I’ve Logged 10,000 Hours as a Chief of Staff in a Large Tech Company; Here’s My POV on the Role

I have held the role of Chief of Staff for over 6 years, under 3 different SVP’s (one of whom served as Chief Product Officer and Co-CEO of the company), and within 2 functional organizations (Sales and Product). Through this experience, I’ve advised dozens of people — leaders looking to hire a Chief of Staff, people newly in the role, and those aspiring to be in such a role. These people have come to me looking for insights regarding what I have learned and how I see the role. I’m writing this article to refine and codify what I share in those conversations; my hope in doing so is that a broader community of people can have access to the thinking and build upon it.

First Things First — A Little Context

The traditional image that jumps to mind when one hears the words “Chief of Staff” is the White House, and specifically the White House Chief of Staff. That role has existed for decades, and there has been plenty written on the subject (perhaps more than normal in recent months, but I’ll spare this from turning into a political post).

The Chief of Staff (CoS) role has emerged on the business scene more recently….in the last 5–10 years by my estimation. One theory on why it has emerged is grounded in the increased pace of external change, which in turn has forced more and more companies to transform their organizations and manage new degrees of complexity. Since the CoS role is generally chartered to help bring order to things, the rising trend makes sense. Today, you can search LinkedIn and easily find people currently in such roles or open requisitions looking to be filled.

The point of view I share below is informed by my experience at Autodesk, a large, publicly-traded software company focused on building tools for people who make things.

The Three Orientations for a Chief of Staff Role

In my experience, I’ve come to believe there are three potential orientations which a CoS might have in terms of focus and impact. All three orientations involve the same reporting structure, but how the CoS considers the role — and prioritizes the type of work to be done — varies. I believe grounding the conversation in these three orientations helps create a useful framework for subsequent explorations about the role.

Orientation #1 — The Principal

The first orientation focuses on the Principal — the leader to whom the CoS reports. The Principal could be a CEO, the head of a business unit, or the leader of a function. In this orientation, the goal of the CoS is to do things that enable the Principal to operate at a higher level of performance.

What might a CoS do in this orientation? It’s often a mix of things, including serving as

• A strategic advisor and confidant (a highly trusted person with whom to discuss and pressure-test ideas);
• An extra set of hands (to help with presentation development or ghost-writing communications);
• A proxy for the Principal (for people who can’t get time with the Principal); and/or
• An organizer (to help manage a picture of the priorities, projects, decisions, and actions that should be in the brain space of the Principal).

Because of this focus on the Principal as an individual, the duties of the role in this orientation can sometimes be interpreted as a “super assistant”. This style of charter was described through another detailed and well-crafted post, written from the perspective of a CEO of a startup. It’s definitely worth a read, you can find it here.

Orientation #2 — The Leadership Team

This second orientation goes beyond the Principal to include the leadership team over which the Principal presides. Analogous to the first orientation, the goal of the CoS in this case is to do things that enable the leadership team to operate at a higher level of performance.

This orientation demands a broader and perhaps more sophisticated set of skills than Orientation #1. Areas of work that might fall under this orientation include:

• Formulating and managing the strategic agenda of the leadership team;
• Setting the cadence of leadership team interactions, and running staff meetings;
• Identifying the appropriate inspection topics and mechanisms for leadership staff; and
• Ensuring a strong, candid team dynamic by creating an optimal environment for productive, professional dialogue.

Viewed from outside the leadership team, this role can appear as “the person who develops the staff meeting agenda and takes really good notes”. Viewed from within the leadership team, it’s often much different. Those who see the day-to-day operation of the CoS in this orientation often describe the person as the “glue that keeps us working together as a cohesive and effective team”.

In this orientation, I find it useful to think about five big pillars of work:

1. Interact — How can I help this leadership team work better together?
2. Interface — What are the critical interfaces between this leadership team and other organizations in the company, and how can I help strengthen those interfaces?
3. Plan — How might I design and orchestrate our strategy and planning efforts to get the best results?
4. Measure — How are we inspecting our progress, and how do we hold ourselves accountable for achieving our desired results?
5. Communicate — What are we messaging to the broader organization, at what cadence, and through what mechanisms?

Beyond these pillars, the CoS might be asked to look after certain initiatives or teams directly in this orientation. For example, there might be an emerging capability in the organization, but we’re not yet sure where to put it; placing that team under the Chief of Staff provides a neutral place with some air cover and close proximity to the Principal while it matures and learning can take place. Another example might be short-term, critical projects that span several members of the leadership team or parts of the organization.

Notably, it’s in this orientation that the CoS might begin to build a small team of people who can help…for example, someone who can help with internal/external communications, or a program/project manager who can help lend capacity for bigger projects the CoS might oversee.

Orientation #3 — The Organization

The third and arguably the most impactful orientation for a CoS puts the organization in the center of the frame. In this orientation, the CoS is first considering (and contributing to) strategy. Once strategy and direction are clear, the CoS then seeks the answer to one broad question: “Given what we now aim to do, how might we best set up our organization to accomplish these objectives?”

