Chief of Staff Resources: How to Excel in the Role
When I first stepped into the role of a Chief of Staff (CoS), I found myself scrambling to find relevant resources and information about this unique position. Whether I was looking for info on working with a Chief Operating Officer, honing the interpersonal elements of the CoS role, or learning to see strategically across different departments, information was scarce. There were bits and pieces here and there, but no centralized source of knowledge about the resources available for the role of Chief of Staff.
Fast forward a few years — I'd transitioned from being a private sector CoS to running my own executive coaching practice. A good chunk of my clients were Chiefs of Staff themselves or in similar roles, and I noticed a lot of the same questions came up as people worked to excel in their roles.
To help answer some of these common questions, I wrote my book An Insider's Perspective on the Chief of Staff. I also started my podcast Leveraging Leadership, which features interviews with Chiefs of Staff and their principals.
People would often ask me where they could find groups or cohorts of other CoS strategy pros. I'd point them toward various communities I'd come across, but I honestly didn't know much about them beyond their names at that point. Now, I’m very happy to say I've had the opportunity to get to know and interview many of the founders of those groups on my podcast and learn the unique perspectives, valuable insights, and primary focus each group offers.
If you're a new or aspiring Chief of Staff looking to expand your knowledge and network — or an experienced CoS seeking ongoing leadership development — this article will introduce you to some of the top Chief of Staff resources available today. While not an exhaustive list, these platforms offer a wealth of knowledge, training, and access to trusted peer communities to help you excel in complex situations and become a strategic partner to your executive team.
Ask a Chief of Staff
Founded by Clara Ma — a former CoS in Silicon Valley — Ask a Chief of Staff is a community platform for current and aspiring Chiefs of Staff. Some key offerings include:
Networking and mentorship opportunities with senior Chiefs of Staff
Webinars and workshops on relevant topics like effective communication, decision-making processes, and day-to-day operations
In-person events and meetups
Information about the latest job opportunities through their network connections
In my interview with Clara, she emphasized their focus on helping members find the right cultural and skill fit across different companies. The platform caters to both those new to the role and experienced Chiefs of Staff looking to level up their best practices.
Clara shared insights on how Ask a Chief of Staff supports members throughout their career journeys:
"We have two tiers of membership — aspiring and current. For our aspiring members, we focus on understanding the Chief of Staff role and building necessary skills. For current Chiefs of Staff, it's about building community, sharing resources, and continuing professional development."
One unique aspect of Ask a Chief of Staff is their approach to community building. Clara explained:
"We believe in the power of shared experiences. Our events and workshops are designed to foster real connections and facilitate peer learning, helping members gain a unique perspective on the challenges faced by Chiefs of Staff."
Chief of Staff Association
The Chief of Staff Association is a high-caliber, premium option for Chiefs of Staff seeking intensive professional development. While it comes with a higher price tag, the Association offers unparalleled opportunities for those who can take advantage of them. Key offerings include:
Immersive programs, including sessions at Oxford and Harvard
Annual membership with access to events and resources
Job board for Chief of Staff positions
Directory of CoS professionals
Blog with industry insights and best practices
I've spoken with Trent Smyth — the CEO of the Chief of Staff Association — and he's a great guy. I recently spoke with him and his Chief of Staff Jeremy Costa on my podcast. We talked a lot about the amorphous nature of the CoS role and how we can better define it. As Jeremy said:
“The superpower of a Chief of Staff is not having a job description because it allows them to go places where nobody else can. That allows them to be agile. It allows them to adapt their role to the needs of the organization.”
Trent noted that one of the Chief of Staff Association’s greatest strengths is the diversity of its membership:
“When you come to our programs or participate in our online forums, you have the ability to share your experiences and learn from people literally across the world — in different countries, but also in different organizations and backgrounds. That variety makes the conversation so rich.”
I've worked with many Chiefs of Staff who have gone through the Association's immersive programs, and I've consistently heard very positive reviews. If you're able to attend their Oxford program, it seems to be a transformative experience for many participants, offering valuable insights into becoming a great CoS.
While the Chief of Staff Association is one of the more expensive options available, the investment can be well worth it for those who can manage it. The caliber of networking, education, and professional development opportunities is top-tier, attracting senior executives and experienced Chiefs of Staff from around the world.
Chief of Staff Network
The Chief of Staff Network — led by Rahul Desai — is one of the longest-running CoS communities. Key features include:
Active Slack community with 900+ members globally
Weekly virtual events on leadership topics
In-person meetups and conferences
One-on-one member introductions and mentoring
Comprehensive salary data and reports
Rahul shared fascinating insights from their salary data on my podcast, highlighting factors that influence Chief of Staff compensation across company size, geography, and experience levels.
One of the standout features of the Chief of Staff Network is its global reach. Rahul noted:
"We have members from every continent, which provides a rich diversity of perspectives and experiences. Our Slack community is active every business day, with members sharing challenges, solutions, and opportunities, creating a truly trusted peer community."
The Network's salary reports are an invaluable resource for the CoS community. Rahul explained:
"We collect data from hundreds of Chiefs of Staff annually, giving us a comprehensive view of compensation trends. This information helps our members negotiate fair packages and understand their market value across different companies."
