Rob Dickins, Vice President & Chief of Staff to the CEO of Autodesk, explores different methods for assessing the value of a chief of staff.


In business, we often assess opportunities through the lens of Return on Investment (ROI). We consider whether we should invest in something based on the potential financial (and sometimes non-financial) return. I work at Autodesk, a world-leader in design and make technology. We build software that serves professionals in fields such as architecture, engineering, and construction; product design and manufacturing; and media and entertainment. We empower innovators everywhere to solve challenges big and small. Like any business, we must carefully assess the value equation we offer customers: what capabilities can we offer customers in exchange for what price? Our aim is always to make such decisions a ‘no brainer’; the more such decisions are obvious and compelling, the longer our customers will remain invested in us and our solutions.

As chief of staff to our CEO, I have a role in ensuring these and other key topics are items on our staff agenda. I have been in a chief of staff role for nearly ten years across multiple leadership teams; at Autodesk I’ve helped architect a model in which every member of CEO Staff has a chief of staff, and I collaborate with that cohort to drive things operationally across the organisation. Chief of staff roles have also grown inside our company beyond this executive level, as numerous other VPs have made their own value calculations and decided it’s worth carving out budget to fund a chief of staff on their respective leadership teams. These two threads – the well-honed muscle around looking at things through the lens of ROI and the increasing prevalence of the chief of staff role – have driven me to reflect on the value of the role itself.

The Value Question and Why It’s Important

As the chief of staff role has spread into new domains, the initial and most common question has often been ‘what does a chief of staff do?’. In government and military contexts, this question was asked and answered quite some time ago. The question arose with greater prominence in the business context perhaps five to eight years ago, though it’s becoming less common now. Why? Because those of us in the role have worked over recent years to shed light on how the role can be designed for different situations, and therefore what the key responsibilities might be for someone in the role. I have attempted to be one of these voices, and I’ve written several articles focused on the chief of staff role published on LinkedIn and elsewhere. Overall, I see this trend as progress; fewer questions and greater clarity about what someone in a chief of staff role does signals that the role in the business context is maturing, and with maturation comes increasing professionalism.

But with this evolution, a new question begins to arise and take prominence. This question shifts the emphasis from what a chief of staff does to how he or she does it. ‘How’ gets into skills, tools, and methods; these things collectively add up to what we might call ‘performance’. Historically, assessing performance of a chief of staff can be quite subjective. In contrast

to other business fields such as sales or marketing, which are highly metrics-oriented, performance in the chief of staff role has been harder to nail down. In my experience talking to those who have a chief of staff, one can typically sense whether a chief of staff is ‘working out’ or not, but they struggle to express ‘why’ in clear terms.

Given my desire—and I assume the desire of anyone reading this article—to see continuous advancement and elevation of the chief of staff role, this is a problem. Our struggle to assess performance undermines the development of the profession. Furthermore, the inability to identify specific strengths or weaknesses makes it harder for any chief of staff currently working in such a role to spot development opportunities and pursue professional improvement. However, there is an alternative path: if we build on our track record of explaining what the chief of staff role is and start to pursue performance measurement for those in the role, performance and impact will rise over time and investment in the role will increase in parallel.

So, to pose our challenge as a question: how might we measure the value of a chief of staff?

Scope of Effort

As those reading this article undoubtedly know, the responsibilities of a chief of staff can vary from role to role. Chiefs of staff work in different organisational contexts (government, business, non-profit, etc.), at different levels, and across different domains, resulting in a variety of responsibilities depending on the situation. Given the variety of role definitions, any pursuit of measurement needs to begin with a target scope for the effort.

My experience is based primarily on the chief of staff role in the business context. In a prior article, I have asserted there are three potential orientations for the chief of staff role:

  1. The Principal. In this orientation, the chief of staff is there to enable the principal (e.g., the person for whom the chief of staff works) to operate at a higher level of performance.
  2. The Leadership Team. In this second orientation, the chief of staff is there to enable the leadership team to operate at a higher level of performance.
  3. The Organization. In this third orientation, the chief of staff exists to enable the broader organisation to operate at a higher level of performance. In this context, the chief of staff may operate much like a Chief Operating Officer for the organisation in question.

For the purposes of this article, I will focus on a chief of staff in a business context with a centre of gravity in Orientation #2, towards the leadership team. This orientation has been a significant portion of my experience, so I feel I can comment on it with some conviction. Furthermore, it is the most common orientation I see for other chief of staff roles in business. Although I’ll narrow the scope in this way for the purposes of this article, I hope those operating in different contexts or orientations can make straightforward extrapolations to their situations and extract value from the points below.

