The ONE Sign You're Ready to Transition from Chief of Staff to Founder
The Chief of Staff role is all about strategy, problem-solving, and helping leaders stay focused. Maggie Olson, former Chief of Staff at T-Mobile, knows this well. Now the founder of Nova Chief of Staff, she helps others learn the skills needed for this unique position. In her chat with Emily Sander, Maggie shared practical advice and lessons from her experience.
Key Takeaways
Chief of Staff = Strategic Execution Partner
The job is not just support — it's about helping leaders stay focused on big-picture strategy while making sure the day-to-day runs smoothly.Build Around Strengths and Gaps
Maggie built a Chief of Staff team at T-Mobile by identifying gaps and hiring talent to cover areas like business planning, employee engagement, and communication.There’s a Need for Real-World COS Training
That’s why Maggie founded Nova — to help students, executive assistants, and new Chiefs of Staff gain practical skills through scenario-based assignments.
Notable Quotes
“You can’t buy more time, but a good Chief of Staff gives a leader exactly that.”
“Use each other’s templates and ideas, but make them your own.”
“Strong communication and testing new processes are key to building trust.”
Real-World Applications
Filling Organizational Gaps
Maggie built a team at T-Mobile to handle communications and employee programs.
Example: If you see a lack of structured communication in your company, propose a monthly leader newsletter.Proactively Making Recommendations
She gained trust by always coming to her leader with clear suggestions.
Example: Instead of just presenting a problem in meetings, bring 2-3 solutions and be ready to discuss.Training for Career Flexibility
Nova helps students and EAs build transferable COS skills.
Example: If you’re an EA looking to transition, take scenario-based courses to practice strategic project management.
Maggie Olson’s career shift from T-Mobile to founding Nova Chief of Staff shows how valuable this role is and how much support aspiring Chiefs of Staff need. Whether you’re a student, an EA looking to grow, or a COS already in the seat, Maggie’s advice is clear: stay adaptable, build trust through action, and never stop learning.
00:38 The Philosophy of Leadership
02:30 Maggie's Journey as Chief of Staff at T Mobile
06:39 The Structure of T Mobile and the Role of Chief of Staff
09:57 Transition from T Mobile to Nova Chief of Staff
13:24 Who is Nova Chief of Staff For?
14:50 Understanding the Role of Chief of Staff with Nova
26:59 Building Trust as a Chief of Staff
31:23 Conclusion and Contact Information
Connect with Maggie on LinkedIn
Visit Nova Chief of Staff Website
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.