From EA to Chief of Staff: Mastering Multitasking Overseeing Nine Different Companies
Going from an Executive Assistant (EA) to Chief of Staff is no small leap. It takes focus, adaptability, and a whole lot of multitasking. But what does that transition really look like? In this blog, we hear firsthand from Brandy Willis, who’s done it—managing not just one but nine companies at the same time.
Key Takeaways
Become invaluable through business knowledge: By thoroughly understanding the business operations, Brandy knows details her principal sometimes forgets—becoming an indispensable resource.
Effective time management requires prioritization: With nine companies to support, Brandy focuses primarily on the "big four" companies housed at their corporate office, while remaining flexible to address needs across all businesses.
Objectivity matters in family businesses: Working with both her principal and his wife (who owns another company), Brandy maintains objectivity when navigating family dynamics and business decisions.
Notable Quotes
"It's being proactive... I'll just do it right when he says it instead of waiting for a task list."
"Make yourself invaluable... make sure you know the business inside and out.
"Being more objective and not letting your personal feelings or your personal thoughts get in the way of your success."
Real-World Applications
Active listening as information gathering. Brandy listens to her principal's calls and conversations, even while working on other tasks. When he mentions delegating something to her, she often completes it immediately—eliminating the need for follow-up and reducing their collective task list.
Communication tailoring for effectiveness. Understanding her principal doesn't regularly check email, Brandy screenshots important information and texts it to him instead. This simple adaptation significantly improves their communication flow and ensures critical information reaches him.
Navigating family business dynamics. When handling matters involving both her principal and his wife (who has her own business), Brandy maintains appropriate boundaries and serves as a neutral facilitator—addressing issues directly with each party as needed.
The jump from EA to Chief of Staff isn’t about doing more—it’s about doing things differently. It’s about strategy, smart decisions, and knowing where to focus. If you’re aiming for that role, start implementing these habits today.
About The Author
Emily Sander is an ICF-certified leadership coach with more than 15 years of experience in the business world and the author of Hacking Executive Leadership. She’s been featured in several print publications, online articles, and podcasts, including CEO Today Magazine, Leading to Fulfillment, and Leadership Powered by Common Sense.
Emily has a passion for helping business leaders reach their full potential. Go here to read her story from seasoned executive to knowledgeable coach. If you want to send Emily a quick message, then visit her contact page here.