact 
  
CoS: Works both on the business (strategy and leadership) and in the business (operations, execution).  
  
EA: Primarily focuses on business impact of day-to-day administrative support, assisting the leader with impact and efficiency. 
  
🔑 Cross-Functional Leadership 
  
CoS: Leads cross-functional teams and oversees the execution of key initiatives across the company.  
  
EA: Supports tasks across different teams but doesn't usually lead major cross-company initiatives.  
  
🔑 Ownership of Major Initiatives 
  
CoS: Owns the leader's most important projects, ensuring they are carried through to execution, monitored, and shared broadly. 
  
EA: May assist with many components of key initiatives but doesn’t usually own them or drive them to completion.
  
🔑 Vision Cascading
  
CoS: Deeply learns and understands the leader’s vision and cascades it throughout the company, ensuring everyone is aligned.
  
EA: Assists in sharing the leader’s vision, but isn’t usually fully responsible for communicating or executing the vision across the company.
  
🔑 Proactive Problem Solving
  
CoS: Proactively dives into various areas of the business, identifying problems and crafting solutions for major company issues.
  
EA: EAs are proactive in nature, but they are not typically responsible for solving business-wide challenges.
  
— 
  
While a great EA may step into some of these areas, the Chief of Staff role is distinct.
  
It’s a leadership position focused on driving change, leading teams, and executing high-level strategy.
  
**So, ask yourself...
  
- Are you ready to lead the company’s most critical initiatives?  
- Run your team's back office and rhythm of business?  
- Act as a strategic partner to your leader?
- And drive major alignment across the executive team?
 
Then you're ready for Chief of Staff.
  
PS. Leaders: If the Chief of Staff list describes your EA, promote them.
  
♻ Share to help spread awareness of the Chief of Staff and EA roles.
  
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EA: “I’m not sure I’m a leader.”

Let’s be clear, you are.

EAs are some of the *most influential* leaders in an organization.

👍 Anticipating needs 
👍 Managing priorities 
👍 Incredibly trusted by senior leaders 
👍 Navigating complex relationships & politics 
👍 Being the eyes & ears of the org for your leader…

I consider EAs incredibly influential.

And I've looked up to EAs throughout my career.

But too many EAs don’t recognize how transferable and valuable these skills can be at the next level.

If you're an EA who's ever questioned whether you're a leader, take a closer look at what you already do day-to-day.

I’d challenge you to look at your problem-solving, your breadth of responsibility, and your understanding of complex relationships across the company.

You are ALREADY leading.

It's time you OWN IT.

In the comments: EAs, how do you articulate your value? 
 
♻️ Share to help spread Chief of Staff awareness. 
👋 Follow Maggie Olson for daily CoS & leadership insights.

Most people think becoming a Chief of Staff is about WHERE you came from. 
 
Your title, your degree, your industry background. 
 
But here's the thing… it's not. 
 
It's about HOW you show up. 
 
I see this often, people with "impressive" resumes who struggle in the CoS seat and people with unconventional paths who THRIVE. 
 
Because the CoS role doesn't care about your resume as much as it cares about your wiring. 
 
 
These are the traits that help you thrive in the role. 
 
🌟 Agility: You're always change-ready 
 
🌟Deeply Curious: You seek to understand, never assume 
 
🌟Observant: You spot patterns and trends 
 
🌟Emotionally Intelligent: You build rapport with the right stakeholders 
 
🌟Collaborative: You act from a “we,” not a “me” mindset 
 
🌟Comfortable Behind the Scenes: No need for praise or accolades 
 
🌟 Brave: You're willing to speak truth, and skilled in how to say it 
 
🌟Inspiring: You help others shine brighter and grow 
 
 
And in practice, a great CoS is: 
 
→ Ensuring the right conversations happen at the right time 
 
→ Walking into every meeting informed and confident 
 
→ Pulling the leader out of the weeds 
 
→ Solving, stabilizing, improving, and handing off 
 
→ Listening, observing, and connecting dots 
 
 
The role isn't for everyone… 
 
But if this sounds like you, it just might be for you. 
 
In the comments: Which trait on this list is your biggest strength? Which one are you still developing? 
 
 
♻️ Share this if you know someone who leads from behind the scenes but deserves to know the CoS role exists. 
 
👋 Follow Maggie Olson for daily insights on the CoS & EA world.

Most people think becoming a Chief of Staff is about WHERE you came from.   
  
Your title, your degree, your industry background.   
  
But here's the thing… it's not.   
  
It's about HOW you show up.   
  
I see this often, people with "impressive" resumes who struggle in the CoS seat and people with unconventional paths who THRIVE.   
  
Because the CoS role doesn't care about your resume as much as it cares about your wiring.   
  
These are the traits that help you thrive in the role.   
  
