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Working with Michelle Obama: A chat with Chynna Clayton [Summer Edition]

Executive Office Insights

Release Date: 07/16/2025

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Executive Office Insights

191: What if the key to growth isn’t working harder — but working together? In this inspiring long-form conversation, Working Out Loud founder John Stepper reveals how peer-to-peer development, shared learning, and authentic human connection can transform not only careers but entire organizational cultures. John shares the origin story of Working Out Loud (WOL), now used in more than 100 global organizations, and explains why meaningful relationships, psychological safety, and generosity are at the heart of effective personal development. We explore how WOL circles spark confidence,...

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Executive Office Insights

190: What does Formula One teach us about being an exceptional executive assistant and strategic partner at the top level? In this inspiring episode, Nicole Bearne shares her journey from supporting one of Formula One’s most respected leaders to becoming a communications expert and business founder. She takes us behind the paddock doors to reveal what it’s really like to work alongside Ross Brawn, Michael Schumacher, and Lewis Hamilton—where every second counts and preparation is everything. You’ll discover how executive support plays a crucial role in leadership success, team...

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Executive Office Insights

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Executive Office Insights

188: What if your biggest distraction could become your greatest productivity superpower? 💡 In this inspiring and practical talk, Lauren Bradley, founder of The Officials, reveals how AI, tech, and ADHD can combine to help executive assistants, office managers, and admin professionals not just survive—but thrive in today’s fast-changing digital world. Discover how to harness AI tools like Notion, Microsoft Lists, and Power Automate, create smart workflows, and build confidence through automation, mentorship, and community. Lauren also opens up about living and...

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Executive Office Insights

187: What does it really take to be Chief of Staff at Harvard Business Publishing? I sit down with Concetta Green, Chief of Staff at Harvard Business Publishing, for an inspiring deep dive into leadership, career growth, and purpose-driven success. From her journey as an assistant to becoming a trusted executive partner, Concetta reveals why purpose matters more than titles, how mentorship and kindness shape real leadership, and why administrators are the unseen backbone of business. She also shares how faith and grace help her navigate challenges and create...

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Executive Office Insights

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185: Go behind the scenes of Microsoft Germany’s CEO Office with two inspiring women: Andrea (Executive Assistant) and Svetlana (Chief of Staff). In this candid conversation, they share what it really takes to support a top executive, manage complex schedules, and keep leadership moving at full speed. Discover: ✅ The difference between an Executive Assistant and a Chief of Staff ✅ How to manage the CEO Office of Microsoft Germany ✅ Career insights and skills for assistants and chiefs of staff ✅ Tools and strategies that keep leadership effective ✅ Why collaboration and trust are...

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Executive Office Insights

184: Wie schafft man es, mit Ende 50 noch einmal beruflich neu durchzustarten? In dieser Folge erfährst du, wie Cornelia Bahr den Mut gefunden hat, einen kompletten Jobwechsel anzugehen – und welche Strategien, Netzwerke und Weiterbildungen ihr geholfen haben. ✨ Du bekommst praxisnahe Tipps für berufliche Veränderung im Alter, erfährst, wie man den eigenen Marktwert erkennt, neue Chancen nutzt und auch in einem völlig neuen Umfeld schnell ankommt. Diese Episode ist vollgepackt mit Motivation, echten Karriere-Erfahrungen und klaren Schritten für alle, die sagen: „Es ist nie zu...

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Executive Office Insights

183/124: Samantha Cox's career journey is indeed impressive and diverse, showcasing her expertise in Executive Assistant, Hospitality, and VIP Guest Services roles. Her extensive experience, spanning over 20 years, has involved working with high-profile clients and in various locations around the world. One notable highlight is her time working for Sir Richard Branson, the Founder of the Virgin Group. During her tenure, she not only served as an executive assistant but also became part of a select group managing personal affairs, budgets, charitable initiatives, and coordinating celebrity...

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Executive Office Insights

182/149: Entdecke, wie Diversität und „New Work“ die Arbeitswelt verändern und was moderne Unternehmen tun, um ein inklusives Arbeitsumfeld zu schaffen! Begleite mich in diesem aufschlussreichen Gespräch mit Dominique Jäger, in dem wir über die Bedeutung von Diversität und Inklusion im heutigen Arbeitsumfeld sprechen, die Zukunft der Führung beleuchten und wie flexible Arbeitsmodelle unseren Ansatz zur Produktivität und Work-Life-Balance verändern. Dominique teilt ihren Weg von ihren ersten Rollen in der Beratung bis hin zur Führung von Diversity-Initiativen bei der DKB und gibt...

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177/143: Empathetic, strategic, and meticulous about the details, Chynna Clayton has built a career enabling some of the world’s most influential leaders to excel in high stress environments.

Chynna is the founder and CEO of Matriarch Made Development, a consulting firm that centers around helping companies and organizations develop high performing administrative teams, identify and address overall operating structure and event logistics inefficiencies and further cultivate assistant’s talents.

Named in honor of the four generations of maternal women who have paved the way for her to mature into the woman she has become today, Matriarch Made was founded on the principles that enabled Chynna to build a distinguished career in personal, government, and corporate environments.

Raised by a single mother in Miami, Florida, on the outskirts of Liberty City. Chynna studied Event Management and Political Science with a minor in Business at the University of Florida. A proud Florida gator, Chynna’s time at UF helped her to gain exposure to event management as a White House intern during the Obama administration. Upon graduation, Chynna spent years supporting the Obama’s advance logistical teams until leaving her administrative role at The Walt Disney Company to ultimately become the “body-woman” of former First Lady Michelle Obama. In this capacity, Chynna helped Mrs. Obama connect with communities around the world. She ensured every detail of Mrs. Obama’s personal and public facing events were executed flawlessly, directing teams who coordinated Mrs. Obama’s domestic and international engagements.

At the conclusion of the Obama administration, Chynna was retained by the personal office of Barack and Michelle Obama as their Director of Travel and Event Operations, where she continued to help manage the personal obligations of their family while continuing to oversee the coordination of Mrs. Obama’s engagements.

Now at Matriarch Made Development, Chynna helps leaders build core competencies such as but not limited to organization, teamwork, communication, problem solving, accountability and composure in administrative and executive teams. From executive training and coaching to equipping organizations with tools such as scheduling systems, templates, tactics, processes/procedures, events logistics guidance; Matriarch Made helps leading organizations build a systems approach to tackling the inefficiencies that stifle overall potential.

Chynna was most recently highlighted in Michelle Obama’s newly released book, “The Light We Carry.” She has written for O Magazine; been featured in Essence, the Miami Herald, the University of Florida Health and Human Performance Magazine, the Netflix Documentary “Becoming,” and the Michelle Obama Spotify Podcast. Chynna strives every day to be an inspiration for young girls, especially those who have experienced similar life challenges. Chynna resides in Washington, DC with her wife Katina Hoyles.

Links:

🔴 Episode on YouTube: https://youtu.be/2FWphgr6AbA 

Chynna's Website: https://www.chynnaclayton.com/
Chynna on LinkedIn: https://www.linkedin.com/in/chynna-clayton-248b145b/

Diana on LinkedIn: https://www.linkedin.com/in/diana-brandl/

The Future Assistant Newsletter: https://the-socialista-projects.com/#newsletter

Podcast on Spotify: https://open.spotify.com/show/3qBSDjTfYOG2x6qos7dKkS

Podcast on Apple Podcast: https://podcasts.apple.com/de/podcast/the-future-assistant/id1493106661