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Mastering the Chief of Staff role with Maggie Olson

Executive Office Insights

Release Date: 08/28/2024

Upskilling and community building in Ghana (Audio only) show art Upskilling and community building in Ghana (Audio only)

Executive Office Insights

208: In this episode, I sit down with Rebecca Afful to explore how the Executive Assistant profession is evolving. We discuss how Executive Assistants can take ownership of their careers, develop a powerful mindset, and build the skills needed to thrive in the future of work. In this episode, you'll discover: - How professional communities accelerate career growth - Why mindset is the foundation of a successful Executive Assistant career - How AI is reshaping the administrative profession - How the Global Skills Matrix supports long-term career development - The importance of networking,...

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Executive Office Insights

207: What does it take to move beyond managing calendars and become a trusted business partner? In this episode, we explore the future of the Executive Assistant profession and the mindset shift required to create strategic impact. Debbie shares powerful lessons on executive presence, communication, leadership, and why soft skills remain essential in the age of AI. From building trust with leaders to using data to drive better decisions, this conversation offers practical insights for Executive Assistants, Administrative Professionals, and Chiefs of Staff who want to think beyond tasks and...

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Executive Office Insights

206: Wird KI die Assistenz ersetzen, oder ihre Rolle sogar stärken? In dieser Podcast-Folge sprechen wir über die praktische Nutzung von Microsoft Copilot, den Einsatz von KI im Arbeitsalltag und die Veränderungen, die aktuell in Unternehmen stattfinden. Warum haben manche Organisationen KI bereits fest in ihrer Arbeitsweise verankert, während andere noch ganz am Anfang stehen? Welche Aufgaben lassen sich heute schon automatisieren – und wo bleibt der Mensch unverzichtbar? Außerdem geht es um typische Anwendungsfälle für Assistenzen, den Umgang mit Datenschutz, die Bedeutung von...

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Executive Office Insights

205: What does a Chief of Staff actually do — and why are more CEOs hiring them than ever before? In this episode, Clara Ma breaks down the real role of a Chief of Staff inside fast-growing startups and modern leadership teams. From executive strategy and hiring to AI, remote work, and scaling companies, this conversation explores why the Chief of Staff role is evolving so quickly. We talk about: - Chief of Staff vs Executive Assistant - How CEOs hire the right strategic partner - Startup leadership and operations - AI tools and AI literacy for Chiefs of Staff - Emotional intelligence in...

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Executive Office Insights

204: Eine internationale Geschäftsreise. Ein gesperrter Luftraum. Und plötzlich werden aus wenigen Stunden ganze elf Tage im Ausnahmezustand. In dieser Podcastfolge erzählt Tanja Donislreiter von einer Reise, die völlig anders endete als geplant: Nach einem Meeting in Indien strandet sie gemeinsam mit einem Kollegen in Doha – mitten in einer geopolitischen Krisensituation. Was folgt, sind Tage voller Unsicherheit, Alarmmeldungen, spontaner Entscheidungen und emotionaler Momente. Wir sprechen über: - Krisenmanagement unter extremen Bedingungen - mentale Stärke und Resilienz -...

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Executive Office Insights

203: Was passiert, wenn man eine erfolgreiche Konzernkarriere hinter sich lässt – und komplett neu anfängt? In dieser Folge spricht Annika Tringali über ihren Weg in die Selbstständigkeit als virtuelle Executive Assistant und die Entscheidungen, die sie dorthin geführt haben. Du erfährst, wie sich Arbeiten im internationalen Umfeld wirklich anfühlt, welche Herausforderungen hinter einem scheinbar klaren Karriereweg stecken und warum ein Neustart oft weniger geplant ist, als man denkt. Es geht um echte Einblicke in den Arbeitsalltag auf Top-Management-Level, um persönliche Wendepunkte...

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Executive Office Insights

202: She built a global business for assistants, starting with a simple blog. In this episode, Nicky Christmas shares how she went from Executive Assistant to founder of The EA Campus and what it really takes to turn a side project into an international platform. Instead of following a traditional career path, Nicky created something that didn’t exist at the time: a space for assistants to learn, grow, and be taken seriously. Today, her platform reaches thousands of Executive Assistants and Personal Assistants globally through online courses, virtual summits, and a strong professional...

