The seven things a corporate Chief of Staff does

Posted March 9, 2022 | View revision history

The Chief Of Staff role is often poorly understood and difficult to define. Before becoming one myself, I had little appreciation for the role beyond watching fictional characters like Leo McGarry and Josh Lyman on the West Wing,1 but as I’ve been settling into this new-to-me role, I’ve been thinking critically about what a corporate Chief of Staff does day-to-day and how they uniquely bring value to their principal or executive (whom I’ll generally call “CXO” here2) and to the organization they support.

At a high level, I’d break down a Chief of Staff’s responsibilities into three key parts:

  1. Tactical - Program management, communication, execution, and operations
  2. Strategic - Stewardship of strategy, planning, vision, and culture
  3. “Everything else” - Serving as advisor, confidant, broker, and generally doing what needs to be done

Adding to the confusion, the Chief of Staff function is unique in that the scope, responsibility, and impact can grow dramatically over time from the tactical to the strategic based on the maturity of the organization the Chief supports and the seniority of the individual in the role. Whether you’re entering the role yourself or are working with a corporate Chief of Staff for the first time, in order from most tactical/junior/immature to most strategic/senior/mature, here are the seven things a great Chief of Staff does:

1. Manage the office of the CXO

At the most basic level, the Chief of Staff is responsible for managing the “office of the CXO”. At GitHub, my team fittingly refers to this as the organizational “operating system”, which the Chief is responsible for installing, configuring, monitoring, upgrading, and patching to keep everything running bug free. In this way, the Chief’s “software”, and by extension, the Chief themselves help the business operate more efficiently by scaling the efforts of its leaders and membership. The specific activities will vary depending on the business unit the Chief is supporting, but generally, one would expect this meta work3 to include managing:

  • “Rhythm of the business” - Establishing, documenting, and maturing repeatable processes for critical business functions that occur on a regular cadence like budget planning, strategic planning, headcount planning, along with the overall planning and execution tempo of the organization.
  • Office operations - Partnering with human resources, talent acquisition, procurement, and legal among other teams to ensure the organization’s smooth operation. This may also include being responsible for diversity, engagement, morale or other initiatives, as well “owning” contracts, vendor agreements, and purchase renewals that don’t naturally fit into other functions.
  • Internal, external, and executive communications - Compiling regular updates on business activities to generate cross-team awareness; running monthly all hands, lunch and learns, demo days, and other points of contact; reporting up for leadership or board reviews; preparing the CXO for conferences, events, interviews, presentations, and other engagements; and generally managing the overall “front door” of the organization to the rest of the company through documentation, process, and other established (and thanks to the Chief, streamlined) interfaces.

As a CXO’s office matures, this may begin as an office of one (the Chief), but can quickly grow to three or more individuals, whom the Chief is expected to manage to extend their own reach and impact.

2. Improve organization effectiveness

If there’s one thing that describes the value a Chief of Staff brings to an organization, it’s “effectiveness”. Unlike other roles, it’s not enough for the Chief themselves to be effective, but rather they are expected to improve the effectiveness of the CXO, the organization’s leaders, and the business as a whole. Specifically:

  • CXO effectiveness - Serving as a formal and informal gatekeeper to ensure that the CXO is spending their time on the right things. The Chief has the sense to know what to keep “front of mind” for the CXO, and what falls into “I’ll let you know to get involved” territory.
  • Leader effectiveness - Improving the effectiveness of CXO’s direct reports (the Chief’s peers) as well as leaders throughout the organization. This may involve everything from preparing meeting agendas and planning team off sites to establishing communication patterns and cadence to fostering better interpersonal dynamics.
  • Business effectiveness - Somewhat similar to how a Product Manager approaches iterative product improvements, the Chief is often required to learn the nuances of a specific area of the business to debug a particular system or process. Once they’ve identifying the underlying problems and other sources of friction affecting internal customers, they oversee the implementation of technical or non-technical improvements to get things to a better steady state, before moving on to the next least efficient area of the business and doing the whole thing all over again.

3. Boundaryless engagement

One of the most powerful organizational “hacks” Chiefs of Staff enjoy is that their scope is both boundaryless and organization-wide. For Chiefs this organizational position can manifest itself in the wearing of three “hats”:

  • Float, pinch hitter, or general solver of problems - Going to where the work is regardless of organizational boundaries or corporate hierarchy. This often takes the form of escalation-driven initiative management, but also could involve “important but not urgent” projects that have no clear leader or are otherwise under resourced along with short-lived “special projects” that are important to the CXO.4
  • Connector of dots - Serving as directly responsible individual (DRI) to own “somebody should own this”-type projects, ambiguous and broad-reaching problems that require organization-wide understanding to uncover the true manifestations and possibilities, complex organizational change management, and generally doing what needs to be done without regard for title or stated responsibility.
  • Organizational “air traffic controller” - Helping the CXO prioritize projects; resolving disputes, ambiguity, or otherwise driving consensus; and serving as an honest broker by facilitating tough conversations, all to ensure that organizational planes take off and land on time and without incident, regardless of their origin, destination, or flight path.