🌟 Agility: You're always change-ready   
  
🌟Deeply Curious: You seek to understand, never assume   
  
🌟Observant: You spot patterns and trends   
  
🌟Emotionally Intelligent: You build rapport with the right stakeholders   
  
🌟Collaborative: You act from a “we,” not a “me” mindset   
  
🌟Comfortable Behind the Scenes: No need for praise or accolades   
  
🌟 Brave: You're willing to speak truth, and skilled in how to say it   
  
🌟Inspiring: You help others shine brighter and grow   
  
  
And in practice, a great CoS is:   
  
→ Ensuring the right conversations happen at the right time   
  
→ Walking into every meeting informed and confident   
  
→ Pulling the leader out of the weeds   
  
→ Solving, stabilizing, improving, and handing off   
  
→ Listening, observing, and connecting dots   
  
  
The role isn't for everyone…   
  
But if this sounds like you, it just might be for you.   
  
In the comments: Which trait on this list is your biggest strength? Which one are you still developing?   
  
  
♻️ Share this if you know someone who leads from behind the scenes but deserves to know the CoS role exists.   
  
👋 Follow Maggie Olson for daily insights on the CoS & EA world.

The Chief of Staff role is one of the most misunderstood in business.

The vague title doesn’t help, nor does the fact that many people are doing the work of CoS under a completely different title.

Think Biz Ops, Business Planning, Strategic Planning, or Executive Business Partner, to name a few.

So, let’s clear things up.

Here’s a breakdown of three roles most commonly confused with Chief of Staff: 
 
💼 Chief of Staff Definition

The strategic right hand to a business leader focused on execution, alignment, and driving key initiatives.

Prioritizes what matters, ensures transparency across the leadership team, and turns vision into action.  
 
💼 Executive Assistant 

A logistical powerhouse managing calendars, travel, expenses, and tactical support. 

Keeps the executive on track and operations running smoothly. 

→ Confusion Level: 4/5 

→ Cheat Code: EA = tactical partner, CoS = strategic partner  
 
💼 Chief Operating Officer 

Owns the operational backbone of the business, ensuring scalability, efficiency, and execution of company-wide initiatives. 

Manages teams, oversees processes, and drives performance. 

→ Confusion Level: 3/5 

→ Cheat Code: COO = supports business, CoS = supports leader  
 
💼 HR Executive 

Leads hiring, employee relations, culture, and training. 

Ensures policies align with company goals and support a thriving workforce. 

→ Confusion Level: 2/5 

→ Cheat Code: HR = company's people, CoS = business leader's initiatives 
 
The CoS role is unique because it adapts to the leader's needs and exists FOR the leader. 

It’s not just about culture, operations, execution, or strategy—it’s all four… and more. 

As the Chief of Staff role gains traction, understanding matters.

So let’s set the record straight: 

A Chief of Staff is a business leader’s strategic, execution-focused partner—turning vision into reality.  
 
♻️👋 Engage, share & follow Maggie to support this post.

Six years ago I was a consistent high performer.

Leaders wanted me on their teams, I was getting promoted, and I had excellent reviews with my leaders.

By every external measure I was doing well!

But I couldn’t articulate my own value, like AT ALL.

- I didn’t know what I was good at
- I didn’t know what roles I should go after
- I didn’t know how my skillset translated
- I didn’t know what would actually fulfill me

I was doing a great job in the roles I was in… but that never felt like enough. It was never really *intentional.*

How could I be such a high-performer but have no idea how to figure out what was next? What was perfect for me?

Total mismatch.

This completely changed when I discovered the Chief of Staff role.

It was the first time I was in a role that made total sense for the person I actually was:

- someone great at a lot of things
- who executives trust to get big things done
- and who thrives in the space between strategy, execution, collaboration, and problem-solving.

Finding the Chief of Staff role gave me direction and confidence I didn’t know I was missing.

Since then my mission has been to help people who are exactly where I was:

the high achievers and strategic operators who know they’re meant for way more but don’t really know how to name what makes them exceptional (hi, it’s you 😇).

Building a brand on LinkedIn connects to the same idea.

Whether you’re posting daily to build a brand (like I started to do 3 years ago) or posting weekly to stay credible to recruiters… both really matter (like really, matter).

*It’s how the right people find you before you even know they’re looking.*

I post to:

- spread Chief of Staff awareness
- help others unlock their potential
- build credibility & ensure people know me
- build business relationships & partnerships
- elevate the CoS space as a whole

So glad you’re here!

Why are you posting? Introduce yourself below and lmk if you have Qs about my path on LinkedIn.


♻️ 👋 Follow Maggie Olson for daily CoS and LinkedIn content.

📸 2019

With quick advancements in AI, the EA role is changing fast.

So what's the reality?

Executive Assistants are one of the most strategically positioned roles in any organization. Meaning: EAs are well suited to keep up. 👏

But it's non-negotiable that EAs MUST level up or they will get left behind.

So where do you start?

I just finished filming a 12-part series breaking down what it truly means to be a STRATEGIC Executive Assistant.

👇 Comment VIDEOS for the link. 👇

Short form, easily digestible, and completely free.

I'm covering everything I wish EAs and Chiefs of Staff everywhere knew about themselves, their role, and how to add tangible strategic value right away.

This is how I teach "EA to CoS" live, all in one spot... for the first time ever.
💕
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👇 Comment VIDEOS & hit repost for the link
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