Why Every Healthcare Leader Should Rethink the Chief of Staff Role: Lessons from Maggie Olson, CEO & Founder at Nova Chief of Staff

In today’s rapidly shifting healthcare environment, C-suite executives are searching for every lever to drive efficiency, effectiveness, and strategic focus. Yet many healthcare leaders remain unaware of a game-changing role that’s quietly transforming industries from tech to retail—and now, healthcare: the modern Chief of Staff.

On a recent episode of The American Journal of Healthcare Strategy podcast, host Cole Lyons sat down with Maggie Olson, MBA—CEO & Founder at Nova Chief of Staff—to explore why the Chief of Staff role is exploding across sectors, how it differs from traditional executive positions, and what it means for overloaded healthcare leaders trying to do more with less.

Olson, who built her career in tech, retail, and customer experience before founding Nova, offered a perspective that’s both refreshingly candid and deeply practical. “The Chief of Staff role spans across all industries, sectors, sizes… Healthcare is definitely one of them,” Olson explains. In an industry where regulatory pressure, burnout, and complex change are the norm, understanding and implementing this role could be a critical unlock for organizations at every stage.

What Is a Chief of Staff—and Why Should Healthcare Executives Care?

A Chief of Staff is a strategic right hand to executive leaders, focused on maximizing the leader’s effectiveness, driving initiatives, and enabling top-level strategy—not just administrative support.

Healthcare leaders are well-acquainted with the grind of calendar management, endless meetings, and operational firefighting. But as Olson points out, “Business leaders have long known that they need administrative support… But what’s really exciting is an increase in the awareness of the need for strategic, executional support to assist those leaders.”

In practical terms, a Chief of Staff:

• Acts as a strategic thought partner, not just a scheduler.

• Manages and drives alignment across leadership teams.

• Leads key initiatives and often acts as a proxy for the executive.

• Frees up the leader to focus on vision, growth, and high-level strategy.

This is especially relevant in healthcare, where executives are routinely pulled into tactical matters at the expense of mission-critical, long-term work. As Olson puts it, “If you are constantly heads down chasing deliverables and managing projects that just seem like it’s not what you should be spending your critical time on… that’s when you need to identify that you could use Chief of Staff support.”

Chief of Staff vs. Executive Assistant vs. COO: What’s the Difference?

The Chief of Staff is neither an administrative assistant nor a redundant C-suite position—they occupy a unique, strategic seat focused on executive enablement and cross-functional leadership.

Many organizations, especially in healthcare, confuse these roles, leading to inefficiency and lost opportunities for leverage. Olson clarifies the distinction:

• “A Chief of Staff is not an administrative role, although they should be in the loop on everything.”

• Executive Assistants (EAs) handle logistics—calendar, travel, expenses. Chiefs of Staff do not.

• COOs operate on behalf of the company, with their own teams and scorecards.

• Chiefs of Staff serve the leader as a person, driving forward that executive’s projects, initiatives, and priorities.

Olson emphasizes: “The roles do not overlap… all three of you are truly partners between the business leader, the EA, and the Chief of Staff.”

Key differences:

• EAs = logistics & admin | Chiefs of Staff = strategy, project management, cross-functional leadership | COOs = company-wide operations, independent objectives.

“The Chief of Staff role can exist at a lot of different leadership levels… As the Chief of Staff is more senior, you’re going to see them feeling a little bit more of that proxy role, a little bit more of that advisor role to the business leader.”

When Does an Organization Need a Chief of Staff?

You need a Chief of Staff when an executive is spending too much time (over 30%, according to Olson) on tactical, operational tasks instead of vision, growth, and strategy—even after administrative support is in place.

Olson is direct: “If you are finding that you’ve got a ton of ideas, nowhere for them to land, that you’re being pulled in a ton of different directions… and you already have an admin, I always recommend admin first… then that’s when you need a Chief of Staff.”

Signs you need a Chief of Staff:

1. Executive is bogged down in projects, not strategy.

2. Special initiatives languish or get lost.

3. Leadership team struggles with alignment.

4. EA is being stretched into strategic projects and burning out.

5. Organization is growing, but cross-functional complexity increases.

This pattern holds regardless of sector or size. Olson notes, “There are Chiefs of Staff in education, in nonprofit, in high-net-worth, in big business and small business… with an awareness gap. You’ll walk into any of those places and they may have never heard of a Chief of Staff.”

Why Stretching Your EA Into Chief of Staff Duties Fails

Merging EA and Chief of Staff roles leads to burnout, role confusion, and a failure to maximize either administrative or strategic work.

It’s tempting—especially in resource-constrained environments like hospitals—to “just have the EA handle it.” But Olson is blunt: “When you combine the two, you’re not going to do either well… Admin work is a full-time job.”

Risks of conflating EA and Chief of Staff:

• EAs lose capacity for crucial admin tasks.

• Strategic projects receive inconsistent attention.

• Respect and credibility for both roles suffer.

• Neither tactical nor strategic work gets done at the highest level.

Olson shares, “It’s very difficult from a positioning perspective for the EA to have the respect of a Chief of Staff… It’s also very difficult to find the time, physically and mentally, to dedicate to larger strategic problems.”

