The Ultimate Guide to Understanding the Chief of Staff Role

Earlier this year, I attended a CEO retreat in Austin, TX, with a dozen tech startup founders. Being a Seattle native and a new mom, as I drove through the massive tree-lined property and walked into the ranch-style mansion of a guesthouse, it’s safe to say that I was in for an adventure. Although I was there to learn, I’d also been asked to attend by the training’s founder; he was interested in a potential partnership with me relating to the Chief of Staff training company I'd recently built (Nova Chief of Staff).

What I walked away from the retreat with was a whole lot more than the usual education, friends, and motivation from an experience like this. I left with a renewed FIRE for my role as Nova’s Founder and a whole new purpose: to spread awareness and education about the power of a Chief of Staff to as many business leaders as possible.  

Ten out of twelve of the founders I spent three days with had never heard of the Chief of Staff role. But after our first night at dinner, where I spent a few minutes introducing myself, describing the role, and then sharing exactly how a Chief of Staff could help each one of them free up their time to focus on the future, vision, strategy, and growth of their companies... every single founder was nodding their head saying, “I need a Chief of Staff.”

And I'm here to tell each of you that, yes, you do.

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What is a Chief of Staff?

 A Chief of Staff is a business leader’s right-hand and strategic thought-partner focused on executing, organizing, and prioritizing the leader’s business initiatives, and driving transparency and alignment across the leadership team. A CoS exists to maximize the leader’s time and exponentially increase their impact.

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How is a Chief of Staff different from an Executive Assistant?

While an Executive Assistant (EA) may fill gaps or lead certain projects, a Chief of Staff is a higher-level leader who’s capable of leading strategic, cross-functional projects and carrying out their execution. Additionally, a CoS rarely holds the core responsibilities of an EA: calendar, inbox, travel, expenses, and logistics.

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What can I expect from a Chief of Staff?

• Establishes and leads the rhythm of business
• Oversees the leader’s back office
• Executive project management
• Involvement in communications and events
• Strategic recommendations to improve the business
• Identifies process improvements to drive efficiency
• Major problem solver, removing roadblocks for others
• Ensures the leader is prepared for everything they walk into
• Fills strategic gaps in the business
• Leads key business initiatives
• Leads cross-functional teams and projects

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With a more senior Chief of Staff, you should also expect:

• Leading higher-level projects like board and investor relations
• Acting as an advisor and proxy to the business leader
• Owning major business or company initiatives

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What should a Chief of Staff focus on first?

The biggest mistake that leaders and Chiefs of Staff make is pointing the CoS to company problems too soon. Here is what the CoS should be focused on in the first 2-3 months:

1. ‍Relationships: with the leader, the leader’s executive team, the EA, and any other key player on the team. 1:1s should be reoccurring regularly between these parties with the goals of building trust and establishing business understanding of the day-to-day and key priorities across the team.
2. ‍Back Office Ops: before tackling company initiatives the leader’s back office must be operating well. Usually, this means the CoS should be working to establish systems, processes, and tools to support the business leader before anything else.
3. ‍Financial Acumen: Some of the best Chiefs of Staff may come from a completely different industry, bringing their diverse experience to you and your company. For this reason, it’s important for a CoS to dive into learning the most important metrics that drive your business quickly. Identifying a financial resource goes a long way here: a CoS should have an overview session with someone on the financial team and then revisit with them to dive deeper as needed.

In a world where you can buy everything except for time, a Chief of Staff is the closest thing a business leader can get to buying time. If you’ve been considering how a CoS can help you, I always suggest hiring administrative support first (EA) to ensure the high-value role of CoS steers clear of any administrative duties. And if you have a rockstar executive assistant who’s hungry, curious, and leads some major strategic projects for you? Consider promoting them to Chief of Staff. We’d be happy to help train them!

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About the Author, Maggie Olson, Founder of Nova Chief of Staff  

Maggie Olson is the Founder of Nova Chief of Staff, the premier and first-of-its-kind destination for Chief of Staff education, certification, and development. She has 20 years of experience in retail, food and beverage, and technology sectors and has held leadership roles at Nordstrom and T-Mobile. At T-Mobile, Maggie's impressive work led her to become the first Chief of Staff to the President of the T-Mobile Business Group. In this role, she built the Chief of Staff model from the ground up, creating a highly efficient team and establishing an executive back-office structure, supporting the President, SVPs, and over 5,000 employees. She also built a Chief of Staff team, defining all roles, processes, and systems. Through Nova Chief of Staff, Maggie continues to shape the future of business leadership, providing the tools and resources necessary for Chiefs of Staff to excel in their roles and drive company success.