James Baker, at left, is considered to be the most effective White House Chief of Staff in history, [1] a notable accomplishment given how many otherwise talented people are perceived to have failed in the role. [2]
Most of my clients are CEOs, most of them have executive assistants, and a theme in my practice is helping clients make the best use of this support. [3] But a number of clients are also opting to hire a Chief of Staff, and given how widely the job description can vary, it's useful to clarify expectations for the role and note how it contrasts with (and is similar to) that of an EA.
Overview
While the term "chief of staff" has a long history in the military, referring to the head of an armed force, in a civilian context the model for the role is the White House Chief of Staff in the United States. Beginning with one Tobias Lear who served George Washington, this position was referred to as the Secretary to the President until Harry Truman awarded John Steelman the current title in 1946, and every U.S. president since then has had a Chief of Staff, with the partial exception of Jimmy Carter, who initially opted to leave the role vacant, a decision he would later regret:
One of Carter’s failings as president related to both his personality and how he structured the staff at the White House, and these were interrelated. Carter’s intellectual rigor was one of his major strengths that turned into a major weakness. He believed that he was smarter than anyone else and didn’t need others. As a result, he would bury himself in reading and understanding every detail, while neglecting broader strategic aims. For the first two years of his presidency, Carter operated without a chief of staff, believing it was unnecessary. It was a surprising error for someone who usually understood history well. Even a quick survey of how other presidents had dealt with the management of information and access would have led him to see the necessity of a chief of staff. It took him two years to realize he needed one, but by then he had lost critical momentum. [4]
I see a version of this in my practice: as I've written before, "a CEO who's spending time on tasks that could be delegated...isn't being 'lean and scrappy'--they're stubbornly clinging to an outdated job description and hurting the business as a result." [5] This realization often leads my clients to hire their first EA, to promote a shared EA into a dedicated role, and, increasingly, to hire a Chief of Staff.
Tenure
With EAs I make a distinction between "dedicated assistance" and "professional assistance." [6] The former occurs when the CEO's EA fills the role in a full-time capacity with no other responsibilities (such as office management) and works solely for the CEO rather than supporting multiple executives. For many dedicated EAs the role is not a career path, and after several years they move on to pursue other opportunities or interests that are more aligned with their long-term goals. The latter occurs when an EA does view the role as a career path, and when a CEO and a professional EA develop a strong relationship they often work together for many years.
In this sense the Chief of Staff role is analogous to a dedicated EA: It's rarely a career path, but will mostly likely serve as a stepping stone to a bigger opportunity. A CEO hiring a Chief of Staff should anticipate that the role will turn over as soon as 12 or 18 months, and almost certainly within several years. However, unlike many EAs, almost all Chiefs of Staff are first-timers--they've never held the job before and may not really understand what it entails. Given these factors, it's essential that they get up to speed quickly, which will require a heavy investment of time by the CEO during the onboarding process. But once a CEO has hired their first Chief of Staff, it's common to ask an outgoing Chief of Staff to lead the process of sourcing candidates to replace them, enabling them to assist with onboarding their successor.
Scope
A key to success for both Chiefs of Staff and EAs is recognizing that one of the organization's most valuable resources is the leader's attention [7], and one of the essential functions served by support staff is to safeguard that resource and enable the leader to focus on what's most important by helping them set and maintain priorities, augmenting their capacity, and shielding them from distractions. With a Chief of Staff as well as a dedicated or professional EA, a CEO can expect to steadily increase the scope of their responsibilities over time, although the nature of this trajectory in each role often differs. The primary duties can be categorized as managing access, serving as a proxy, and delegated tasks.
Managing Access: The White House Chief of Staff oversees access to the President and has considerable discretion in setting the daily and weekly agenda. Few of my clients' Chiefs of Staff possess such authority, although I often encourage clients to consider how they might further empower support staff, including EAs, to enable them to be as effective as possible. This can take the form of additional 1:1 time, sharing further information regarding priorities, and ensuring that staff roles are invested with sufficient status (see below). EAs are more likely to provide support with calendaring, but in either case it's essential that staff view this work not as meeting the needs of people who want time with the leader, but, rather, as enabling the leader to focus their attention on their top priorities.
