From Executive Assistant to Chief of Staff (Stay? Grow? Or Pivot?) | Webinar Notes from Nova Chief of Staff
Detailed notes from a webinar Offsite sponsored for 1000+ Executive Assistants
Yesterday, Offsite sponsored "EA to Chief of Staff: Stay, Grow, or Pivot?", whcih brought together Maggie Olson, Kristina Willis, and Becky Kaapuni.
They shared their experiences and insights on navigating career growth, understanding the distinctions between Executive Assistant (EA) and Chief of Staff (CoS) roles, and making informed decisions about career progression.
I thought the conversation was so valuable to Executive Assistants and Chiefs of Staff (two of the most popular titles we work with on a daily basis with our clients), that I created about 6 pages of notes that I shared as a PDF on LinkedIn and wanted to share with you, our valued reader of The Offsite Blog :).
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Meet the Speakers
Maggie Olson
Maggie Olson is the founder of Nova Chief of Staff, a premier destination for Chief of Staff education and development. With 20 years of experience leading large teams, Maggie has focused on enhancing both customer and employee experiences at companies including T-Mobile, Nordstrom, and Starbucks.
Notably, she became the first Chief of Staff to a president at a Fortune 40 company, leading a multibillion-dollar business with over 5,000 employees. In this role, she built the president’s Chief of Staff model from the ground up. Currently, Maggie operates the Nova Chief of Staff Certification course and serves as a fractional Chief of Staff, assisting mission-driven startup founders in scaling their businesses.
Kristina Willis
Kristina Willis is the Head of Customer Success at ShareCal, a software company revolutionizing time management and scheduling for assistants. Prior to joining ShareCal, Kristina spent four years at We Are Rosie, where she successfully transitioned from EA to Chief of Staff.
With experience supporting founders and C-suite executives, Kristina is an advocate and mentor for the administrative profession, emphasizing that there's no such thing as being "just" an EA. In 2022, she was honored in The Adweek 50, recognizing media, marketing, and tech's indispensable behind-the-scenes stars.
Becky Kaapuni
Becky Kaapuni is a career EA with over two decades of experience navigating the C-suite at companies including Salesforce, Twitter, and Goldman Sachs. She is a fierce advocate for Executive Assistants and leads the EA Revolution, aiming to unlock the vast untapped potential within every EA.
Through the EA Social Club and her book "The Unstoppable EA," Becky transforms how EAs perceive themselves, providing dynamic community, mentoring, and advocacy to reshape the profession.
Webinar Overview
The discussion provided attendees with practical advice on navigating career growth, understanding the real differences between EA and CoS roles beyond just the title, and insights into why some EAs choose to stay in their roles while others transition.
The panel also explored how EAs and Chiefs of Staff can create an unstoppable partnership in a CEO’s back office. This comprehensive conversation aimed to equip executive assistants considering their next career move, Chiefs of Staff refining their roles, and executives looking to maximize their support teams with the knowledge to make informed decisions about staying, growing, or pivoting in their careers.
Key Takeaways
Understanding Role Differences: Clarified the distinctions between EA and CoS roles, emphasizing that the difference goes beyond just the title.
Career Growth Insights: Shared experiences on why some EAs choose to stay in their roles, why some transition, and what that pivot can look like.
Self-Advocacy: Provided practical advice on navigating career growth and advocating for oneself in the workplace.
Authenticity in Roles: Discussed the power of authenticity and how to thrive in the role that fits best.
EA and CoS Partnership: Explored how EAs and Chiefs of Staff can create an unstoppable partnership in a CEO’s back office.
This webinar was ideal for executive assistants considering their next career move, Chiefs of Staff refining their roles and responsibilities, and executives looking to maximize their support teams.
The Journey from EA to Chief of Staff
1. Understanding the EA Role
Many professionals start as Executive Assistants, a role that involves:
Calendar Management – Ensuring the executive’s time is structured efficiently.
