285: Why Every Visionary CEO Needs a Chief of Staff ft. Maggie Olson

Feeling overwhelmed trying to do it all? Wondering if it’s finally time to hire a right-hand leader to help scale your business? This episode will show you what it really takes to let go and grow.

On this episode of The Root of All Success, Jason Duncan welcomes Maggie Olson, founder of Nova Chief of Staff, to unpack the misunderstood and often underestimated role of a Chief of Staff. From leading internal transformation at T-Mobile to building the world’s first Chief of Staff certification program, Maggie shares her personal story and expert insight on how business leaders can stop spinning their wheels and start leading with purpose.

🔑 Takeaways from this episode:

• How to know when it’s time to hire a Chief of Staff
• The critical difference between an EA and a Chief of Staff
• What visionary CEOs get wrong when hiring
• The true cost (and ROI) of hiring a Chief of Staff
• What to expect from Nova’s training and placement programs
• How to stop "idea whiplash" and bring alignment to your team
• Why strong leadership isn’t about control—it’s about clarity

Whether you’re a startup founder, a growing CEO, or a solo entrepreneur who feels buried in execution, this conversation is packed with real-world advice to help you reclaim your time and refocus on what matters most.

Who is Maggie Olson?

Maggie Olson is the Founder of Nova Chief of Staff, the premier and first-of-its-kind destination for Chief of Staff education, certification, and development. She has 20 years of experience in retail, food and beverage, and technology sectors and has held leadership roles at Nordstrom and T-Mobile. At T-Mobile, Maggie's impressive work led her to become the first Chief of Staff to the President of the T-Mobile Business Group. In this role, she built the Chief of Staff model from the ground up, creating a highly efficient team and establishing an executive back-office structure, supporting the President, SVPs, and over 5,000 employees. She also built a Chief of Staff team, defining all roles, processes, and systems. Through Nova Chief of Staff, Maggie continues to shape the future of business leadership, providing the tools and resources necessary for Chiefs of Staff to excel in their roles and drive company success.

Maggie’s Website Link: https://www.novachiefofstaff.com/

Maggie’s Social Media Link:

https://www.linkedin.com/company/novachiefofstaff

https://www.instagram.com/novachiefofstaff/

https://www.facebook.com/NovaChiefofStaff/

https://www.tiktok.com/@novachiefofstaff

https://www.youtube.com/@novachiefofstaff

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