Measuring Value in Orientation towards the Leadership Team

My approach for assessing value in this context starts with a reflection on the orientation itself. What is a chief of staff there to do in orienting towards the leadership team? Increase the performance level of the leadership team.

‘What is a chief of staff there to do in orienting towards the leadership team? Increase the performance level of the leadership team.’

In any leadership team, each member of the leadership team oversees a set of key responsibilities and often an organisation. The goal of the chief of staff in this situation is not to improve the performance of any single leader or his or her functional area; rather, it’s to gain maximum value and impact from the time the leadership team spends together.

In the popular media, much is written about how meetings are often a waste of time. To be sure, poorly structured meetings with unclear purposes are, in fact, a waste of time. But these popular headlines miss an incredibly important point—the leadership team’s time together is
a critical factor in the success of the organisation. Any leader of a significant organisation has immense pressures on their time. When all such leaders come together as a team, it’s a rare and important moment for the entire organisation. Used effectively, this time turns into gold for the organisation. Wasted, it spells ruin.

This, I believe, is the foundational performance objective: any measurement of value for a chief of staff who seeks to continuously improve the performance of the leadership team (the essence of orienting towards the leadership team) must centre how well the collective leadership time is used, as this responsibility falls squarely on the shoulders of the chief of staff.

In Pursuit of an Equation

Ideally, measurement efforts can be distilled into an equation. Such representations, however imperfect, pull us away from the subjective and towards the objective. Pursuing an equation that helps to illuminate performance of the chief of staff might start with examining the components that contribute to the foundational performance objective outlined above.

If we consider a set of recurring meetings that a leadership team has scheduled, what are the factors that might dictate how well that scheduled time is used? In my experience, the key factors are the following:

  1. The Topics. What topics are getting onto the leadership agenda and why?
  2. The Cadence. When should the team engage on which topics? How might we balance known, important topics with late-breaking, urgent topics?
  3. The Design. How should the team engage on a topic? What data or information is prepared or shared in advance? How is the live discussion designed and facilitated?
  4. The Outcome. What is the outcome of the discussion? Who owns the next step(s), and what is the system of accountability?

In my view, the above four factors contribute greatly to the foundational performance objective. It’s worth unpacking these areas a bit more to uncover what high performance might look like. To this end, I think it’s helpful to think of these factors in the context of how a chief of staff might prepare for, conduct, and conclude a specific staff interaction.

Topics & Cadence

For years I’ve been asked this question: ‘how do you determine what the staff should spend time on, when the surface area of the team is so expansive?’ It’s a great question, and an important one. In my role, I consider two input streams:

  • Stream A pertains to things that, all other things being equal, merit the time of the leadership team in some periodic cadence.
  • Stream B pertains to things that were previously unknown but are now urgent and important.

For Stream A, it’s possible to build a finite list of topics that merit ongoing review, given the objectives and context of the leadership team. For an executive team at a large company, this list might include regular inspection of key business priorities and financial performance, organisational design, talent development, culture evolution, and a myriad of other things. The point is, the chief of staff can build such a list and validate it with the leadership team, arriving at a joint agreement; the list can evolve over time as the internal and external environment change.

Stream B is harder to plan for in terms of a finite list of topics because Stream B is, by definition, unknown. However, it is possible to plan for it in terms of capacity, or more specifically, reserve capacity. Said differently, we may not know what urgent and important topics might arise that merit attention (thinking over the past eighteen months, such topics could have included the global pandemic, social inequality issues, or extreme weather events, to name just a few), but we know something will show up and demand time, so we must assume some capacity relative to overall available capacity.

It’s worth taking a moment here to talk about the concept of capacity in a bit more detail. ‘Capacity’, as used above, refers to the amount of scheduled time on the calendar that the staff spends together. Depending on the meeting model, some executive teams may have a blend of weekly tactical meetings and less frequent strategic meetings, as well as other types in between. Capacity is the sum of all those scheduled hours over a given period. There is some minimum level of capacity that any team requires to function effectively; more capacity beyond that level is a choice of the leadership team.

In the context of preparing for a scheduled staff interaction, the chief of staff must critically assess the confluence of Stream A and Stream B and decide what the optimal set of topics are for a specific scheduled interaction. I believe this requires a mix of art and science. The science comes from the tools and methods the chief of staff might use to inform topic-by-topic cadence based on the seasonal flows of the executive team and the needs of the organisation. The art comes from judging when some of those planned topics need to be sacrificed and deferred in the face of new, urgent topics. A high-performing chief of staff will perform the art and science rituals above regardless of capacity; the operational assumption is that the capacity is fixed. We can always add more capacity (i.e., put more meeting time on everyone’s calendar), but that is rarely the preferred choice in my experience.