Titles, Structures, and Organizational Fit: Does Your “Chief of Staff” Need That Title?

The Chief of Staff role is defined by function, not title—it may exist as “Special Assistant,” “Director of Operations,” or “Project Manager” depending on your organization.

In healthcare, the “Chief of Staff” title often refers to a senior physician, which can create confusion. Olson explains, “There are over 20 or 30 different titles in use for the role of Chief of Staff and it’s almost less important… It’s really important to understand the work you are doing as Chief of Staff work.”

Look for Chief of Staff functions, regardless of title:

• Board materials preparation.

• Executive communication, talking points.

• Leading special projects or initiatives.

• Cross-functional alignment.

If your organization is “doing the work” but calling it something else, you may already have the function—just without the structure or best practices.

“It’s about identifying who is that business leader’s support person… and what are the things that, kind of behind the scenes, that Chief of Staff-esque role is filling.”

Building Trust: How to Onboard and Integrate a Chief of Staff

The Chief of Staff is a high-trust role, best built through internal networks or transparent onboarding—requiring deep executive access, clarity of purpose, and ongoing communication with the leadership team.

Olson stresses that “It is such a high-trust role… one of the reasons why Chiefs of Staff are often hired internally or within the network that you already have.” But external hires are common, and successful onboarding follows a few key steps:

Best practices for integrating a Chief of Staff:

1. Communicate clearly to your team: Explain that the Chief of Staff complements, not replaces, the EA.

2. Provide deep access: Let them shadow, review calendars, and observe decision-making.

3. Model partnership: Attend key meetings together before delegating fully.

4. Elevate the Chief of Staff publicly: Give them visibility and endorse their authority.

5. Solicit feedback and adjust: Encourage the team to provide input during the transition.

“How you position your new Chief of Staff to your executive team is really critical—it’s not just a one-time announcement, it’s continual change management,” Olson notes.

How Chiefs of Staff Help Executives—and Organizations—Scale

A Chief of Staff enables executives to operate at a higher level by filtering noise, aligning teams, driving cross-functional initiatives, and ensuring leaders focus on what matters most.

Olson shares her personal experience: “My Chief of Staff was my third full-time hire… I’m great at [executing], but I can’t be there right now. I need to be in the vision and growth space.”

For healthcare executives juggling clinical, academic, and leadership duties, this is not a luxury—it’s a necessity. “I think of having a Chief of Staff as something so important… I can just imagine some of the leaders I’ve spoken with, right now they go and practice emergency medicine, lead the organization from a CEO perspective, and also are a professor… You need a Chief of Staff to be that extra layer.”

A Chief of Staff:

• Understands executive priorities.

• Analyzes and recommends time management changes.

• Designs and implements systems to reduce redundancy.

• Ensures meetings and projects align with strategic goals.

• Acts as a buffer, proxy, and force multiplier.

Olson highlights, “Chiefs of Staff are very good at figuring out what the problem is, learning quickly, being curious, getting something done… in such a huge breadth of categories.”

Professional Development: Nova Chief of Staff and the Path to Certification

Nova Chief of Staff offers a comprehensive certification program—over 50-60 hours, self-paced—preparing aspiring Chiefs of Staff with hands-on training, strategic skills, and real-world assignments.

Olson’s company, Nova Chief of Staff, launched its certification to fill the capability gap in this high-impact role. “We’ve got over 500 students across 22 countries enrolled in our course… even happier when I hear it’s so well received in the market.”

Program highlights:

• 50-60 hours of self-paced online content.

• Assignments simulate real Chief of Staff responsibilities.

• Designed for both company-funded and self-funded students.

• “Probably upwards of 50 or 60 different folks in our course from the healthcare sector… We’d love to have anybody listening send their folks through.”

The program is priced to be accessible—currently $1,450, rising to $1,850 in January 2025—and fits within most tuition reimbursement programs, even at major institutions like Penn and Jefferson.

Olson urges leaders: “Often their next Chief of Staff might be sitting right in front of them… Not all executive assistants are going to make a great Chief of Staff, but you’re going to know the ones who would.”

Takeaway: Chief of Staff as a Catalyst for Healthcare Leadership

For U.S. healthcare leaders facing relentless pressure, the Chief of Staff role is more than a trend—it’s a strategic imperative. As Maggie Olson’s experience and Nova’s success make clear, investing in this function pays dividends in clarity, focus, and organizational resilience. Whether you call the position “Chief of Staff,” “Director of Operations,” or something else, what matters is empowering a strategic partner who keeps your eyes on the horizon while handling what’s on your plate.

“It’s been so fun meeting folks in our course from the healthcare sector and hearing about the company structures and problems they’re solving… I hope we see more and more Chiefs of Staff in the coming months,” Olson concludes.

Actionable Insight:
If you’re an executive leader spending more time on operations than strategy—even with great admin support—consider whether a Chief of Staff could unlock your next phase of growth. Identify the untapped talent in your ranks, or look to expert-driven programs like Nova to build this critical capability. Your leadership legacy—and your organization’s future—may depend on it.