Companies big and small are increasingly hiring “Chiefs of Staff” to support their CEO, COO, CTO, or other key executives. Although the the Chief of Staff role differs widely, at its core, having a Chief of Staff allows the executive to scale, and it gives them back their most important resource: time.
I worked for Tony Hsieh, CEO of Zappos, for 4 years, and was his Chief of Staff for 2 of those. During that time, I had the benefit of meeting and learning from many other Chiefs of Staff. I want to share those insights here.
In this 5-part series, I’ll cover:
Part 1: The Role of a Corporate Chief of Staff
Part 2: How to Become a Chief of Staff
Part 3: How to Find and Hire a Chief of Staff
Part 4: Chief of Staff — The First 90 Days
Part 5: Chief of Staff Best Practices
This series does not cover the more traditional political or military Chief of Staff description, which was where the term originated from. For more on that, you can read about The White House Chief of Staff and The Chief of Staff of the United States Army.
I will use the phrase “Chief of Staff” or “CoS” when discussing the role, but it can also be represented through any of the following descriptions:
- Civilian Chief of Staff
- Chief of Staff to the CEO
- Corporate Chief of Staff
- Business Chief of Staff
- Advisor to the CEO
- Office of the CEO
- Special Assistant to the CEO
The CoS typically operates in highly ambiguous environments. Al Chase, an executive recruiter who specializes in CoS placements, writes “the CoS operates at a tactical, strategic and operational level, often handling the oversight of projects that do not neatly fit within the organizational chart or [that] fall between departments or leaders areas of responsibility”. The CoS’s responsibilities might overlap with those of a specific functional lead, such as the COO or Director of HR, but they are much more nimble in helping meet timely business needs or gaps.
Below is a list of the major types, or functional areas, of CoS responsibilities. The CoS role varies significantly depending on the size of the company, the executive who is being supported, and the background of the individual Chief of Staff. The CoS role might comprise just one of these functional areas, it might combine multiple areas, or it might even evolve as business needs change.
- Scheduling high priority meetings
- Coordinating executive calendars
- Planning and executing senior management retreats, all-hands meetings, and company offsites
- Taking meeting notes
- Tracking meeting follow-ups
- Maintaining a Rolodex of important contact information
Unlike with an Executive Assistant (EA), the CoS role is not a Monday-to-Friday, 9-to-5 role. The CoS is typically available evenings and weekends.
- Tracking high priority initiatives for the executive and identifying any obstacles
- Communicating initiative status to the executive, pulling in other executives or team members as necessary
- Connecting teams that are working on similar initiatives
- Pulling together and managing project teams that require input from multiple areas within the company
The CoS often doesn’t manage any headcount of their own. While their influence is derived from their executive, they still need to obtain information from other business unit leads who they don’t have any formal authority over. This requires significant relationship building.
- Running the annual budget cycle process (for example, helping department heads prepare their budget materials for presentation to the CEO)
- Project managing board meeting preparation and creation of board meeting materials
- Running quarterly business reviews
- Creating and updating monthly dashboards to track changes in key metrics
- Analyzing investment opportunities
This is one of the most common functions of a CoS — helping with the budget cycle, business reviews, or with board meeting preparation. It integrates both administrative functions (such as scheduling meetings and compiling presentations) and highly strategic functions (such as analyzing specific budget requests and determining what to cut).
- Identifying and taking on ad hoc strategic projects (for example, executing key initiatives or closing any operational gaps)
- Defining and researching new ideas and business opportunities
- Building out a new business unit
- Providing decision support through data gathering, information analyzing, and presenting considerations to relevant stakeholders
- Designing and executing a corporate communication strategy
- Drafting speeches and presentations
- Vetting speaking opportunities and interview requests
- Updating recruiting processes
- Overseeing diversity and culture initiatives
- Reviewing organizational structure, identifying any gaps, and filling them
- Aligning internal processes
- Serving as a trusted advisor and confidant to the executive
- Attending meetings in place of the executive
- Making decisions in place of the executive
- Managing critical relationships on behalf of the executive
- Assessing all inquiries directed to the executive and determining the proper course of action
- Determining which meetings take priority
- Vetting requests for time and routing requests to other departments as appropriate
Gatekeeping is another common and critical function of the CoS. The executive is constantly getting requests for their time, money, advice, or other resources, and they need someone who can vet and respond to these requests appropriately. This requires a high degree of understanding and trust between the COS and executive.
