In the latest episode of Scaling Stories, we had the pleasure of speaking with Scott Amenta, Founder of the Chief of Staff Network and Sylva. Scott’s unique journey—from his time at Foursquare and Techstars to becoming one of the first Chiefs of Staff at Spring—has given him unparalleled insights into what it takes to excel in the Chief of Staff role. Today, Scott is empowering a global community of Chiefs of Staff through his work at the Chief of Staff Network and scaling more unique communities through his work at Sylva.
In this post, we are summarizing the key learnings from our conversation about what it takes to excel as a Chief of Staff, how to increase your principal’s impact and the actionable steps Chiefs of Staff can take today to make sure they thrive in this role and add real value to their organization.
What It Means to Be a Chief of Staff
Scott emphasized that the Chief of Staff role is more than just an operational position—it’s a leadership role that requires a deep understanding of the organization’s vision and how to execute it. Whether it’s scaling teams, driving strategy, or aligning internal operations, a Chief of Staff’s impact extends across all departments. They act as the executive’s right hand, ensuring that the executive time is spent on the most critical activities, while also driving initiatives independently.
What’s the Difference Between a Chief of Staff and an Executive Assistant?
A Chief of Staff and an Executive Assistant are on the same team and their key objective remains the same – make sure they increase the impact of their executive within the organization. However, they way they operate and achieve this objective differs.
An Executive Assistant (EA) focuses primarily on managing the executive’s day-to-day tasks, ensuring their time is spent efficiently and handling logistical details such as scheduling meetings, coordinating travel, and managing communication. The EA ensures that the executive’s time is optimized, allowing them to focus on high-priority items.
In contrast, a Chief of Staff (CoS) operates at a more strategic level. While they may support some operational tasks, their primary responsibility is to drive larger organizational goals by working cross-functionally, managing key projects, and acting as a liaison between the executive and other departments. A Chief of Staff helps scale the executive’s impact by shaping the overall strategy, ensuring alignment across teams, and implementing systems that allow the company to grow more efficiently.
In short, while an EA maximizes the executive’s time, a Chief of Staff amplifies the executive’s broader vision and organizational influence.
Key Skills Needed as a Chief of Staff
Scott admits that being great as a Chief of Staff often comes down to being flexible and leaning into what the organization needs, rather than developing certain hard skills. Chiefs of Staff come from all kinds of backgrounds and tend to be generalists rather than specalists.
One of the recurring themes in Scott’s conversation was the importance of building trust. A Chief of Staff must establish a strong foundation of trust with the executive and key stakeholders across the organization. This requires emotional intelligence, clear communication, and the ability to navigate complex relationships. Trust is also built by being a reliable problem-solver—someone who steps in to ensure projects move forward without the executive needing to be involved in every detail.
How to Excel as a Chief of Staff
A critical responsibility for any Chief of Staff is ensure the executive’s vision is carried through the organization. Scott explained that Chiefs of Staff must focus on freeing up their executive’s time for strategic initiatives while tracking the impact of the actions taken by the leadership team.
Spend Time with Your Principal
Scott admits that the Chief of Staff role is unique and highly depends on the personality and work style of your principal. Make it a priority to get to know your principal, their strengths and weaknesses, and think of how you can best complement them. The stronger the relationship, the more effectively you’ll be able to represent them and amplify their impact within the organization.
Build Strong Relationships and Trust
Cultivating trust with your principal and other leaders in the organization is the foundation for driving any impact in the organization. Take time to understand the needs of the executive team and ensure open, honest communication. Strong relationships are the backbone of a successful Chief of Staff.
Leverage a Network of Peers
Search for communities of peers that you can both benefit from and pass your knowledge to. In search of peers, Scott went on to found the Chief of Staff Network, which connects thousands of professionals today. Connect with other people who are navigating similar challenges.
Understand the Organizational Pulse
Spend time getting to know how different departments operate. A Chief of Staff’s role involves cross-functional collaboration, so invest in understanding the dynamics of the teams you work with and how you can support them.
Be Ready to Step into Different Roles
Scott mentioned that a Chief of Staff often needs to play multiple roles, from coach to facilitator. Be flexible and ready to adapt based on the organization’s needs, ensuring you can step in and support where necessary.
Pro Tip from Tackle: Take a deep dive into your executive’s calendar. Are their meetings aligned with strategic goals? Identify time-consuming activities that can be delegated or eliminated to ensure their focus stays on high-impact initiatives. Regular calendar audits help both the principal and their closest allies ensure alignment between everyday actions and organizational goals.
Top Resources to Support Your Growth
For those looking to become a Chief of Staff or improve in the role, Scott recommended focusing on soft skills, like emotional intelligence and trust-building, just as much as hard skills. The ability to pivot between strategy, execution, and relationship management is what makes a great Chief of Staff. The closest allies of executives are often measured by how well they ensure alignment between executive priorities and organizational goals.
Stratechery by Ben Thompson – A newsletter and podcast offering macro insights into the tech industry, including companies like Amazon, Google, and Facebook.
A Media Operator – A newsletter focused on the media industry, communities, and how to build and grow them.
The Innovator’s Solution – A book about first principles thinking and innovation, particularly useful for Chiefs of Staff.
Chief of Staff Network – A community with a wealth of public resources, including a podcast, knowledge hub, and research related to Chiefs of Staff and operators.