Chief of Staff Roundtable
Founded by Phil Burns, the Chief of Staff Roundtable focuses on peer learning and knowledge sharing. Offerings include:
Monthly roundtable discussions on key Chief of Staff topics
Peer learning cohorts for shared problem-solving in complex situations
Resource library with templates and guides, including sample job descriptions
On-demand coaching for professional development
Curated networking opportunities with senior executives
Phil's inspiration for starting the Roundtable came from his own experience of feeling isolated as a new CoS and seeking a trusted peer community, as he shared in our podcast conversation.
The Roundtable's approach is rooted in collaborative learning. Phil emphasized:
"We believe every Chief of Staff has valuable insights to share. Our roundtable format ensures everyone contributes and learns from each other's experiences, helping members become better strategic partners to their executive teams."
A unique aspect of the Roundtable is its focus on real-time problem-solving. Phil explained:
"In our peer learning cohorts, members bring current challenges they're facing in their Chief of Staff role. The group works together to brainstorm solutions, drawing on collective experience and creativity."
Nova Chief of Staff
Nova Chief of Staff — founded by Maggie Olson, a former corporate CoS at T-Mobile — offers a certification program and resources for aspiring and current Chiefs of Staff. Key components:
6-module self-paced certification course
Hands-on assignments and templates focused on best practices
Interviews with experienced Chiefs of Staff and senior executives
Industry-agnostic curriculum on core CoS functions
Ongoing course updates and new content on effective communication with team members and decision-making processes
When we spoke on my podcast, Maggie emphasized Nova's focus on practical, tactical skills that translate directly to on-the-job success.
The Nova certification program includes a structured approach to CoS education. Maggie shared:
"We cover everything from understanding the role of Chief of Staff to advanced skills like executive project management and strategic planning. Our goal is to give participants a solid foundation they can immediately apply in their work, helping them become great Chiefs of Staff."
Nova's course is designed to be accessible to a wide range of professionals.
"We've priced the course to be attainable for students and early-career professionals," Maggie noted. "We also offer lifetime access, so participants can revisit the material as they progress in their careers and take on more complex situations."
Chief of Staff vs. Executive Assistant
One clear and consistent takeaway from all my podcast interviews so far is that everyone I've spoken to emphatically agrees that a Chief of Staff is NOT an executive assistant. While both roles are crucial to an organization's success, they have distinct responsibilities and skill sets.
While a CoS handles high-level strategy and project management responsibilities, an executive assistant typically focuses on day-to-day administrative tasks. To be a great executive assistant requires talent and skill, which is a big part of why I’m so excited about my upcoming podcast interview with Hallie Warner of Force Multiplier.
Unlike the other resources in this guide, Force Multiplier is more geared to executive assistants than Chiefs of Staff. This year, Hallie and her team are launching The Force Multiplier Academy to help executive assistants become “influential leaders, strategic business partners, and confident Force Multipliers.” I’m looking forward to chatting with Hallie about the Academy and much more on our upcoming podcast episode!
Choosing the Right Resources
With several great options available, how do you decide which resources are right for you? Consider factors like:
Your current career stage (aspiring, new, or experienced Chief of Staff)
Specific skills or knowledge areas you want to develop (strategic plans, data analysis, etc.)
Preferred learning formats (online courses, live events, peer discussion, etc.)
Budget and time commitment
Geographic focus (some groups have a stronger presence in certain regions)
Industry specificity (some resources cater to particular sectors or company types)
Additional Resources
In addition to these dedicated Chief of Staff platforms, don't forget to check out:
Industry-specific associations related to your company or sector
Executive education programs at top business schools (many now offer CoS-specific courses)
LinkedIn groups focused on Chiefs of Staff, such as the Chief of Staff Forum
My podcast: Leveraging Leadership
It's worth noting that I have an upcoming podcast guest who will be sharing his experience going through the McChrystal Group's Chief of Staff program, which should be a lot of fun — I’m looking forward to learning more about that one!
I'll update this page as I discover more useful resources, so check back periodically. You can also join my newsletter for updates, including notifications when I add new resources to this guide.
If you know of any other great Chief of Staff resources I'm missing, please shoot me a message. If you have questions about any of the resources or people mentioned here, please let me know as well — I'm happy to answer or provide any helpful information I can.
Conclusion
The Chief of Staff plays an evolving role across the business world. By tapping into these valuable communities and tactical resources, you'll be well-equipped to thrive in this dynamic and impactful position.
Remember, the journey of a Chief of Staff is one of continuous learning and adaptation. Embrace the wealth of knowledge and years of experience by connecting with your peers and leveraging the resources available to you. Seek out professional growth systems and never stop pursuing new ways to enhance your skills and expand your impact as a strategic advisor to your executive team.
Whether you're just starting out or you’re a seasoned CoS looking to take your performance to the next level, there's a resource out there to support your growth. Invest in yourself, leverage these platforms, and transform yourself into an even more effective and influential Chief of Staff — one capable of navigating complex situations and driving decision-making processes in your organization.
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.