Top 8 Chief of Staff Mistakes (and How to Avoid Them)
The Chief of Staff role has continuously evolved over the last decade. Today’s Chief of Staff is a strategic partner for the leadership team and a force multiplier for the senior executive they directly support. When leaders set the Chief of Staff up for success, this important role can make a huge difference in the company’s pursuit of executives’ goals.
However, even in today’s competitive landscape, the CoS role is still relatively undefined in some organizations. In fact, many of the top mistakes Chiefs of Staff make stem from unclear expectations.
With this in mind, I’ve created this guide to some of the most common leadership mistakes made by Chiefs of Staff, and what the best ones do instead.
Mistake #1: Treating the Role Like a Glorified Executive Assistant
One of the most common pitfalls for Chiefs of Staff is executing the role like a more senior version of what executive assistants (EAs) do. While EAs and Chiefs of Staff often collaborate and frequently share the same direct report, their roles are entirely different.
If a CoS is too heavily focused on administrative issues, they may miss the opportunity to provide strategic input and help make their executive a better leader. A great Chief of Staff helps leaders strategize and contextualize major decisions, keeping the entire org focused on the executive team’s common goals. Administrative tasks like taking phone calls and booking travel are part of an EA’s job.
How to Avoid It
Own your role by clearly defining it from the start and setting yourself apart from the EA’s responsibilities. If you’re a new hire at a company without a clear Chief of Staff job description, an experienced business coach can help you set reasonable guardrails and expectations.
Mistake #2: Failing to Build Credibility in the C-Suite
A Chief of Staff can’t be effective without building trust across the leadership team. Whether a company has a relatively new CEO/founder or a team of seasoned business owners calling the shots, a lack of credibility will always be a major problem area for a Chief of Staff.
This is especially risky for someone stepping into the role for the first time. If executive team members don’t respect the Chief of Staff’s opinion or trust them with sensitive information, it’s essentially impossible for the CoS to do their job.
How to Avoid It
The best way to build credibility with executives is to display consistency and discretion from the start. Providing constructive feedback, keeping confidential information to yourself, and thinking several steps ahead go a long way toward developing trust. In short? Say what you’re going to do, and do it.
Mistake #3: Betraying Your Colleagues’ Trust
It’s important for a CoS to focus heavily on strategy and execution, but not at the expense of relationship-building. The Chief of Staff is often a trusted confidant for the principal and others — those other people might say things to the CoS that they wouldn’t say to the principal.
There’s a fine line between informing your executive of general trends in employee attitudes and selling out your colleagues. If a team member says something that absolutely needs to be passed on, you need to frame it in a way that protects and respects them.
Additionally, the Chief of Staff may be privy to sensitive discussions about discrimination claims, HR complaints, and legal issues. The CoS also often knows about major initiatives like mergers, acquisitions, and re-orgs before they’re finalized. Don’t go blabbing about your CEO’s plans before they’re set in stone.
How to Avoid It
Clear communication and maintaining trust are incredibly important leadership skills, and in many situations, they matter more than your qualifications and experience. Pay close attention to employee engagement and become a trusted individual, both with those above you on the org chart and those below you.
Mistake #4: Not Knowing When to Be a Decision-Maker Instead of a Decision-Supporter
Some people think that the Chief of Staff simply executes other people’s ideas. While this is certainly a large part of the job, the CoS also needs to be able to make their own decisions, especially if their direct report is a new leader or first-time manager.
For example, the Chief of Staff might decide which initiatives require the executive’s attention. Or, they might determine how to sequence projects, fast-tracking time-sensitive matters while pushing less important measures to the back burner.
It’s important not to simply become a “yes person” rubber-stamping everything that comes your way. You need to share your thoughts and opinions, but also be able to execute the original idea if you’re overruled. It’s a tricky balance!
How to Avoid It
Keep your ego in check, but maintain confidence in your skills. Acting like you have more authority than you do is a great way to introduce friction between yourself and leadership, but you didn’t become a CoS by being a parrot with no thoughts of your own.
Mistake #5: Lacking the Backbone to Speak Up
For a Chief of Staff, simply capitulating to leadership will lead to poor performance more often than not. Do you have the courage to have difficult conversations with leadership? Can you challenge a senior executive’s ideas while still demonstrating professional and personal respect? Can you provide less-than-positive feedback without feeling exposed?
