How Nova Chief of Staff Trains and Educates Future Chiefs of Staff

Maggie Olson, founder & CEO of Nova Chief of Staff, brings a wealth of experience from her diverse background in retail, executive development, and leadership roles. After thriving as the first chief of staff to a Fortune 40 president, Maggie identified a significant gap in the market for chief of staff resources and training. This realization led her to establish Nova Chief of Staff, where she now helps aspiring and current chiefs of staff excel in their roles through a hands-on, practical certification course. Her journey from corporate leadership to entrepreneurship is both inspiring and impactful.

Inspiration Behind Nova Chief of Staff

SBS – What inspired you to create Nova Chief of Staff?

Maggie – After years of generalist, high-achieving environments, including Buying at Nordstrom, completing my MBA, and multi-year executive development program at T-Mobile, I didn’t hear about the chief of staff role until I interviewed for it!

I was the first chief of staff to a Fortune 40 president and built his entire chief of staff model from the ground up, including hiring a full team of seven to support his back office. I’d finally found career alignment as a chief of staff. I loved the breadth of work, the proximity to leadership, and the fact that my job was different every single day.

But when I looked for chief of staff resources, I came up empty-handed. How could there be thousands of project management certifications but nothing for chiefs of staff? It was the jumping-off point into entrepreneurship that I needed: I decided to build Nova Chief of Staff and fill this void in the industry.

Differentiating Nova’s Certification Course

SBS – How does your certification course differentiate from other leadership training programs?

Maggie – Most specifically, Nova’s Chief of Staff certification course is built for aspiring and current chiefs of staff and anyone looking to grow their career into the C-suite. I believe that confidence and competence come from hands-on practice — and that’s how I build the course.

There are dozens of hands-on assignments mirrored after real-world examples of doing the things that chiefs of staff do every single day. The course is online and self-paced, which allows students to progress through the 50–60 hours of material at their own speed. What makes it even more special is how hands-on my team is. As Nova’s instructor, each student receives multiple touchpoints with me, unlimited access to my team, and engagement opportunities with peers, too.

Essential Skills for Chiefs of Staff

SBS – What key skills do you believe are essential for a chief of staff?

Maggie – The best chiefs of staff are natural leaders, high-achieving, fast learners, driven, expert generalists, quick on their feet, okay with being behind the scenes, have excellent emotional intelligence, strong project managers, and can work at both a 10k foot view, and deeply in the weeds if needed.

Leadership Lessons from Nordstrom

SBS – How did your experience at Nordstrom shape your approach to leadership?

Maggie – I learned so much about leadership during my time at Nordstrom. Looking back, as a buyer in five different buying offices over five years, I liken my experience to that of a consultant. I learned how to walk into a new business with completely new people, processes, and products and very quickly learn and improve that business. I had to learn how to observe first and act second, how to gain followership even without direct reports when I was earlier in my career, and how to implement change with buy-in from the team. It wasn’t always smooth, but I had many incredible leaders to learn from, who both believed in me and gave me important feedback on my approach. The leadership growth I had during my time at Nordstrom was unparalleled.

Transitioning from Retail to Tech

SBS – What motivated you to transition from retail to technology sectors?

Maggie – I went back to school in the evening (while Buying at Nordstrom) to get my MBA. Folks like to say that you get an MBA to either “move up, start up, or change up.”

I wasn’t planning on changing it up, but during my second year, I was contacted by T-Mobile recruiters about their Leaders 2 Executive Program. This was a highly competitive post-MBA rotational program for which about five students across the country were selected based on past leadership and future potential. The program provided incredible access to company executives and invested deeply in us as future leaders, and I loved what T-Mobile stood for. Very similar to Nordstrom, T-Mobile puts their customers and their employees at the center of everything they do — and I saw this firsthand from their executives. An incredible company culture is built off of these principles, and this is how I strive to run Nova as well.

Identifying Market Gaps in Chief of Staff Training

SBS – How did you identify the gap in the market for Chief of Staff training and education?

