The Chief of Staff Guide — Part 1: Intro

May 12th, 2018

This is the first article in a four-part series about the Chief of Staff role. In subsequent articles, I explore how to shape the role, how to avoid common pitfalls, and how it advances your professional development.


Over the past 5 years, I’ve received many calls for advice about Chief of Staff roles.


I’ve formulated reflections on how to make the most of the role through conversations with individuals contemplating the role for the first time, CEOs considering hiring a Chief of Staff, and current Chiefs of Staff looking for guidance. This guide is intended to help any of these constituents, though for linguistic simplicity I’ve written this to current and prospective Chiefs of Staff.


Serving as Chief of Staff can be a career-changing experience. But it’s not for everyone. It’s a difficult role, and no two Chiefs of Staff have the same journey. It’s highly dependent on the fit between the Chief of Staff, the company, and the CEO. You will gain broad company exposure and C-level visibility far above your pay grade, but risk operating as a glorified assistant if the role is poorly designed. You will have internal air cover to help the organization achieve its most ambitious goals, but the work of developing and maintaining the trust to do that borders on Sisyphean. It’s a high beta role — higher risk, higher reward. The role is what you make it, and this guide is designed to help you make it successful.


Drawing on my experience, as well as the experiences of other Chiefs of Staff, I will address three major topics:

  1. How to shape the role
  2. How to avoid common pitfalls
  3. How to manage your career path


What is a Chief of Staff?

The Chief of Staff title is attached to a range of roles spanning from primarily administrative to highly strategic. Some Chiefs of Staff are executive assistants with aide-de-camp responsibilities, while others operate as senior executives with broad oversight. The liberal use of this level-less title causes confusion for those considering the role.


I will focus on Chief of Staff roles that are primarily strategic — not roles that use the title to reflect “assistant-to” responsibilities (e.g., an executive assistant who attends meetings and ensures follow-ups are completed). As with any role, the Chief of Staff needs to enable his or her boss — typically the CEO — to be successful. However, the Chief of Staff has additional conflicting customers, including the executive team and the company as a whole. As I will explore, the Chief of Staff will need to dynamically interpret this broad mandate in the context of his or her own organization.


While I will confine my discussion of the Chief of Staff role to those serving as a strategic (vs. administrative) partner to a CEO or other senior executive, the role still varies by two principal factors: the stage of the company and the independence of the role.



Chiefs of Staff are often hired into rapidly growing organizations. During periods of intense growth, the fundamental structure of an organization shifts, and almost everything that worked in the prior structure breaks. Organizational structures need to change, decision-making authority becomes unclear, scope and turf issues arise, new people are needed at multiple levels, and basic processes across the organization — from financial planning to code releases — need to be created and destroyed. As these fundamental structures evolve, a Chief of Staff can help manage growing pains by designing and running a new “operating system” for the organization. Chiefs of Staff also exist in more established and slower-growth organizations, but I don’t know enough to represent that end of the spectrum.



The second factor that defines the role is the level of independence the Chief of Staff enjoys. At one extreme is the bodyman model, where the Chief of Staff travels with the CEO, attends most of the CEO’s meetings, prepares briefs, takes notes, and acts on follow-up items. This conjoined model lends itself to a more administrative focus. At the other end of the spectrum is the solo model in which the CEO and Chief of Staff primarily function independently. They might spend a few hours together each week, but they won’t travel or attend many meetings together, and the Chief of Staff primarily sets his or her own agenda. There are many gradations between these two extremes.

This series will primarily focus on the strategically oriented, primarily independent Chief of Staff role at high-growth companies, which was my experience and the experience of many of my ex-Chief of Staff colleagues. In this capacity, you might expect to serve in the Chief of Staff role for 2-3 years before moving on to other responsibilities — more on this in the Career Path article.


In the next article, I describe how the Chief of Staff creates value and the primary duties that reflect this value. I also provide guidance on how to shape the role to maximize impact across the Chief of Staff’s broad range of duties.