For Executive Assistants (EAs) with ambition beyond traditional support roles, the path to becoming a Chief of Staff (CoS) is a natural yet highly strategic career progression. This transition requires more than just experience – it demands a shift in mindset, expanded business acumen, and the ability to operate at a leadership level.
The Role of a Chief of Staff
A Chief of Staff serves as the executive’s right hand, overseeing strategic initiatives, managing key relationships, and driving organisational priorities. Unlike the EA role, which primarily focuses on support and execution, a CoS operates with a broader leadership scope – acting as an advisor, problem-solver, and operational strategist.
How to Transition from EA to Chief of Staff
Making the leap from EA to CoS doesn’t happen overnight, but by focusing on these key areas, ambitious EAs can set themselves up for success:
1. Develop Strategic Thinking and Business Acumen
- Deepen your understanding of business strategy, financials, and decision-making frameworks.
- Take an active interest in company operations beyond your executive’s immediate needs.
- Enrol in leadership courses or an MBA to enhance your strategic skill set.
2. Expand Leadership and Influence
- Begin to take ownership of high-level projects, demonstrating initiative and problem-solving capabilities.
- Cultivate relationships with key stakeholders, both internally and externally.
- Seek mentorship from senior leaders who can provide guidance and sponsorship.
3. Enhance Communication and Executive Presence
- Master the art of concise, strategic communication – both written and verbal.
- Develop confidence in presenting insights and recommendations to senior leadership.
- Position yourself as a thought partner rather than just a support function.
4. Grain Exposure to Boardroom-Level Discussions
- Request to attend leadership meetings to gain insight into strategic priorities.
- Demonstrate your ability to contribute meaningfully to discussions.
- Show initiative by anticipating business challenges and proposing solutions.
5. Refine Operational and Project Management Skills
- Strengthen your ability to oversee cross-functional initiatives and complex projects.
- Develop a structured approach to problem-solving and decision-making.
- Gain experience in budgeting, risk management, and process improvement.
What Executives Look for in a Chief of Staff
Executives who promote EAs into Chief of Staff roles often seek individuals who:
- Have a deep understanding of the business and can anticipate challenges.
- Are proactive problem-solvers who can make independent decisions.
- Exhibit exceptional leadership qualities, with strong interpersonal and influencing skills.
Executive Entourage: Your Partner in Career Progression
Not every EA is ready for the leap to Chief of Staff – but with the right development, mentorship, and opportunities, it’s a realistic and achievable goal.
At Executive Entourage, we specialise in guiding EAs through this transition, providing coaching, upskilling, and access to executive-level opportunities.
If you’re an EA looking to take your career to the next level, or an executive seeking a high-calibre Chief of Staff, let’s start the conversation. Contact Executive Entourage today to explore your next step toward executive leadership.
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