- Deciding which charitable initiatives to contribute to
- Traveling with the executive to conferences or meetings
- Acting as a “body man” at conferences (read about Obama’s body man, Reggie Love, here)
The Chief of Staff role is much more than the simple aggregation of the individual responsibilities listed above. The most successful CoS’s dynamically integrate these responsibilities and can track the flow of a relationship, project, or initiative from end-to-end.
An example of this might be a CoS attending a conference where his executive is giving the keynote speech. The CoS works with the executive on their speech, gathering key data points and graphics that the executive wants to present. They coordinate with the conference organizers both in advance of the conference and on the day-of to make sure everything is properly set up. They also coordinate with the executive’s personal assistant to make sure travel goes smoothly, and they have a backup copy of the car and hotel reservations along with all relevant contact information.
The CoS has arranged for the executive to hold a few key meetings at the conference and has prepared a pre-read brief on each meeting for the executive. The CoS sits in on the meetings, takes notes, and tracks any relevant follow-ups. The executive is running late to one meeting so the CoS begins it, and by the time the executive arrives, the CoS has built a good relationship with the other meeting participants and is able to quickly get everyone to agreement.
Later that afternoon, the executive gives her keynote speech. After the executive finishes her speech, the CoS acts as a “body man” and helps manage the flow of people who have approached the executive, rotating people through, and trading contact information with everyone so they can follow up. At the end of the evening, the CoS and the executive recap how the day went and align on priorities for the rest of the trip.
When I worked for Tony, I was on a Chief of Staff team that loosely encompassed a combination of his Executive Assistant, his Personal Assistant, senior advisors, junior support personnel, and even another Chief of Staff who was the CoS at Zappos. Given Tony also founded Downtown Project (a revitalization effort for Downtown Las Vegas where he contributed $350 million of his personal wealth), has invested in 100+ tech companies and small businesses, and sits on several boards including at JetSuite, his full support team doesn’t just include Zappos employees but also encompasses individuals at Downtown Project and elsewhere.
Many other high profile tech executives have similar CoS support teams that help them more effectively manage their incredible breadth of professional and personal commitments:
- Ryan Metcalf, Max Levchin’s former CoS, writes about supporting Max across “four companies, two public boards, five private boards, fourteen direct reports and [his] family front office” through Max’s roles at Affirm, HVF, SciFi VC, Glow, Yelp, Yahoo, Evernote, and more
- Ben Casnocha, Reid Hoffman’s former CoS, writes a great piece about what he learned while working with Reid at LinkedIn
- Brian Screnar, Nathan Myhrvold’s CoS, supports Nathan in managing his billion-dollar investment and tech incubation fund, as well as on projects as diverse as: next-generation nuclear fission power, dinosaur growth rates, and modernist cooking
- Michael Kratsios, Peter Thiel’s former CoS, supported him across Thiel Capital, Founders Fund, and Mithril Capital before being tapped as the White House Deputy CTO
- Finally, Elon Musk has a longtime CoS — Sam Teller. As a recent Slate article on Elon Musk reveals, “if you’re looking for the person who most often serves as Musk’s right hand, you won’t find them in the C-Suite, or even anywhere on Bloomberg’s extensively researched org chart, one former Tesla employee told Slate. It’s Sam Teller, director of the office of the CEO for Tesla and SpaceX, who functions essentially as Musk’s chief of staff.” And let’s not forget the Boring Company, which Sam is also a spokesperson for.
At Amazon, the parent company of Zappos, the CoS role is formally known as a “Technical Advisor” and informally known as a “shadow”. Amazon CEO Jeff Bezos has had over 10 shadows, including: Jeffrey Helbling, Maria Renz, Andy Jassy, Danny Shader, Matt Williams, Stig Leschly, Amit Agarwal, Greg Hart, Dilip Kumar, Ian Freed, and Jay Marine. Recode reports that “historically, shadows have gone on to run some of the company’s most crucial initiatives after their typical two-year stint is up”. You can read more about the Amazon shadow role here and here.
In the next part of this series, we’ll explore what a typical CoS background looks like (spoiler alert: there isn’t one).
CNBC overview of the CoS role and interviews with several CoS’s — read it here
Washington Post article covering the Silicon Valley CoS group, which includes the CoS’s of the CEO’s of LinkedIn, Salesforce, Hewlett-Packard, Yahoo, Uber, Lyft, Dropbox, and DocuSign — read it here
New York Times article on the evolution of the CoS role and the CoS Tech Network — read it here