Serving as a Proxy: The starting point here is serving as the CEO's "eyes and ears"--a Chief of Staff may sit in on a meeting in lieu of the CEO without actively participating, while an EA is more likely to sort and prioritize the CEO's Inbox. The next step involves playing a more active role in these settings, which usually entails representing the CEO's explicitly understood point of view on specific topics. Ultimately both roles may be empowered to act independently with the imprimatur of the CEO's authority. Again, it's more common for the Chief of Staff to fulfill these responsibilities in-person, while an EA is more likely to work behind the scenes, e.g. via email.
Delegated Tasks: This can range from various forms of personal support to taking on an interim executive role. Regarding the former, it's critical to clarify in advance the extent to which providing personal support is a part of the job. Some CEOs have their staff play a hybrid role with little distinction between personal and business domains, while others maintain a strict separation (and often employ a personal assistant as a result.) Chiefs of Staff are more likely than EAs to serve in an interim executive capacity, but their ability to do so will be contingent on the status afforded the role within the organization.
Status
I refer to status throughout this post because I believe it's of the utmost importance in enabling support staff to fulfill their duties effectively. One of the most difficult aspects of both the Chief of Staff and the EA role is having to interface with powerful figures who view support staff as gatekeepers preventing them from accessing the leader, or who would prefer to deal directly with the leader rather than their proxy. In most cases these figures occupy a higher-ranking role within the organization or possess other forms of high status. The work of deterring such figures must be done firmly but gracefully, requiring a high degree of emotional intelligence--I've never encountered a top-flight Chief of Staff or EA who lacked this capacity. And such efforts are facilitated when the leaders' support staff themselves enjoy high status.
In some cases this is easier for a Chief of Staff than it is for an EA--the terms "chief" and "assistant" have very different connotations, of course. But while an EA may benefit from a long association with the leader or may be older and more experienced than the otherwise powerful figures they encounter, a Chief of Staff is usually relatively new to the organization and is almost always younger and less experienced than those same figures. In all cases it's incumbent on the leader to pay close attention to the ways they bolster--or undermine--their staff's status.
Compensation can play a role here, but largely through its impact on retention, which is usually less relevant for Chiefs of Staff who are expected to transition relatively soon. (Although note that this is why professional EAs who build a long-term relationship with a leader are often highly compensated.) More significant are the visible forms of status that signal support staff's value to the leader, such as 1:1 time with the leader, participation in certain select events, and the nature and tone of all public communication between the leader and their staff.
So if you're a CEO hiring a Chief of Staff, what can you do to help both parties make the most of the opportunity?
- Build a feedback-rich culture and ensure that your Chief of Staff feels comfortable giving you critical feedback when necessary.
- Understand your work style preferences and be able to convey them with clarity. (This may--or may not--involve a "Manager README" document.)
- And be prepared to invest a lot of time and energy up front--being your Chief of Staff will almost certainly be a tougher job than their previous role, and they'll need your help to get up the learning curve.
Footnotes
[1] For example, see History's Greatest Chief of Staff Just Gave 2 Sentences of Genius Advice to the Newbie (Scott Mautz, Inc., 2017) or From the Fabulous Baker Boys to the Master of Disaster: The White House Chief of Staff in the Reagan and G. H. W. Bush Administrations (David Cohen, Presidential Studies Quarterly, 2002) The title of the latter, drawing on a 1989 movie of the same name, refers to James and Howard Baker (no relation), who served as Chiefs of Staff to Ronald Reagan and are both regarded as being uncommonly effective.
[2] List of White House Chiefs of Staff
[3] Three Stages of Executive Assistance
[4] Jimmy Carter's Fatal Flaw (Mike Purdy, Presidential History, 2018)
[5] Three Stages of Executive Assistance
[6] Ibid.
[7] Growth, Profitability and Return on Attention
For Further Reading
How to Be a Great Chief of Staff in Tech (Eric Nehrlich, 2019)
- Eric shared this with me after I published this post, and I think his first-person perspective is an outstanding companion piece (and even more valuable to aspiring Chiefs of Staff.)
Resources on the Chief of Staff Role in Business (Maïa Cybelle Carpenter, 2018)
Photo by the U.S. Coast Guard Academy.
