The First 90 Days as a Chief of Staff

Rob Dickins
9 min readMar 21, 2019


The Chief of Staff (CoS) role continues to gain prominence in the business world. It wasn’t that long ago that people tasked with performing aspects of a CoS rarely used the title. Today, a search for “Chief of Staff” on LinkedIn returns thousands of results and hiring for new roles is consistently healthy.

As someone who has been in such a role for over seven years, I am passionate about cultivating and contributing to a community of people who see value in the role and have clarity on what it can entail. In my first post on the subject, I offered three potential orientations for a CoS role; each orientation is defined by the primary entity the CoS supports:

  • the principal (the person to whom the CoS reports),
  • the leadership team (of which the CoS is a part), or
  • the organization (over which the leadership team presides).

In this post, I offer thinking on how one might approach the first 90 days of a new CoS role. I believe getting started on the right foot is critical to building a foundation for an impactful tour of duty, particularly given the fact that many who operate alongside a CoS may not know exactly what the role is all about.

As background, I have personally been through four “onboarding periods” in a CoS position — one in Sales, two in Product and one for the CEO. Additionally, I’ve had numerous conversations with Chiefs of Staff and hiring principals within my company (Autodesk) and externally. I’ve attempted to distill my learnings from those experiences and conversations into the summary below so that others have access to it and can build upon it.

Designing the 90 Day Approach

While the exact nature of the onboarding approach may vary somewhat depending on the primary orientation of the role and the person in it, I believe there are some core pillars that are valid and impactful regardless of the orientation. I have used these pillars in my own onboarding to new roles, even as I have gained more experience with the motions of the role over time. The three pillars are: (1) Establish Role Clarity, (2) Strengthen Leadership Team Interactions, and (3) Develop Personal Capability & Capacity.

Establish Role Clarity

Despite the increasing prevalence of the CoS role, there remains some ambiguity on the duties of the position, and perceptions can vary widely on the scope of the role. In some ways, this is because the CoS role is not inherently standard — by design. It can and should be tuned for the specifics of the situation, the individual in the role and needs of the stakeholders. However, it’s precisely in response to this intentional variability that a new CoS must set a time-bound period in the early stages of onboarding to establish role clarity.

Here are some steps to consider when approaching this task:

Gather Data from Stakeholders

The first step is to gather data from key stakeholders. Stakeholders will include the hiring principal, peers on the leadership team and other individuals with whom the CoS will collaborate. I often find that building a stakeholder map early in the process is one way to ensure the identification of a broad and complete list of stakeholders. During the interviews I probe for specific pain points the stakeholders feel and observe today, or what needs stakeholders have which the CoS might help address. Some of this information is obtainable through the written job requisition or the pre-hire interviews, but it helps to dig deeper once one is formally in the role. In addition to catalyzing relationship-building with key people, the interviews offer a great opportunity to uncover emotions and further details from individual experiences.

Distill the Key Themes

The next step is to make sense of the information obtained in the exercise above. Think of it as synthesizing 50+ individual data points surfaced from the interviews. The objective here is to identify the patterns or themes in the data so that the primary focus areas of the CoS role can be established. I have found affinity diagramming, often with a colleague or two, to be a useful and efficient way to progress through this step.

Document in the Form of a Visual Artifact

It’s common and quite natural to perform some version of the above steps when stepping into any new role — and skip what follows. However, for the CoS role, which has historically carried more ambiguity than many other roles, the documentation step is critical to establishing role clarity and ultimately to successful execution. To maximize the value of the documentation step, this task must go beyond simply recording the information for personal reference. The real value comes from investing energy into creating a highly refined, one-page artifact that clearly communicates the intent of the role to stakeholders. It’s important to note that the information in the artifact need not be exhaustive; the objective is not to be comprehensive, but rather to define the center of gravity for the role. It should show everyone what success looks like for the role and help to align stakeholders on 3–5 key priorities for the CoS.

Communicate, Validate and Iterate

Once defined and documented, the information in the artifact becomes a conversation piece between the CoS and key stakeholders. Within the first 90 days of being in a new role, the CoS should share it with at least three key constituencies:

  • the principal, to validate the focus areas and clarify what the CoS is accountable for;
  • the leadership team, so that the leadership team understands what the CoS will focus on and, equally important, what he or she will not focus on; and
  • other key stakeholders in the organization with whom the CoS must collaborate.

The more frequently the CoS communicates and explains the focus areas of the role, the easier it is to describe it to others, with or without the artifact in hand. This process develops the muscle memory for answering the question “so what do you actually do as a Chief of Staff?”