The Design & The Outcome

Topics, cadence, and capacity tee up the next critical element of the chief of staff role – how to approach a given topic discussion with the leadership team. The goal is to maximize the value and impact of spending time on the topic. To illustrate this, let’s consider the following hypothetical scenario:

  • a leadership team has an existing, recurring interaction coming up in two weeks; and
  • the entire meeting is scheduled for six hours, and there is one sixty-minute section that focused on Topic X.

Now, let’s consider two possible approaches to this scenario: the first approach is one with low value-add from a chief of staff, the second approach is one with high value-add from the chief of staff.

In the low value-add approach, the chief of staff ensures the subject matter experts for Topic X know their time slot for the meeting and prepare something to present. The experts show up at the meeting, present to the leadership team for forty-five minutes, then ask for input or guidance on a decision. The principal (the most senior person in the room) jumps in and offers her point of view. A few other members of the leadership nod and agree, others are silent. The fifteen minutes allocated for discussion time is exhausted, there is an assumption of a decision, and the meeting ends.

In the high value-add approach, the chief of staff takes personal responsibility for realising the highest quality outcome possible. Given this, there is much more planning that goes into the review of the topic:

  • The chief of staff might first pressure test the desired outcome of the session with the subject matter experts.
  • The chief of staff might suggest a pre-read or pre-watch be sent to the executive team seventy-two hours before the meeting to minimize one-way presentation time during the scheduled live session.
  • The meeting might start with a few minutes of a refresher on the topic at hand, then the chief of staff might open the discussion up for clarifying questions.
  • Next, to avoid a range of cognitive biases that might enter such a conversation, the chief of staff might facilitate a number of structured methods to ensure all members of the team are heard and the best ideas and insights are surfaced.
  • Finally, the chief of staff might verbally playback the understanding of where the team is landing in clear, unambiguous terms during the close of the meeting and then in written form within twenty-four hours of the meeting to ensure alignment on the outcome.

The higher value-add approach clearly looks and feels very different than the low-value add approach. And I can state with conviction that the high value-add approach delivers higher quality outcomes. Unfortunately, leadership teams without a chief of staff probably experience the low value-add approach all the time. And teams with a lower-performing chief of staff might even experience it occasionally.

Putting the Components Together

Let’s recap the ground we’ve covered:

  • we aim to measure the value of the chief of staff;
  • we defined the scope as a chief of staff working in the business context in Orientation #2;
  • we determined the performance objective (how well the collective leadership time is used);
  • and we identified core components that contribute to the stated performance objective:
    • Topics
    • Cadence
    • Design
    • Outcome.

Therefore, a chief of staff who performs increasingly well against each of these components should provide increasing value to the leadership team. Furthermore, any improvement in the sum of these components should equate to an increase in the value of the chief of staff. This is a big part of our measurement objective; it can be helpful for comparing one chief of staff to another, as well as assessing performance improvement for a chief of staff over time. But what does success ultimately look like? Is there a benchmark for high performance?

It’s my view that the critical benchmark is performance against the external comparison which is relevant for a given leadership team. In any increasingly competitive or threatening environment, the advantage often goes to the fastest. Building on this point, the four quality components described above – topics, cadence, design, and outcomes—must come together, blend artfully, and flow at a pace that meets or exceeds the pace for similar motions being carried out by the most relevant external comparison. In business, we can envision the leadership team of our biggest competitor next to ours. If our pace for reviewing, digesting, and making clear decisions on a balanced menu of long-term strategic topics, as well as urgent and important topics, exceeds the pace of the other leadership team attempting to do the same, I would argue the chief of staff is performing at a high level. It doesn’t always mean we will win; not every call we make will be the right one, and execution could falter, but the primary reason the chief of staff is there on the team is being fully realized. To represent this argument as an equation, we might construct it as follows.

PI(T + C + D + O) / PE(T + C + D + O)


  • P = Pace (of either the internal team or the external team);
  • T = Topics;
  • C = Cadence;
  • D = Design; and
  • O= Outcomes

If the pace and sum of our internal quality motions exceeds the pace of the quality motions of the external team, the numerator increases and the overall value increases.

