The Ultimate Chief of Staff Playbook: From Shadow Operator to Strategic Leader

A Chief of Staff (CoS) is broadly understood as the right-hand person and “force-multiplier” to a leader, often a CEO or other C-suite executive. In practice, this means the CoS works closely with the leader to execute strategic priorities, manage the leader’s office, and align the organization. The role originated in government and military contexts (e.g. White House Chiefs of Staff have long been key Presidential aides), but it has become increasingly common in tech companies and startups in recent years.

At its core, the CoS role is about amplifying the effectiveness of the principal (the executive the CoS supports). Instead of having their own separate team or agenda, a CoS works across the organization on behalf of the leader. Commonly cited responsibilities of a CoS include:

• Administrative executor: “Make the trains run on time” by handling day-to-day operations, meetings, and ensuring decisions are implemented.

• Gatekeeper: Protect the leader’s time and focus by triaging communications, meeting requests, and sometimes saying “no” on the leader’s behalf.

• Counselor/Advisor: Serve as a confidant and sounding board to the leader – someone who can offer honest feedback, diverse perspectives, and speak truth to power in private.

• Implementer/Project Driver: Drive key initiatives and cross-functional projects to completion, often those that fall between departmental silos or below the leader’s direct focus.

• Proxy/Representative: Step in for the executive when needed – communicating decisions, representing the leader in meetings, and ensuring the leader’s vision and standards are upheld.

These five aspects (as identified by McKinsey research) illustrate the multiple hats a CoS may wear. Other experts have described similar archetypes – for example, author Richard Hytner defines CoS roles like Lodestone (relieving the boss’s workload), Educator (coach and independent perspective), Anchor (steady confidant), and Deliverer (driver of results). Regardless of the terminology, the CoS role is multi-faceted by design. It combines elements of strategic planning, operational management, communications, and trusted advisory into one high-impact position.

Example: Before she became Facebook’s COO, Sheryl Sandberg served as Chief of Staff to U.S. Treasury Secretary Larry Summers – illustrating how the CoS role can provide a wide-lens leadership experience. In that government role, Sandberg controlled access to the Secretary, coordinated policy initiatives, and learned to “manage up” – experiences that later informed her success in tech leadership.

Typical Responsibilities and Key Functions

While each CoS position is unique, there are some key functions and deliverables commonly expected from Chiefs of Staff in a business setting:

• Managing Executive Priorities: A CoS often oversees the executive’s prioritization and schedule. This can include running calendar audits, preparing the leader’s meeting briefs, and filtering incoming requests. By acting as a gatekeeper, the CoS ensures the leader is focused on the most strategic issues. They might also track and remind the executive of key action items and follow-ups to keep priorities on track.

• Internal Communication & Alignment: Many Chiefs of Staff take charge of internal communications and meeting cadence. For example, a CoS may prepare agendas and run leadership team meetings, document decisions, assign follow-ups, and hold teams accountable. They frequently manage All-Hands meetings or company newsletters, draft the CEO’s updates to staff, and create frameworks for decision-making – all to keep the organization aligned and informed.

• Project and Program Management: Chiefs of Staff commonly spearhead special projects that don’t neatly fall into one department. They are the consummate cross-functional project managers, whether it’s leading a strategic planning process, driving an OKR (Objectives & Key Results) program, or exploring a new business opportunity. One CoS described her role as “playing chess, not checkers” – always thinking a few moves ahead across the business.

• Strategic Advisory: As one of the few people with a company-wide purview, a CoS often serves as a strategy advisor to the CEO. They might synthesize data and insights for the CEO (e.g. analyzing metrics dashboards or business reviews), evaluate proposals before they reach the CEO, and provide input on high-level strategy discussions. This advisory role requires a CoS to develop strong trust with the leader and to be able to give honest feedback behind closed doors.

• Operational and Administrative Support: Especially in earlier-stage companies, a CoS may handle many operational tasks to fill in organizational gaps. This could mean anything from helping HR with recruiting top talent, to drafting policy documents, to liaising with Finance on budgeting. In larger orgs, there might be more administrative support (executive assistants, etc.), but the CoS still ensures the leader’s office runs smoothly – often designing and supervising the processes for decision approvals, information flow, and execution follow-up.

It’s important to note that a Chief of Staff is not merely a glorified executive assistant (EA). Unlike an EA, who typically focuses on logistical support, the CoS is a strategic operator and surrogate decision-maker. As former LinkedIn CEO Jeff Weiner’s CoS put it, “a CoS helps leaders work on the organization rather than just in it”. The CoS may work closely with the leader’s Executive Assistant (in fact, a great CoS-EA partnership can dramatically increase a CEO’s effectiveness), but the CoS role goes beyond scheduling and admin; it encompasses high-level problem solving and leadership support.