Is Chief of Staff a Good Role?
The short answer? Yes! The slightly longer answer? It depends.
The Chief of Staff (CoS) role can be a potentially career-defining position in today’s business world, but whether it’s a good role for you depends on what you’re looking for and where you are in your career. For some, it’s a fulfilling, long-term, behind-the-scenes role or a powerful launchpad into an executive leadership position. For others, it’s ambiguous, confusing, and overwhelming — in other words, a bad fit.
By digging into the details of the role of Chief of Staff, you can better understand whether you’d be a good fit in this complex, rewarding position.
When the Chief of Staff Role Can Be a Great Fit
The Chief of Staff position has heavy involvement in strategy, execution, and relationship-building. It’s the connective tissue between the Chief Executive Officer (CEO) or other senior executives and the broader organization. This crucial role involves managing special projects and aligning various teams and timelines to focus on the right strategic priorities.
If you identify with the following statements, the CoS role might be your C-suite sweet spot.
You Like Being in the Room, But Don’t Crave the Spotlight
Chief of Staff is a perfect role for someone who enjoys working behind the scenes. You might participate in board meetings, shape strategic initiatives, align the executive team, and influence major decisions — all without necessarily taking credit.
One CoS I coached referred to himself as a “hero maker.” In other words, the job isn’t to be the hero yourself, but to make your principal (often the CEO of the company) and others on the executive leadership team look like heroes.
You Can Work Across Various Functions and Time Horizons
Being a Chief of Staff often means operating on multiple timelines at once. One minute, you’re putting out immediate fires related to daily operations, while the next, you’re planning next quarter’s town halls or doing strategic planning for next fiscal year.
You’ll likely interface with nearly every department — product development, sales, HR, finance, legal, etc. — so being good with people is a must. You don’t necessarily need to be an extrovert or even like being around people, but you need to be able to navigate a wide range of strong relationships. It’s essential to be able to zoom out to a 30,000-foot view while also overseeing specific functions and department heads on the ground.
You’re a Flexible Professional With Strong Strategic Thinking Skills
A great Chief of Staff isn’t always the deepest technical expert in the room, but they also don’t need to be. The role often requires a generalist who can streamline operational efficiency and make smart decisions in ambiguous situations. You will not always have the full picture when you need to make a call, and you have to be okay with that.
Being a CoS can also be a great way to gain hands-on, front-row-seat experience with all departments across the entire organization. Some people use the CoS position as a springboard into the Chief Operating Officer (COO) role or other executive positions. In fact, some larger companies treat the CoS as a rotational role for 18-24 months, redeploying Chiefs of Staff as vice presidents after their rotations.
In short, whether you’re just starting out or you already have years of experience in the role, adaptability is one of the key skills for a CoS.
You Operate With a Mix of Adaptability and Influence
To be a good Chief of Staff, you’ll need to think on your feet while balancing various personalities and leadership styles. A Chief of Staff can bring teams together and anticipate their needs. This critical role requires genuine curiosity, a proactive mindset, and the ability to read people.
An important aspect of this adaptability is effective task switching to maximize your valuable time. Try to batch your tasks whenever possible and keep the company focused on key goals without wasting time winding up or down from task switching.
Interpersonal skills are vital, as is the ability to lead through influence rather than direct authority. You should strike a balance between speaking truth to power and knowing when to hold your tongue for the greater good.
It’s this combination of influence and flexibility that makes the Chief of Staff an all-in-one role as a strategic advisor, sounding board, and trusted partner to the CEO.
[Looking for more valuable insights into the Chief of Staff role? Check out my podcast, Leveraging Leadership. Every week, I feature interviews with Chiefs of Staff and their principals, sharing fresh perspectives and best practices for any leader looking to grow their career.]
When the Chief of Staff Role Might Not Be for You
Of course, the role of the Chief of Staff isn’t for everyone. It comes with unique challenges that can be draining for people with different working styles or career goals. Even if you’re doing all the right things, the wrong attitude can sink your ship in a hurry.
If the following statements sound like something you’d say, you might want to steer clear of CoS roles.
You Value Consistency, Stability, and Predictability
The day-to-day operations of a Chief of Staff can vary widely, as the role has many different functions. One day might involve project management for a new product launch — the next day, you’re preparing materials for a board meeting or tackling a thorny personnel issue.
The CoS plays a vital role during times of growth and change, helping provide smooth transitions through anything from digital transformations to change mandates. These transitions can be tough times without clear leadership, and the Chief of Staff needs to remain focused through unpredictable and turbulent waters.