4. Portfolio management

In some ways, you can think of a Chief of Staff as a staff or principal program manager, and for many (such as myself), that’s a natural place to transition into the role from. However, as a Chief of Staff, instead of managing one or more well-defined programs, you manage the CXO’s entire portfolio of responsibilities. I’ve written before about the ways program managers bring value to an organization, but there are a few I’d specifically call out as uniquely applicable to Chiefs:

  • Communication, coordination, and facilitation - Communicating decisions and other key updates that may affect others (especially when not immediately obvious), coordinating dependencies and other inter-related efforts across teams (especially when priorities conflict), and facilitating work by ensuring teams have the resources they need (especially unblocking through diplomacy and deconfliction).
  • Reporting up and across - Establishing, operating, and improving the systems that capture, track, and regularly report on work in flight, especially strategic or other cross-functional initiative, to ensure situational awareness at all levels.
  • Identify, analyze, and mitigate risk - The Chief of Staff is the one with their “hands inside of the organizational machine” to identify “squishiness”, bring problem areas to light, drive successful execution, and enable teams to consistently ship with speed and confidence.

5. Strategy, planning, culture, and values

As a Chief of Staff transitions from the more tactical to the more strategic they play an increasing role in not only managing the organization’s day-to-day work, but in shaping what problems the organization solves, how they solve them, and why:

  • Strategy - Shaping the organization’s vision, 3–5-or-10-year plans, OKRs, and other far-reaching strategy documents. At the most basic level, that means working with other leaders to establish, document, and communicate planning materials and to drive the execution rhythm for teams to make progress against those strategic goals throughout the cycle.
  • Planning - Helping leaders carry out the CXO’s vision and strategic intent at all levels. You can think of this as where policy and politics come together. Once they are defined, the Chief of Staff is responsible for communicating the organization’s plans by distilling and cascading those core strategic tenants to both internal and external stakeholders where they can eventually be realized.
  • Culture and values - Establishing, shaping, debugging, and socializing, organizational culture, values, taste, and behavioral expectations. These are the underlying assumptions that an organization’s members fall back on as they resolve ambiguity in pursuit of the organization’s mission. Explicitly and implicitly, Chiefs should set the tone for how the organization prefers to interact, resolve disputes, execute, provide feedback, and solve problems among countless other often invisible decisions that over time can make or break an organization’s success.

6. Advisor and confidant

As a healthy, trust-based relationship develops between Chief of Staff and CXO, a more senior Chief begins to serve as a as strategic advisor and counsel to the CXO by acting as a sounding board as well as second set of eyes, ears, and hands. Specifically:

  • Ear to the ground - The Chief can always be relied on to understand the on-the-ground pulse of the organization in a way the CXO will never be able to by establishing a “you can talk to me” reputation that invites honest dialog. This often takes the form of maintaining ongoing relationships that create the space for frequent feedback, holding regular 1:1s throughout the organization, and elevating questions that otherwise might not be asked of the CXO or the leadership team.5 The insights from these conversations often give rise to initiatives the Chief oversees to improve the “quality of life” for people in the organization and those they work with.
  • Deep understanding - The Chief uses cross-functional knowledge to “scrub in” and deeply understand issues, trends, and perspectives that the CXO may not otherwise have the time to explore in depth. This requires a Chief that thrives in navigating ambiguity through curiosity and research and one that delivers data-driven, concise, and ultimately persuasive recommendations that bring clarity and direction to drive execution. This is not too dissimilar from the role an architect or principal engineer might play within engineering, but for business decisions of the same level of complexity, breadth, and impact.6
  • Proxy - A more senior Chief is distinct in that a core responsibility is to serve as implicit or explicit deputy CXO, to attend meetings on behalf of the CXO and speak as their representative. This is so common, in fact, that it’s often prudent to clarify when you are speaking on your own behalf and when you are acting as the CXO’s stand in. This is one of the many ways the Chief becomes a force multiplier for the CXO, allowing them to be in multiple places at once, at least via proxy. With time, strong Chiefs should also feel comfortable making difficult decisions to advance the business, even in the CXO’s absence.