Maggie – As the B2B President’s chief of staff, after building out the full back office team of seven, designing everyone’s roles, responsibilities, and processes, and then teaching everyone on my team what needed to be done, I felt like I’d just received an MBA in chief of staff training! When I realized that an online certification course for chiefs of staff didn’t exist in the market, it was a no-brainer: I deeply loved the work, I loved teaching and leading others, and I was ready for entrepreneurship. After a year of building the course, moving across the country, and being pregnant and then with an infant, Nova’s Chief of Staff Certification course was built.

Common Misconceptions About Chiefs of Staff

SBS – What are the most common misconceptions about the role of a Chief of Staff?

Maggie – The chief of staff role is not well understood. The title indicates having “staff” when it’s actually less common to have direct reports as a CoS. Additionally, many confuse chief of staff and executive assistant (EA), but the distinction is important: chief of staff is a high-level, strategic thought partner to the business leader. They exist to drive alignment across the leader’s team, manage and own key priorities for the executive, and maximize the business leader’s time. An EA will always have core admin functions that a chief of staff rarely holds, including calendar & inbox management, expensing, travel coordination, and general logistics.

Leadership Style Influences from T-Mobile

SBS – How has your time at T-Mobile influenced your leadership style?

Maggie – The Leaders 2 Executive program at T-Mobile was pretty hardcore, and I loved it. In my first rotation, I was sent to a city I’d never been to lead 100 store employees across 10 stores in an industry (telecom) that I’d never worked in. I was tasked to improve business, gain followership, and make a big impact across the whole market (100+ stores). Thankfully, I loved my time in Salt Lake City as district manager for those T-Mobile stores, and I learned so much about operations, presenting business to leadership, and leading people in unfamiliar environments.

For my second rotation, I was part of the retail strategy team and worked on new store concepts. I had incredible leaders in both roles who taught me about leader information flow and using humor and vulnerability to relate to people. In the second role, I refined my storytelling & presentation skills further and then dove deep into cross-functional project management as I led the COVID response retail stores. It was incredible working so close to senior leadership throughout the rotational program and as chief of staff. The lessons learned from executives about what to spend your time on and how to get what you need when you need it was unparalleled.

Advice for Aspiring Chiefs of Staff

SBS – What advice would you give someone aspiring to become a chief of staff?

Maggie – First, talk to the chiefs of staff! Ask them questions about the role so you can clearly understand what they do and what you’re getting into. Second, check out Nova Chief of Staff. We’re market-leading for a reason. We care deeply about our student experience, and we’re proud to share that our students leave us excited and confident to take on the chief of staff role.

Ensuring Course Relevance and Applicability

SBS – How do you ensure the relevance and applicability of your certification course content?

Maggie – Our course is organically endorsed by over a dozen thought leaders in the industry who reviewed the content before endorsing it. We have also partnered with a handful of experts who’ve reviewed the course and created additional optional content that students have requested. We also stay very close to what’s happening in real-time in the market. Nova constantly consults with businesses and leaders about their needs and coaches many aspiring and existing chiefs of staff on the role, helping us ultimately stay connected to what’s freshest and most relevant in the CoS space.

Success Story: From Student to Chief of Staff

SBS – Can you share a success story of a student who benefited from your certification course?

Maggie – One of our students, Nicola, a rockstar senior executive assistant, completed our course recently. She shared with us that the course was “life-changing.” Her confidence and self-belief skyrocketed, prompting her to apply for the chief of staff role she’d been eying — and she got it! She’s incredible, and we’re so glad the course has helped her see this and prepared her for the position.

Strategies for Building an Efficient Executive Team

SBS – What strategies do you recommend for fostering a supportive and efficient executive team?

Maggie – To foster a supportive and efficient team, the team must have access to the leader and transparency into their priorities. This is usually accomplished through excellent organization and communication. A strong rhythm of business should allow for adequate access to move the business along efficiently, and a solid process around sharing priorities will help with executive team alignment. At the end of the day, an executive team is just like any other team. To be successful, they need time with their leader, the ability to get approvals to move their business along, feeling cared about and prioritized, and feeling in the know about what’s most important for the team.