From Executive Assistant to Chief of Staff: How to Take the Step

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.

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