The role of an Executive Assistant (EA) has transformed beyond calendar management and administrative tasks. Today’s top EAs act as strategic partners, problem-solvers, and key advisors to executives. Naturally, many ambitious EAs are setting their sights on a bigger role—the Chief of Staff (CoS).
If you're ready to level up, transition into a leadership-driven role, and have a bigger impact on your organisation, this guide will help you navigate the journey from EA to Chief of Staff with confidence.
Why Make the Move?
Shifting from EA to CoS isn’t just a step up—it’s a whole new ballgame. Here’s why this transition is worth considering:
- More Strategic Influence – Instead of supporting leadership, you’ll be shaping it. A CoS works closely with executives on high-impact decisions.
- Career Acceleration – Becoming a Chief of Staff is a natural stepping stone to future leadership roles, even including CEO positions.
- Expanded Responsibilities – Move from managing tasks to driving business strategy, overseeing cross-functional projects, and influencing company-wide initiatives.
What Skills Do You Need to Become a Chief of Staff?
Making the leap from EA to Chief of Staff requires a shift in mindset and skill set. Here’s what you need to master:
1. Strategic Thinking
You’ll need to think big picture—analysing business challenges, identifying opportunities, and advising executives on critical decisions.
2. Project & Operations Management
CoS roles involve overseeing key projects and ensuring teams align with company goals.
3. Leadership & Influence
Unlike an EA, a CoS leads teams, drives change, and serves as the CEO’s right hand. Strong leadership and stakeholder management skills are essential.
4. Financial & Business Acumen
Understanding budgets, forecasting, and high-level business strategy will make you a valuable advisor in the boardroom. Consider learning financial modelling or business analytics.
5. Communication & Executive Presence
As a CoS, you’ll interact with senior leaders, board members, and key stakeholders—your ability to communicate with confidence and clarity is critical.
Your Roadmap: How to Transition from EA to Chief of Staff
Step 1: Develop a Strategic Mindset
- Shift from executing tasks to proactively solving business challenges
- Stay informed on industry trends, company strategy, and competitor insights
- Join high-level discussions with executives whenever possible
Step 2: Expand Your Skill Set
- Take courses on business strategy, finance, and leadership (Check out Harvard Business Review, Coursera, or LinkedIn Learning)
- Learn data analysis and budgeting—essential skills for decision-making
- Seek mentorship from Chiefs of Staff and senior executives
Step 3: Gain Leadership Experience in Your Current Role
- Offer to lead cross-functional projects beyond administrative work
- Take on strategic planning responsibilities within your company
- Shadow executives to understand decision-making at a high level
Step 4: Build a Strong Professional Network
- Attend industry events, leadership summits, and CoS networking groups
- Join Chief of Staff associations (e.g., Chief of Staff Association, Base HQ)
- Connect with professionals who have successfully made the EA-to-CoS transition
Step 5: Position Yourself for the Promotion
- Clearly communicate your career aspirations to your boss
- Showcase leadership, initiative, and a strategic mindset
- Go beyond administrative support—demonstrate your ability to drive business impact
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Overcoming Challenges in the Transition
Imposter Syndrome?
Confidence comes with preparation—keep learning, seek mentorship, and trust your capabilities.
Lack of Strategic Experience?
Start small—volunteer for strategic initiatives and work closely with leadership.
Leadership Resistance?
Proactively demonstrate your readiness by taking on more responsibilities and driving impact.
Can EAs Become CEOs? It’s Happened Before!
While the Chief of Staff role is a natural next step, some ambitious EAs have climbed even higher—to the CEO seat.
- Ursula Burns – Former CEO of Xerox
Burns started at Xerox as an intern before becoming Executive Assistant to the CEO. Her time as an EA gave her deep insight into the company’s strategy, eventually leading her to become the first African-American woman to lead a Fortune 500 company. - Victoria Darragh – CEO, Executive & Personal Assistants Association (EPAA)
Darragh’s experience as an EA helped her build a strong leadership foundation, ultimately allowing her to lead an entire professional organisation dedicated to Executive Assistants.
Your Future as a Chief of Staff Could Start Now
Making the transition from Executive Assistant to Chief of Staff isn’t just about getting a new title—it’s about elevating your career, expanding your influence, and shaping the future of your organisation.
By upskilling, gaining leadership experience, and strategically positioning yourself, you can successfully step into the CoS role—and beyond.
The future of your career is in your hands—take the first step today!
Knightsbridge Recruitment is a boutique consultancy which has been placing stand-out candidates in the most sought after permanent, temporary and part-time Chief of Staff, Executive Assistant, Personal Assistant, Private PA and executive office support jobs in London, for over 35 years. If you would like advice on hiring and retaining exceptional staff, or would like to discuss your next career move, we would love to help - please call us.
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