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Executive Office Insights

201: In this episode, we break down why decisions inside companies often stall, even when everyone seems aligned. Tina Ramamurthy shares her experience from working inside a CEO Office and explains what happens between strategy and execution as companies grow. Tina Ramamurthy has built a career in the space between decisions and execution, where good intentions drift and effort quietly replaces strategy. She focuses on what happens as complexity increases and systems start to bend. At Babbel, she built and led the CEO Office as the company scaled from €100m to €300m on the path to IPO...

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Executive Office Insights

200: What is it really like to work at the highest levels of American politics? In this episode of the Executive Office Insights Podcast, Opal Vadhan shares her extraordinary journey from an intern in the Obama White House to becoming the personal aide to Vice President Kamala Harris. As a first-generation Indian American raised in Queens, New York, Opal offers a powerful perspective on leadership, public service, and the importance of empathy in high-pressure environments. She reflects on her years working closely with Secretary Hillary Rodham Clinton before joining the...

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Executive Office Insights

199: Moderne Assistenz, smarte Tools und Microlearning, so sieht erfolgreiche Zusammenarbeit 2026 aus! In dieser Podcastfolge sprechen Florian Sandmann-Reetz und Dorothea Steinmetz über moderne Führung, Assistenz auf Augenhöhe und den strategischen Einsatz von Microsoft 365, Copilot und dem neuen Outlook. Du erfährst: - Warum Vertrauen wichtiger ist als Mikromanagement - Wie Aufgabenmanagement mit Outlook, Planner & To Do wirklich funktioniert - Warum das neue Outlook besser ist als sein Ruf - Wie Copilot und KI den Arbeitsalltag verändern - Weshalb Microlearning die Zukunft der...

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144: With extensive experience at some of the biggest companies in retail, food & beverage, and technology, Maggie has stepped into new roles, new industries, and new businesses and transformed teams and businesses from the ground up over and over again.

In her most recent corporate role working as Chief of Staff leader to a President at a Fortune 40 company — a multibillion-dollar business with 5,000+ employees — Maggie built the president’s Chief of Staff model from the ground up. In doing so, she created a highly successful team, drove major organizational efficiencies, and implemented executive back-office processes and structure that will be in place for years to come.

Maggie has 20 years’ experience leading large teams and has spent her career focused on both the customer and employee experience. Working for Nordstrom early in her career solidified her passion for customer experience, where she spent 6 years, first as a Buyer working in 5 different buying offices, and then with the Technology team, honing Business Process and Project Management skills building user tools.

While working at Nordstrom, Maggie went to graduate school in 2015. During the MBA program at the University of Washington’s Foster Business School, she was recruited for an ultra-competitive Executive Development Program with T-Mobile. Here she led a district of stores to success in an industry she’d never worked in and a city that was new to her, presenting her business to company leaders every month. She then moved into a Retail Strategy role working on Human Strategy for new store concepts, building on her digital presentation and storytelling skills. When COVID hit and retail was shuttered, Maggie led the COVID Response initiative for the retail organization, mobilizing 26k retail employees to work in the back of closed stores through Virtual and Telesales pilot programs. From here, she moved into the Chief of Staff position for the President of the B2B organization.

As the owner of Nova Chief of Staff, Maggie leads the Chief of Staff Certification course and coaches Chiefs of Staff. She is also a fractional Chief of Staff consultant, focused on helping mission-driven, for-profit startup founders scale their businesses quickly. In her spare time, Maggie loves spending time outside with her husband, their animals, and their 1-year-old, Max!

Links:

 🔴 Watch the Episode on YouTube: https://youtu.be/eeBrtoZNYOY

http://www.novachiefofstaff.com

http://www.novachiefofstaff.com/syllabus

http://www.novachiefofstaff.com/shop (AI course will be here)

www.linkedin.com/in/maggie-olson-cos


Diana’s CoS training: https://www.haufe-akademie.de/35353

Diana’s CoS certification: https://www.haufe-akademie.de/36524

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

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

 

Podcast on YouTube: https://www.youtube.com/@the-socialista-projects

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

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