7. Relationship and brand management

An exceptional Chief of Staff is responsible for managing the relationships and brands of the organization the Chief supports, and by extension both the CXO and the Chief themselves, to ensure the ongoing success of all three. It’s the most difficult aspect of the role to define, and begins to approach “good leadership” generally, but I’d summarize this aspect of the role as:

  • Further a “get stuff done” reputation - In everything they touch, the Chief should embody transparency, predictability, consistency, clarity, thoughtfulness, and sober execution in such a way that the Chief, the CXO, and their organization are all seen as critical partners that increase the likelihood of an initiative’s success through their involvement. Beyond one’s ongoing track record of drama-free ships and demonstrating that they’ve put the time in to deeply understand a particular problem by showing their work, I find one of the most effective ways to do this is to actively manage expectations between the principal, their peers, and the broader universe of stakeholders with the goal of avoiding “surprises” by creating senses of agency and involvement early on and at regular intervals.
  • Lead through persuasion and influence - A Chief enjoys some fiat authority by virtue of their position within the organization, but using it should almost always be seen as a failure to inspire or persuade. Instead, Chiefs should regularly be establishing and growing relationships at each touch point, both on their own behalf, and on behalf of their CXO. This sets the Chief in a position to “know whom to ask” when situations arise, along with enjoying the necessary groundwork to ensure conversations start off on the right foot. Whether it’s the Chief acting directly to solve a problem or facilitating a “high profile” meeting on behalf of others, leading through persuasion expands the Chief and CXO’s sphere of influence well beyond their own organization, allowing them to have an even greater overall impact.
  • Be a thoughtful and kind human leader - All throughout GitHub lore we have phrases like “when in doubt, be classy”, which I didn’t fully understand the implications of when I was first introduced to the phrase, but it applies even more so to a Chief of Staff than it does any role I’ve held in the past. For me, a critical aspect of being an exceptional Chief is about seeking to connect with those you work with as humans, not as means to an ends. It’s about practicing honesty, integrity, decency, fairness, and authenticity in everything you do. Working to support and raise up others, rather than climbing over them to accomplish near-term goals. It’s about approaching software development as a team sport, and being willing to be the leader the team needs when necessary, even if uncomfortable, inconvenient, or not in your immediate self interest.

Conclusion

As I first began settling in, I struggled to get a sense of what a Chief of Staff’s typical day looked like (spoiler: there isn’t one!) or what skills I should be focusing on day-to-day to maximize the value I brought to a principal or executive and to my team. Here’s the list I wish I had as I was first stepping into the role.7 I hope it helps others as they step into similar roles (as well as those they work with) to better understand the role the Chief of Staff plays in improving an organization’s strategy and tactics, health and maturity, and ultimately its overall likelihood of success.

  1. Yes, technically Josh was a deputy Chief of Staff. I also technically had a few arms-length interactions with non-fictional congressional and agency Chiefs of Staff from my time in government, but even then, the focus of the role differs from that of the private sector. 

  2. As in “Chief X Officer”, the corporate executive that the Chief of Staff reports to. This could be a Chief Security Officer, Chief Product Officer, Chief Executive Officer, Senior Vice President of X, etc. 

  3. I define meta-work as the work necessary to unblock shipping. It’s organizational yak shaving, if you’re familiar with the more common engineering term. 

  4. The [“Kinds of projects Chief of Staff Team] to the CEO works on” section of GitLab’s handbook, does a really great job of enumerating this particular aspect of the Chief of Staff’s role. 

  5. Earlier in my career, I’d explicitly avoid gossip and other water cooler talk. As a Program Manager and now as a Chief of Staff, I see it is not only acceptable, but a requirement of the job to be able to hear the otherwise unstated. 

  6. As a former peer and I used to joke of these types of problems, they’re the type that are often best represented by 2x2 matrices or other frameworks one might expect to be taught in business school. 

  7. There are a number of great “What a Chief of Staff does” resources that I read as I was first stepping into the role. Chief Of Staff: The Strategic Partner Who Will Revolutionize Your Organization is a great book if you only read one thing, as is The Gatekeepers: How the White House Chiefs of Staff Define Every Presidency if you’re into history. Beyond books, I’ve Logged 10,000 Hours as a Chief of Staff in a Large Tech Company; Here’s My POV on the Role and The Role of a Corporate Chief of Staff are also great blog posts that informed my early thinking around the role. 

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benbalter

Ben Balter is Chief of Staff for Security and Engineering at GitHub, the world’s largest software development platform. Previously, as a Staff Technical Program manager for Enterprise and Compliance, Ben managed GitHub’s on-premises and SaaS enterprise offerings, and as the Senior Product Manager overseeing the platform’s Trust and Safety efforts, Ben shipped more than 500 features in support of community management, privacy, compliance, content moderation, product security, platform health, and open source workflows to ensure the GitHub community and platform remained safe, secure, and welcoming for all software developers. Before joining GitHub’s Product team, Ben served as GitHub’s Government Evangelist, leading the efforts to encourage more than 2,000 government organizations across 75 countries to adopt open source philosophies for code, data, and policy development. More about the author →

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