In this orientation, the CoS is essentially a Chief Operating Officer (COO) in sheep’s clothing. Since it can be awkward to have a bunch of COO’s of business units running around in a big company, the CoS title becomes more appropriate and less dramatic. Nevertheless, the CoS role is every bit as important as a COO one. To illustrate my point, in my current role, the product organization our leadership team looks after includes thousands of employees, in a variety of functional roles (engineers, designers, product managers, etc.), spread over many countries and time zones, with an operating budget approaching that of some Fortune 1000 companies. Viewed in this light, one might legitimately ask how such an organization can function at a high level of performance without a COO-like role.

In this orientation, an effective CoS might study how other COO’s interpret their role at various companies and then model those motions and behaviors. Specific topics and focus areas in this orientation include:

• Organizational design — working with the Principal and organizational development (OD) professionals to design the most effective organizational structure;
• Key business capabilities — prioritizing what the organization needs to be great at, then influencing how orchestrated investments in people, processes, and technology drive the advancement of such capabilities;
• Critical interfaces and dependencies — clarifying and overseeing connection points within the unit and with other organizational functions;
• Governance — defining the critical recurring interactions, inspection mechanisms, and decision rules to ensure strong project execution; and
• Optimization — generally looking for and addressing gaps and inefficiencies across the organization.

In this capacity, the CoS is a principal architect, champion, and curator of the organization’s operating model, just as a COO serves that function for an entire company.

Working With the Orientations

All three of the above orientations can provide value; none are inherently better or more appropriate in all circumstances. As any CoS will tell you, the role is always tailored to the situation and the Principal. It’s for these reasons that it’s important for the Principal and the CoS to engage in an explicit conversation on how they see the role. Being intentional about how the role is set up delivers a shared set of expectations that form the basis of a good and productive relationship.

In my experience, when I begin a new relationship with a Principal, I often move through Orientations 1, 2, and 3, almost like phases. We start with Orientation #1 because we need to learn each other’s style, strengths and weaknesses. There are several things I can do immediately, which the Principal needs, and that provides a good start. After we have a rapport and working dynamic, I click out one concentric circle to the leadership team (Orientation #2) and invest more of my time there. Finally, once we have a pretty solid operating rhythm at the leadership team level, I click out one more concentric circle to think more about the broader organization (Orientation #3)….how we might shape and evolve everything we’re doing to produce better results and enable us to achieve our strategic objectives.

It’s worth noting that even when the primary orientation for the role is Orientation #3, the kind of work required in Orientations #1 and #2 doesn’t really go away. They are still required for Orientation #3 to work, so it’s more an issue of balancing the three orientations.

Establishing a New Chief of Staff Role

If you’re a Principal looking to create a new CoS role, there are some questions you might want to explore to build a good foundation for success:

• What needs do you and/or your leadership team have today? What needs might you envision a little bit down the line? Write up a list of the gaps or weaknesses which having a CoS might solve for.
• Given the list of core needs, is there a preferred orientation for the role, initially and over time?
• Think about which orientation you’re hiring for. The profile of the person that will be successful in Orientation #3 is such that they can likely also deliver on Orientations #1 and #2, but the opposite may not be true.
• Do you see the role as a rotational opportunity or a semi-permanent position? Either approach can work, but you will get different kinds of candidates — and results — depending on how the role is defined.
• Similarly, is it a full-time job, or are you asking a leader with other responsibilities to play the role of CoS in addition to their other role?
• Finally, once you fund the role and fill it with a good candidate, consider helping the new CoS be successful by clearly messaging the person’s role and charter. Viewed from the outside, it’s often a mysterious and ambiguous role…and that’s unnecessary. A certain degree of ambiguity can be useful (so scope for the role isn’t limiting), but there are also some nuts and bolts aspects of the role that can be articulated for broader understanding.

Skills To Look For in a Chief of Staff

You might be a Principal looking to establish the role, a prospective candidate for a role that is posted, or a CoS currently in the role and thinking about how to raise your game. For all of these situations, consider these foundational CoS attributes, regardless of orientation:

• Super Organizer — Because a CoS is often brought in to help bring order to things, the individual needs to be a methodical organizer. This a probably the most well understood attribute of a good CoS.
• Strategic Thinker — The CoS needs to be able to see the big picture of things. A strategic mindset helps align detailed work to the big picture strategy, as well as evaluate what is urgent versus important.
• GSD Reputation — GSD stands for Get [Stuff] Done. The Principal and the leadership team need to know that responsibilities or tasks that fall to the CoS are guaranteed to get done. The CoS should have a reputation for never dropping the ball.
• Trusted Operator — The CoS is often exposed to sensitive or confidential information in the normal course of executing the role. Consequently, the person in that role has to innately appreciate how to manage such information in confidence and with discretion.
• Expert Facilitator—Finally, a day-to-day part of being a CoS requires managing conversations, synthesizing multiple points of view, and aligning on direction…all in an impartial and professional way. In that regard, the individual needs both the temperament and tools to facilitate and land a wide variety of conversations at various levels of the organization. In my own case, I have invested time and energy in becoming an expert at leveraging Human Centered Design (or Design Thinking) methods because I find such tools well-suited to this need.

Since the pace of external change — and the consequent demand for ongoing business transformation — is showing no signs of slowing down, I suspect we will see this role continue to pop up in more places in the coming years. My hope is that the above thinking (1) contributes in some small part to helping the individuals in such roles be more successful, and (2) encourages them to join the dialogue and contribute to the thinking around this important and impactful role.