We caught up with the brilliant and insightful Maggie Olson a few weeks ago and have shared our conversation below.

Maggie, thanks for taking the time to share your stories with us today So, let’s start with trends – what are some of the largest or more impactful trends you are seeing in the industry?

My first Chief of Staff role was in 2020. I felt alone on an island with no support, no resources, and no community. Thankfully I knew two other Chiefs of Staff in my company that helped me with a template or two, but without them, I would have been completely on my own. That’s not the case anymore.

Business owners, CEOs, and Founders are telling their friends about the power of a Chief of Staff. Kickass Senior Executive Assistants are breaking through the glass ceiling and getting promoted. Chief of Staff Membership communities have been built, and learning resources, like Nova, are hitting the market.

As an undergrad economics major, I speak in “supply and demand” terms. And it’s clear in this situation: demand is driving supply. The market is demanding Chiefs of Staff, the role is increasing in popularity and more people are moving into Chief of Staff roles than ever before. It’s a huge trend and it’s here to stay. I fundamentally believe that we will look back at the Chief of Staff role as one of the most impactful positions of our generation.

Why? Because leaders have long known they need high-level, administrative support. They’re now catching on to the fact that they also need high-level, strategic, execution-focused support to help them manage, prioritize, and accomplish their most important initiatives that have nowhere else to land. And if you’ve ever been around a visionary leader… you know they have a lot of them!

The issue I’m up against is awareness and understanding of the role. It’s often confused with executive assistant (two very different roles working closely together) and the title leaves a lot to the imagination (in fact, many Chiefs of Staff do not have any direct reports). But usually, once I help business leaders understand the role, they want one yesterday.

To illustrate, I was at a CEO training recently in Austin, TX with 13 Founders. Only 1-2 had previously worked with a Chief of Staff or understood the role at all. By the end of the training all 13 were in on Chief of Staff! They saw the value and had so many questions about exactly how a CoS could help them (usually it just comes down to funding the role). When I returned home, one of the Founders put me in touch with 8 other Austin Tech Founders, all interested in the Chief of Staff role. There’s not much convincing necessary: Chief of Staff is a clear need for every business leader.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

After a career in people leadership and customer experience at companies including Nordstrom, Starbucks, and T-Mobile, I found myself in a Chief of Staff role to the President of the B2B organization at T-Mobile. He’d never had a Chief of Staff before, I’d never been one, and on top of that, I’d never heard of the role before interviewing for it.

All I understood during those Chief of Staff interviews was that I was being brought on to support his back office, drive alignment & organization across his leadership team, ensure he was more prepared than he’s ever been, and elevate everything around him through process, problem-solving, transparency, and communication. Are you kidding me? My eyes were wide with excitement…this role was made for me.

I always enjoyed work, and even more so, I enjoyed being successful at work: moving from role to role, promotion to promotion, being reliable, accountable, and looked to as a leader. But I’d never felt that “perfect fit” in my career – until I found Chief of Staff.

As his first Chief of Staff, I was privileged to have full support in building his back-office team. After 11 months, I’d built a team of seven who all supported different Chief of Staff functions: from business planning, president engagements, employee culture, events & communications, and various program & project management support. I designed each hire’s role, responsibility, process, templates, and more. After 18 months in the role, we were a well-oiled machine, and I was ready for my next challenge.

Since completing my MBA (Go Huskies!), I’d had a newfound appreciation & understanding of the world of entrepreneurship – I was ready to get out there on my own. I figured fractional Chief of Staff consulting was the perfect next step. I built my website and my offer… but something was missing. I had just moved mountains with what I’d built… how could I use this knowledge, insight, and expertise?

I remember it vividly, I was sitting on the couch in my mom’s house in New Mexico telling her how crazy it is that there are thousands of project management certifications out there, but nothing for Chiefs of Staff to get hands-on self-paced experience online doing the things that Chiefs of Staff do every day. And she said, “Well, why don’t you build it?”

So here we are (thanks, Mom!). Nova’s Chief of Staff certification course launched last summer, and it’s been incredibly well-received in the market. With over 500 students across 22 countries, the feedback is staggering: graduates are walking away with confidence and validation that they can do the role of Chief of Staff and the resources to hit the ground running.

The course is self-paced and online, offering 50 hours of content, multiple touchpoints with me, optional touchpoints with peers, optional assignments based on student requests, guest instructors, lifetime access, and so much more jam-packed in there. It’s Nova’s premier product reaching both B2B and B2C customers, but we also offer coaching, consulting, and recruiting/placement at Nova.

For the first time, this Fall we will be teaching Nova’s course in-person! We’re thrilled for the partnership with APC, a major conference & event company, which we’re working with for several more in-person Nova course trainings throughout next year.

I credit a lot of my success as a new entrepreneur to my experience as a Chief of Staff. From breadth to strategy to prioritization… there truly is no better way to learn how to run a company than from leaders at the top of a business.

Any insights you can share with us about how you built up your social media presence?

I’ve had a career that I term “expert generalist” – I’ve dabbled in just about everything… except brand-building & marketing! But I believe the sign of a great leader is knowing what you’re not good at and when to call in support, and that’s what I did. I hired an incredible marketing agency to help build the Nova Chief of Staff brand, and I took the advice of some trusted peers who told me to start posting every single day on LinkedIn.

In less than 11 months, I’ve grown my personal LinkedIn following from very few to over 17k. I ask for help, I speak to every single leader I can in the industry, I share resources & tips, and I test & learn constantly.

With a career in customer experience, I am practiced in putting myself in “the customers” point of view. What do they want to hear about or share? What do they care about the most? How can I help those following me? John Ledger, former T-Mobile CEO, is famous for saying, “shut the F*** up and listen to your customers.” And Nordstrom’s values are built on this concept as well. I’d like to say I was raised with this perspective from early in my career.

How’d you build such a strong reputation within your market?

I ask myself this a lot. Nova was welcomed with open arms in this market right away, and although the brand hasn’t quite been around for a year yet (we branded as Nova after our course launched) it feels like it’s years old. How have we done this? Looking back, it was not an intentional business development strategy, but more so an “I don’t quite know what I’m doing so I’m going to build relationships… strategy.” And it worked.

But first, I’d be remiss not to mention that what’s helped the most to build our strong reputation in the market is – above all else – an excellent product with great reviews, testimonials, and case studies. Without that, there’s nothing to build on and no reputation to withstand.

But through intentional relationship-building with those in the industry, meaningful and deliberate partnerships formed very quickly. In the early days of launching our course last year, I reached out to every single person who was a business leader or thought leader in the space. I got to know them, built trust, and learned from them. Over time, I’ve built an event strategy to help my partners gain exposure, and I’ve joined numerous podcasts and webinars to help their audience learn about us. As a core priority of ours, I continue to nurture all our partnerships and build new ones thoughtfully and creatively.

Contact Info:

• Website: https://www.novachiefofstaff.com/
• Instagram: https://www.instagram.com/novachiefofstaff/
• Facebook: https://www.facebook.com/NovaChiefofStaff/
• Linkedin: https://www.linkedin.com/in/maggie-olson-cos/
• Twitter: https://x.com/NovaChiefofStaf
• Youtube: https://www.youtube.com/@novachiefofstaff
• Other: https://www.tiktok.com/@novachiefofstaff
  https://www.instagram.com/maggiej_5/?hl=en
  https://www.linkedin.com/company/novachiefofstaff

Image Credits

Nikki Moore Photography