Travel & Logistics – Booking flights, hotels, and managing schedules.
Inbox & Communication Management – Filtering and prioritizing emails.
Personal Support – Handling non-business tasks to streamline executive efficiency.
Tactical Problem-Solving – Proactively identifying and addressing scheduling and operational challenges.
2. When an EA Evolves into a Chief of Staff
As EAs gain exposure to broader business functions, they may naturally take on more strategic responsibilities, including:
Cross-functional collaboration with leadership teams
Driving strategic initiatives that don't fit neatly into existing roles
Facilitating communication and alignment between executives and teams
Managing special projects and key business priorities
3. Key Indicators That You're Ready to Move into a CoS Role
Shifting Priorities: You’re more focused on the executive’s goals than their immediate needs.
Project Ownership: You’re managing cross-functional initiatives beyond administrative tasks.
Strategic Thinking: You’re providing recommendations, not just executing tasks.
Desire for Impact: You want to influence the business at a higher level rather than focusing solely on supporting an individual executive.
The Core Responsibilities of a Chief of Staff
While the EA role is deeply tied to supporting an individual, a Chief of Staff’s scope expands to supporting the executive’s strategic objectives and broader business operations.
Key Responsibilities of a Chief of Staff:
Strategic Execution – Driving initiatives that align with company goals.
Leadership Team Alignment – Ensuring transparency and communication across executive teams.
Special Projects & Business Operations – Leading high-priority efforts that require executive oversight.
Problem Solving & Decision Support – Providing analytical insights and recommendations to senior leaders.
Managing Board & Investor Communications – Coordinating reporting and strategic discussions at the highest level.
Differences Between EA and Chief of Staff
The Mindset Shift from EA to Chief of Staff
1. From Managing an Executive to Managing Business Priorities
One of the biggest mindset shifts when transitioning to a Chief of Staff is focusing on the executive’s goals rather than the executive themselves.
EA: Ensures the executive’s day runs smoothly.
CoS: Ensures the executive’s strategic objectives are executed efficiently.
2. From Support Role to Leadership Role
EA: Provides logistical support for leaders.
CoS: Acts as a trusted strategic partner in decision-making.
3. Influence Over Direct Authority
Unlike traditional leadership roles, Chiefs of Staff often operate through influential leadership, guiding teams without direct managerial authority.
Advocating for the Chief of Staff Role
For those looking to transition into a Chief of Staff role, advocacy is crucial.
Steps to Advocate for the Chief of Staff Role:
Identify Gaps in Your Organization – Determine where a CoS could add value.
Document Your Current Responsibilities – Highlight tasks that already align with CoS duties.
Create a Roadmap for the Role – Define milestones and strategic objectives to transition successfully.
Pitch the Business Case to Leadership – Showcase how a Chief of Staff role will help the organization scale.
Salary and Career Growth
A common misconception is that moving from EA to Chief of Staff automatically results in higher pay. However, many senior EAs earn as much or more than some Chiefs of Staff.
Key Considerations for Compensation Growth:
Research Salary Benchmarks – Look into industry compensation trends for both roles.
Negotiate Based on Impact – Position yourself as a value-add to the organization.
Alternative Growth Paths – Consider adjacent roles in operations, strategy, or business leadership.
Final Thoughts
The transition from EA to Chief of Staff isn’t just a job change—it’s a strategic career evolution.
For EAs who love supporting an executive personally and operationally, staying in the EA role can be a fulfilling and lucrative career path.
However, for those who want to drive business strategy and company-wide initiatives, the Chief of Staff role offers an exciting and impactful opportunity.
Whether you’re an Executive Assistant or Chief of Staff, the friendly folks at Offsite can save you time, money, and stress when planning team retreats.
Make a free account at Offsite.com today and see why hundreds of companies trust us to plan their offsites around the world. Or email jared@offsite.com to set up a discovery call.