The Silent Strategist: Demystifying the role of the Chief of Staff

Let me start off with a disclaimer. In stark contrast to how fancy it sounds, the Chief of Staff role is one of the most ambiguous and unconventional leadership roles in the modern corporate structure. This role has its origins in military settings, particularly in the armed forces, and it traditionally refers to the highest-ranking officer assigned to the commanding officer, responsible for coordinating and managing the staff operations. Over time, the concept of a Chief of Staff extended beyond the military domain and found its way into corporations. However, it has always been a rare position (typically there is only one Chief of Staff in an organisation at a given point in time), and one that mostly operates behind the scenes. Because of these reasons, the awareness and understanding of this role among corporate leaders is still nascent and you’ll find many instances where a Chief of Staff is hired but not really set up for success.

It is not all gloomy though. The future looks pretty bright. Organisational complexity is increasing, while the age and experience of the average CEO is falling. This has led to a surge in demand for roles that add to CEO leverage, and the Chief of Staff role sits right on top of that list. I held the Chief of staff role at Swiggy for nearly 2.5 years, and during that time I saw a rapid increase in both, the number of CEOs who wanted to hire a Chief of Staff for their office as well as the number of professionals who wanted to play that role

It is important to note that the Chief of Staff role can exist in various avatars across a spectrum. On the left extreme of the spectrum is the relatively junior ‘EA to Chairman’ avatar. Google describes this as?“someone who provides a comprehensive organisational, administrative and programme support service to the Chairman by proactively overseeing the Chairman’s workload and completing tasks as directed by the Chairman”. On the right extreme is the most senior ‘Co-pilot to CEO’ avatar. Here, the Chief of Staff is expected to play a true partner to the CEO in all matters of thought leadership, planning, execution and people management. It is ultimately up to the CEO and the Management to figure out where they want to operate on this spectrum. Every single aspect of the hiring process — recruiter brief, JD, title, compensation, team staffing, and so on — will depend on this. Having this clarity is a pre-requisite of epic proportions without which the organisation might as well as just discard the idea of hiring a Chief of Staff altogether.

Lets now move to the main question — What exactly does a Chief of Staff do?

In my view, the role of a Chief of Staff is structured around 5 Ps. These are essentially 5 mutually exclusive charters People,?Planning,?Performance,?Processes, and?Projects

Let us take a closer look at each charter.

People

This charter consists of two major components — Managing the CEO’s Staff and Organizational Design. The former involves facilitating regular (often weekly) Staff Meetings of different leadership clusters on behalf of the CEO. The objective is to ensure that the highest leverage topics relevant to each leadership cluster are surfaced and addressed consistently. Examples are — CXO Staff Meeting, Product Staff Meeting, VP Staff Meeting, and so on. The true measure of success here is in being able to get the wider leadership of the company to function as a single cohesive unit, and this requires the deployment of both IQ and EQ in equal proportion (“How To Run Staff Meetings for Maximum Impact” can be a playbook in itself).

The latter — Organizational Design — is a ‘soft’ charter that is sporadic in nature, but high impact nonetheless. This requires the COS to be in sync with the CEO on the key priorities of the organisation and ensure that these are staffed and resourced appropriately and well in advance. Very often, this exercise is done in partnership with the Chief People Officer with close guidance from the CEO. For example, at the onset of a macro externality like COVID, the Chief of Staff would brainstorm with the CEO to understand the key pivots that the company needs to make and then figure out how best to bring them to life with the right talent/resources.

Planning (+ Program Management)

For any Chief of Staff, this is perhaps the biggest charter of all in terms of both mindspace and impact. Unless a company has a designated Head of Planning, this charter typically falls under the ambit of the CEOs Office and is led by the Chief of Staff working closely with the CEO. The one-line objective here is to develop, institutionalize and execute a tight planning process that takes in the goals and priorities of the company as inputs, converts them into a strategy and operating plan, and further translates them into goals for each leader. Many companies follow the OKR process, but in my view it is up to the Chief of Staff to figure out what works best for their company. The Chief of Staff is also responsible for ensuring timely delivery of projects/initiatives of the operating plan through rigorous program management - in many companies, this is done via a Project Management Office staffed with skilled PgMs and falls under the ambit of the Chief of Staff. In a tech company, there is the added complexity of product planning, i.e. prioritizing product initiatives in line with the overall strategy and allocating bandwidth across engineering teams. Needless to say, the Planning charter involves a high degree of stakeholder management across a large number of teams.

Side note — Product Planning is a complex and still evolving field and is widely discussed and debated in tech communities across the globe. Over and above the inherent complexity, it also needs to be tailored to the cultural specifics of the company for the highest effectiveness, making it one of the most challenging problem statements on the plate of a Tech CEO.

Performance

The Performance charter is focused on ensuring that the company delivers predictable performance quarter on quarter, and assumed even more importance when the company is listed. Simply put, the objective of this charter is to track the impact of major initiatives undertaken in a given cycle and establish a strong feedback loop for greater predictability and accountability. Most large-scale companies aim to deliver anywhere between 50–100 significant projects/products every cycle scattered across teams and timelines. Yet, whether the company delivers on its promise to investors or not is almost entirely dependent on the sum total of how each project/product fares vs expectations. This requires setting up and running a systematic process that tracks the impact of these initiatives, right from estimation to interim reviews to eventual impact, and then focusing on understanding the root causes of deviations. The latter is typically instituted through a regular cadence of WBRs/MBRs (Weekly/Monthly Business Reviews) and the takeaways from these rituals add to the organization’s collective intelligence and help eliminate systemic gaps. In most companies, this charter will also feed into the Performance Appraisal system run by HR, helping drive objectivity and fairness in talent development.

Processes

The bigger a company grows, the more critical it becomes to lay down clear Ways of Working and institutionalize them in the form of rituals and processes. Typically, a Chief of Staff will take charge of designing and implementing large scale processes that are applicable to a large part of the company and provide high leverage (vs business SOPs that solve for specific business outcomes). The key here is to continuously challenge the status quo and obsess over how things can be done faster and better within resourcing constraints, which is deinitely top-of-mind for any CEO. Companies like Amazon owe their success in significant part to a whole bunch of processes and rituals that were conceptualized in the early days to solve for inefficiencies or productivity gaps and later went on to become well-entrenched global practices. There are 3 parts to this charter — opportunity identification, process design, and institutionalization. Ultimately, how well a particular process is designed determines whether or not it is widely adopted, which in turn determines whether the gains from it are permanent. The scope is broad and covers everything from productivity improvement (for e.g. a set of rules that help cut down ‘meeting time’ by 50%), to quality checks (for e.g. a template to pitch all new ideas), to information systems (e.g, a broadcast channel to notify on ground teams of upcoming product launches).

Projects

The Chief of Staff can also be tasked with leading strategic projects that require a central vantage point and close CEO oversight. Typically these projects emerge from corporate strategy discussions and need some degree of solutioning at the central level before being passed on to functional teams for execution. In rare cases, the Chief of Staff might choose to run these projects end-to-end. In early-stage organizations, the Chief of Staff can also dual-hat as Head of Strategy, in which case the Projects charter is significantly amplified.

While the 5P framework is fairly exhaustive in a global sense and most Chiefs of Staff do have these five charters at the core of their job, it is not by any means a one-size-fits-all. The weightages given to each P will vary significantly from organisation to organisation, depending on the most critical needs of that unit at a particular point in time. At the same time, the framework goes to show how the Chief of Staff role entails a very high span and can be critical to the smooth functioning of an organisation.