Strengthen Leadership Team Interactions

In every CoS role that I have had, improving the leadership team’s “meeting model” has been one of the key focus areas resulting from a process like the one above. In many cases, addressing it is the primary, most concrete reason for funding the CoS role on the leadership team in the first place. Why? High performing teams know that a robust and efficient meeting model allows the team to inspect the right topics, make high-quality decisions and move the organization forward. A strong meetings model is powerful not just for the leadership team, but for the betterment of the entire organization. The opposite is also true — a poor meeting model at the leadership level can be disastrous for an organization. For these reasons, I promote it here as something to prioritize very early on in a tour of duty.

Here are some steps to consider when starting to tackle this challenge:

Pick or Design a Model

The first step involves picking a model that might work for the team. There is no one model everyone should use; the right model is the one that meets the needs and constraints of the team. I have found the model put forth by Patrick Lencioni to be a good foundation. We have often tailored it to our needs, but the core structure works pretty well.

Document the Model

With an initial design in mind, it’s again important to document the design in the form of a simple, shareable artifact. The artifact should include a range of important details:

  • The types of recurring interactions (e.g., a weekly tactical meeting, a monthly strategic meeting, a quarterly offsite, etc.);
  • The format (in-person or video conference) and the duration of each type of interaction;
  • The expectations for attendance (for example, maybe it’s acceptable for leaders to miss a weekly for a customer meeting, but everyone must attend the quarterly offsite);
  • The target focal length for each type of meeting (for example, the weekly might have topics with a focal length of 0–3 months, whereas the quarterly offsite might have a multi-year focal length); and
  • The focus topics associated with each meeting (or what will guide agenda setting).

By defining this information in a shareable artifact, the leadership team can align on the intent of the model, absent of the calendar. This “as-designed” view can then be given to the person who does the challenging job of scheduling (such as an Executive Assistant). Using a practical mindset, that person doesn’t have to deliver a perfect implementation of the design, but rather the spirit of what we’re trying to do in the face of the many realities of the leadership calendar.

Implement the Model with Some Discipline

Once the model is defined and the recurring interactions are scheduled in the calendar, the CoS is the one who must apply the model with some discipline. This includes designing agendas and managing discussions such that they mirror the intent of the model. Importantly, the CoS must strike a balance between an orthodox implementation of the model and unconstrained flexibility…..between staying within some guardrails and adapting to the natural flow of conversation. Finding this balance takes practice, but it is a critical skill for a CoS.

Determine Priority Development Areas

With role clarity established, and with some early momentum from a higher performing interaction model, the CoS should also reflect on where and how to develop increased capability and capacity over the coming months. Development areas will naturally vary by the role and the person in it, but there is a common set of development opportunities that would benefit many Chiefs of Staff:

  • Personal Productivity. Every CoS must be hyper-organized and hyper-efficient. A new CoS should determine the key digital tools that will enable success and become an expert in them. Additionally, a reflection on recurring workflows, and how to make those recurring workflows more efficient, will pay dividends. This is a useful and easy discussion topic with other Chiefs of Staff in one’s personal network.
  • Knowledge. Depending on the key focus areas of the role, the CoS may be tasked with a range of new responsibilities including strategy development, organizational goal setting, organizational design or other aspects of transformation. The CoS should design a relevant learning path and commit to advancing against it.
  • Facilitation Methods. A good CoS is a master at facilitating dialogue among the leadership team. But being a great facilitator rarely just happens — it requires effort and practice. I have found two things to be particularly helpful in the development of my facilitation practice: (1) studying human psychology, cognitive bias and decision-making, and (2) mastering the use of Human Centered Design tools to structure the conversations and engage all participants in meaningful ways. By combining these domains together, I have been able to advance my facilitation practice over time and deliver higher quality outcomes from our leadership team interactions.

In addition to personal capability development, the CoS should consider how to maximize the ability to get things done with the resources available. With occasional exceptions, many CoS roles do not have direct staff or only have a few people on staff. The CoS must consequently examine the key focus areas and determine how and where additional resources might be brought to bear. Consider these three potential angles of attack appropriate to a CoS role:

  • Direct Staff. Determine if adding a handful of direct staff makes sense. The types of hires that commonly show up on a CoS team include project managers, program managers, and communications professionals (to support internal organizational communication and/or external communications for the principal).
  • Borrowed Resources. As a member of the leadership team and someone close to the principal, the CoS often has access to functional resources throughout the organization. Those on the leadership team and others throughout the organization are often happy to contribute team time, as the work of the CoS is focused directly on moving the broader organization forward.
  • Third Parties. While the CoS may not have a large direct staff, access to funding is often a possibility where the work is in line with the leadership agenda. This can be a helpful track to provide momentum to key initiatives when internal resources are strained.

Making an impact early in a tour of duty is important for any new CoS. It’s even more important when there aren’t many existing examples of other Chiefs of Staff in a given organization. I hope the thinking above provides value to those embarking on such an adventure and contributes in some small way towards greater success in the role.



Rob Dickins

Chief of Staff to the CEO @ Autodesk; passionate advocate, instructor, and facilitator of Human Centered Design