Exploring the Chief of Staff Role, Embracing Failure, and Building Confidence with Maggie Olson

Hallie speaks with Maggie Olson, creator of the first-of-its-kind Chief of Staff Certification. Maggie shares her journey to Chief of Staff, highlighting the importance of every experience as a stepping stone towards success. We delve into the pressures of societal norms, mental health, and gender disparities in risk-taking and explores the nuances of the Chief of Staff role, explaining whether an MBA is necessary for a Chief of Staff role, the importance of setting boundaries, and negotiating better pay. Tune in to learn what it truly means to be a Chief of Staff and how you can grow even further with the Chief of Staff Certification!

BONUS: Maggie is extending a special offer to The Founder & The Force Multiplier community. Anyone who finds out about the Chief of Staff Certification through us will receive a FREE 30-minute coaching session after completing the course. Thank you, Maggie!


References & More

Maggie Olson Consulting

Chief of Staff Certification

Follow Maggie on LinkedIn

The Confidence Code by Katty Kay and Claire Shipman



[0:00] Maggie shares her journey to Chief of Staff and shares how her breadth of experience, passion, and drive to learn, understand, and make processes more efficient has been crucial for her success in the chief of staff role.

[06:25] Maggie sheds light on the concept of a “generalist leader”, taking us through her own evolution, how she gained confidence, the lessons embedded in failures, and the importance of risk-taking,

[8:08] We explore how our upbringing and societal constraints can influence our fear of failure and risk-taking. 

[12:56] We talk about how the language used in job descriptions can have an impact on who applies and the confidence required to do so.

[15:06] Maggie highlights the indispensable nature of understanding a company’s DNA – its culture, processes, and team dynamics.

[21:16] The path to Chief of Staff is a one with diverse routes. We explore instances when acquiring an MBA becomes crucial, and the art of persuading a CEO about the need for a Chief of Staff.

[27:45] One of the most nuanced aspects of stepping into a CoS role is establishing rapport with an EA, especially one seasoned in their position. Maggie offers a treasure trove of insights on building this relationship grounded in mutual respect, humility, and an openness to learn.

[29:21] We also talk about the importance of getting buy-in from your EA, and how to do so in a way that fosters trust and cooperation.

[31:50] Maggie presents her Chief of Staff Certification Course, tailor-made for generalist leaders. The course, as she details, is meticulously structured, promising definitive learning outcomes and arming participants with a unique skillset to thrive in Chief of Staff roles.

[40:30] Maggie shares her coaching offerings and provides a generous offer of 30 minutes of coaching to anyone who takes her certification.

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