Using the Equation

I believe this equation and the respective components can be helpful for diagnosing performance and identifying personal development opportunities. I have attempted to apply this formula to my own work as a chief of staff over the years. To provide some sense of what this thinking has driven me to do and develop, I can share some of the following details:

Topics & Cadence:

  • Some time ago I created an approach that I call the Topic Forecast. The approach is a combination of a tool and a set of processes; together, they support the ‘art and science’ rituals I describe above.
  • The tool is a visual reference that contains a living list of topics we believe the leadership team should spend time on at some regular cadence. I can map out when such periodic engagements should happen by month, and then I can link the monthly topics to specified recurring meetings.
  • In addition to this plan-view, I also mine for urgent and important topics in my regular staff interactions (as a group or in one-on-ones), as well as in my other interactions across the organisation.
  • These motions contribute to a specific, monthly proposal. At the beginning of each month, I send a message to our executive team that is my recommendation for specific topics mapped to scheduled interactions for the upcoming two-month period. Sending this recurring message allows me to get feedback, surface any other late-breaking topics I might be unaware of, and inform my final agenda-setting for any specific meeting. More generally, it allows our team to manage an evolving flow of topics in an efficient and planful way that is also agile and opportunistic.


  • I believe one of the most important skills for a chief of staff is facilitation. In this sense, I’m referring to a broad definition of facilitation, including the upfront design and preparation, as well as the live session management.
  • To this end, several years ago I embarked on a journey to develop my facilitation skills. I learned of the field of Human Centred Design (HCD) and the many methods and techniques that have emerged through that discipline.
  • As a company, we partnered with one specific firm (the LUMA Institute), and after my first two-day course it became obvious to me how powerful a method-based approach to facilitation could be for my job as a chief of staff. Over time, I trained to become an in-house instructor of these methods, and that work led to opportunities for me to facilitate executive-level briefings, customer workshops, and large-scale (100+ people) interactive sessions.
  • To this day, for any complex discussion, I lean on these methods and techniques. In some cases, I use a classic method or series of methods as designed. In other cases, I build off the principles and philosophies behind the methods to tailor them to suit my specific needs.


  • In terms of outcomes, my favourite question to ask a leader when we’re collaboratively preparing for an upcoming session is ‘what is the desired outcome?’ I have often found that leaders know when they want to have a discussion with a group of stakeholders about a topic, but they haven’t quite thought through how they might articulate the desired outcome in clear terms.
  • If we can write down the desired outcome in specific terms (e.g., ‘we end the session with a set of objectives, a high-level timeline, and a decision owner for this project moving forward’), then it describes to me what I need to do before the meeting to allow us to achieve that outcome as efficiently as possible.
  • For example, the above example might imply we need to send relevant information ahead of the meeting to allow the team to digest the proposal on their own terms. It may also imply the need for a design for the live session itself; we could use HCD methods that encourage divergent or convergent thinking, or perhaps prompt constructive criticism to pressure test the proposal.
  • My ultimate test for how well I’ve prepared for a given session is writing my post- meeting notes before the meeting. While this may sound strange, it’s actually not: if we have clearly articulated the desired outcomes, and I have designed a structured approach that is well suited to those outcomes, and I facilitate the session per the design and don’t get derailed, then I should, in fact, have a very good idea of where we will land. Of course, any such notes I write before the meeting are subject to our actual discussions, and I adapt them after the fact as needed. In any case, it’s a good test and allows for efficiency in playing back the actual outcomes following the session.

The above examples hopefully shed a little light on what pursuit of higher performance might look like for components of the value equation. I use the word ‘pursuit’ intentionally, because
I think performance improvement is never done, and there is rarely ‘one, best way’ to do something. I like to keep an open mind and experiment. To quote a sign I found on the wall when touring IBM’s Design Thinking headquarters in Austin, Texas: ‘Every Day is a Prototype’.


I believe the chief of staff role is engaging and rewarding, and I know those in the role can have an enormous impact on the people, teams, and organisations they are there to support. I love the idea of embracing our value and pressure testing if and how we can do more. I hope the above information advances our collective wisdom and prompts others to debate my points and build upon them.

Rob Dickins is currently Vice President & Chief of Staff to the CEO of Autodesk, a global leader in design and make technology. With nearly ten years of experience in Chief of Staff roles, Rob is passionate about contributing to field and has authored numerous articles about the role published on LinkedIn and Medium. Rob is based in the San Francisco Bay Area.


Further Reading

Dickins, Rob, ‘I’ve Logged 10,000 Hours as a Chief of Staff in a Large Tech Company; Here’s My POV on the Role’, LinkedIn, staff-large-tech-company-rob-dickins/ (5 January 2020).

Dickins, Rob, ‘The First 90 Days as a Chief of Staff’, Medium, robdickins/a-90-day-impact-plan-for-a-new-chief-of-staff-97768d9b04bd (22 March 2019).