If you let the C-suite executives walk all over you, they won’t respect you enough to value your input. At the same time, messaging and communication style are super-important, because you don’t want to get pushy either. Many people can’t strike this balance, which is a big part of why many people aren’t cut out to be Chiefs of Staff.
How to Avoid It
Great leaders have courage, and they know how and when to say the right things to get the results they want. With this in mind, the best way to avoid Mistake #5 is to pick your battles. Say something when something needs to be said, don’t just speak up to get your voice in the mix. Practicing “radical candor” can be a great way to hit the sweet spot between being too blunt and too reserved.
Mistake #6: Not Carving Out Time for Deep Thinking
Some Chiefs of Staff get so overloaded with tactical work that they spend their entire day bouncing from meeting to meeting, never setting time aside for deep work. This is a classic trap in high-growth environments, especially those navigating frequent change.
It can feel like there are too many tasks at hand to set out dedicated time for brainstorming and conceptualizing, but without it, Chiefs of Staff often have the dreaded “high-activity, low-impact” combo. In the long term, you’ll be better off if you have dedicated time for brainstorming and conceptualizing.
How to Avoid It
The best Chiefs of Staff protect time for strategic thinking. If you’re a time-blocker, block out specific “deep thinking” time at least once a week. It doesn’t have to be a ton of time or on a daily basis, but merely committing yourself to it can help you develop new skills and bring a fresh, unique perspective to the table.
I actually discussed this very topic as a guest on a recent episode of The Chief of Staff Podcast! Give it a listen for more insights on how to approach this delicate balancing act.
Mistake #7: Assuming You’re Not Qualified to Be a Chief of Staff
Quite a few Chiefs of Staff come into the role with prior success in management positions, but many don’t. The right person for the job isn’t always obvious, as it requires a unique blend of skills. But just because you lack prior experience in directly comparable roles doesn’t mean you’re not a good fit for the position.
Do you have cross-departmental experience? Do you have a strategic eye? Can you provide context for your opinions? Can you communicate up, down, sideways, and diagonally across the organization? Are you organized and proactive? These things matter much more for prospective Chiefs of Staff than “I held this specific title for this amount of time.”
How to Avoid It
There is no rigid career path that leads to a CoS role, and you don’t need previous Chief of Staff experience to be successful. Commit yourself to consistently and intentionally building your Chief of Staff toolkit. Remember that what you did before stops mattering, more or less, as soon as you step into this role.
Mistake #8: Failing to Build a Shared Language and Evolve With Your Role
As a new Chief of Staff, you need to have a relationship-building conversation with your principal either before you start in the role or immediately after you get into it. The Chief of Staff and their principal need to develop unified goals and a vision for how they’re going to execute them.
In addition, it’s important to make sure you’re on the same page regarding your role and responsibilities. Remember that the Chief of Staff isn’t a rigid role with easily defined parameters, and that it can shift and expand as you go.
How to Avoid It
The initial conversation is always vital, but it’s also important to revisit this discussion over time. Not only can a Chief of Staff’s responsibilities shift and evolve, but so can a principal’s. Schedule regular check-ins with your principal to align your perspectives and make sure you’re maximizing your value.
Minimize These Mistakes, Maximize Your Impact
The most important thing to keep in mind is that mistakes are inevitable in any role, but being aware of these eight common missteps can help make you the best business leader possible in the CoS role. Supporting your principal is always the #1 priority for a Chief of Staff, but it’s also important to set clear objectives for yourself and develop your own leadership style.
Being a great Chief of Staff is about more than just executing effective meetings and driving key results. It’s also about handling yourself in a way that makes top talent want to work alongside you to pursue the CEO’s vision.
It’s Easier with a Coach in Your Corner
Executive coaches can be invaluable resources for Chiefs of Staff, helping navigate the complex strategic and interpersonal demands of the role. If you’re struggling with any of the common issues discussed here, let’s schedule an intro call and discuss how I can help.
I’ve worked with a wide range of Chiefs of Staff, including business leaders at Fortune 500 companies, fractional Chiefs of Staff at scrappy startups, federal workers with government agencies, and more. If you’re concerned with any of these eight potential pitfalls, let’s work on an action plan to help you avoid these mistakes and achieve your goals as a CoS.
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.