Here’s an example to marinate on: I talked to a CoS who planned a project for weeks, got stakeholder buy-in, and developed a full outline for a project plan with milestones. Then, Monday morning rolled around. Due to market shifts and changing internal priorities, the principal changed their mind and asked the Chief of Staff to tackle a different time-sensitive opportunity instead.
Are there times when you need to push back, challenge your principal, and make sure the team isn’t blowing with the wind at every shiny object? Of course. That said, there are also times like the one I just outlined when you have to scrap everything and move in a different direction - and you have to be okay with that. If you’re not, CoS isn’t for you.
If you thrive on clear key performance indicators (KPI), tangible work products, and predictable deliverables, this may not be the right role for you.
You Need to Be in Charge
Some people are born to lead. They love overseeing lots of direct reports from various team members, being an authority figure within the organization, and having the ultimate responsibility as the final decision-maker. You always need someone to assume this role, but it’s not the Chief of Staff. The CoS focuses on the principal’s needs before anything else.
The Chief of Staff serves as a conduit for the chief executives and often works through others rather than directly managing them. Your strategic vision and communication skills are your levers of influence and control, not a formal org chart.
You Struggle With Boundaries or Feedback
As the Chief of Staff, you’ll be part of tough conversations, strategic decisions, and competing priorities. That means that people will be unhappy with you (it’s not a might, it’s a 100%-certain will). If you tend to internalize negative feedback or avoid conflicts, the role of CoS can be emotionally exhausting.
The Chief of Staff also needs to be willing and able to speak up with contrarian viewpoints. Keep in mind that you need to fiercely protect both your own time and your principal’s. If you wait for permission, struggle to set boundaries, or require external validation to make decisions, this role could absolutely crush you.
You’re Looking for a “Lifestyle” Job
This isn’t a 9-to-5. You will never get to kill the clock or phone it in. In particular, startups and tech companies move fast, and your principal will expect you to task switch, juggle multiple priorities, and keep the company focused on strategic goals…all without burning yourself out.
The Chief of Staff role is much more than just a glorified executive assistant (EA) position. While the EA focuses more on administrative tasks, the CoS role’s responsibilities can be an exhaustive list. If you need work-life balance to take center stage, stepping into a CoS position may not be a great idea.
You Want Fame and Glory
You can certainly make great money as a Chief of Staff. That said, if your top priority is to make as much money as you can for the lowest amount of work, this is not your gig. It’s also not for you if you want to be the center of attention and get full credit for everything you accomplish. The CoS operates behind the scenes, making other people look good.
Simply put? When you’re the Chief of Staff, it’s not about you. If you need to be the center of attention, go do something else!
Reach Your Next Level With These Chief of Staff Resources
The CoS position can be tricky to navigate. The good news? There’s help available if you need it.
If you’re interested in becoming a Chief of Staff — or you’re already a CoS and want to be a better one — there are plenty of valuable resources out there. Here are a few I recommend:
My book, An Insider’s Perspective on the Chief of Staff: Why You Need One and How to Be a Great One, is an in-depth exploration of the Chief of Staff role. It includes plenty of tips and tricks to help CEOs optimize the CoS position and help Chiefs of Staff become the best versions of themselves.
Tyler Parris also has a great book for Chiefs of Staff called Chief of Staff: The Strategic Partner Who Will Revolutionize Your Organization. Based on interviews with Chiefs of Staff and their principals, Tyler breaks down this essential role and the value it provides to both small and large organizations.
Joining a peer community with other current and former CoS professionals can be incredibly helpful. You can really expand your knowledge and enhance your leadership development in these cohorts. These CoS resources — including the Chief of Staff Association, Ask a Chief of Staff, and more — also provide unique opportunities for networking, as you’ll get to bounce ideas off of other high-achieving Chiefs of Staff.
Chief of Staff coaching can be highly beneficial, whether you have previous experience in the role or you’re tackling it for the first time. The Chief of Staff title means different things at different companies — the role is a juggling act, and the Chief of Staff job description can be annoyingly vague. The right executive coach can help you maximize your contributions and minimize your frustrations.
Executive coaching is also a great idea for new CEOs, VPs, directors, senior managers, and similar roles. Having a coach in your corner can be a big help, especially when you’re getting your feet wet in a new role.
In addition, feel free to book a call with me if there’s anything you need to talk through! I can help you find a solution, or at least point you in the right direction.
About The Author
Emily Sander is a C-suite executive turned leadership coach. Her corporate career spanned Fortune 500 companies and scrappy start-ups. She is an ICF-certified leadership coach and the author of two books, An Insider’s Perspective on the Chief of Staff and Hacking Executive Leadership.
Emily works with early to senior executives to step into effective leadership with one-on-one coaching. Go here to read her story from seasoned executive to knowledgeable coach.