Unleashing the true potential of the Chief of Staff role

This article is a part of “10xInsight” series where startup leaders share bits of insights from their growth journey. 

Before we begin, we want to thank Nishad Kenkre for giving shape to this detailed article on what a Chief of Staff could do and all the things you wish someone would tell you about the role.

Nishad Kenkre is currently Chief of Staff at Swiggy, one of India’s largest tech unicorns. In a former life, he used to head up Strategy at Disney India and produce Broadway stage musicals for Indian audiences.

Nishad strongly believes that discovering or creating something new that others find useful, is the ultimate joy. He is deeply passionate about consuming as well as developing intellectual property in the fields of Managerial Effectiveness, Organizational Design, High-Performance Culture and Consumer Psychology.

Over to Nishad…

Let me start with a disclaimer. In stark contrast to how fancy it sounds, the Chief of Staff role (hereafter abbreviated as ‘COS’) is one of the most ambiguous and unconventional leadership roles in the modern organizational structure. It also functions largely behind-the-scenes and despite the high level of responsibility, rarely comes with equivalent formal authority. And all of this is by design. Therefore, it is not a surprise that up until a few years ago, COS positions in the Indian corporate realm were uncommon, poorly understood and rarely set up for success.

Not anymore, though. The multi-fold increase in organizational complexity and growth pressures over the last few years has led to a surge in roles that add to leadership leverage. And the COS role is certainly one of them, currently seeing a high level of interest from CEOs and industry leaders across various sectors.     

So what is the ideal job description for a COS? The answer is – “It Depends”. And in this case, it really does, because there is really no one-size-fits-all to what an organization might want out of its COS. It depends on everything from the CEO and their leadership style to the life stage of the company to the organizational culture (and many other factors). 

There is a spectrum, however, that captures the different types of COS profiles that companies have implemented successfully. On the left extreme of the spectrum is the “EA to Chairman” type of positioning, which Google describes as “providing 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 “Co-pilot to CEO” type of positioning, which unfortunately does not have a description on Google as it is also the path less trodden, but essentially refers to truly partnering with 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, right from the recruiter brief to the hiring process to the title and compensation to the job description to team staffing, will depend on this. Hence, having this clarity is a pre-requisite of epic proportions without which the company might as well as just discard the idea of hiring a COS altogether.

To supplement the above with a personal anecdote – When I was approached for the COS role at Swiggy, the very first conversation made it abundantly clear that the company had given a lot of thought to the kind of COS profile they wanted (in that specific case, it was the “Co-pilot to CEO” positioning). Every single person I met in the course of my interactions  gave me a very clear and consistent picture of the WHY (WHY this role and WHY you) and the WHAT (WHAT we want this role to accomplish). Looking back, I feel certain that this was the single most important factor that inspired trust and confidence in both parties. 

Interestingly though, the HOW of it was a complete blank slate, and till date, I am not sure if that was by design or simply a side effect of the blitz-scaling that was going on at that point. Either way, it did feel like being thrown into the deep end of the pool….or maybe ‘ocean’ is the right word to use :). But with the benefit of hindsight, I can today see why it was a good thing. It allowed me and the pilot of the ship (i.e. the Co-founder & CEO) to organically co-develop a charter that was tailored to suit the specifics of our context and ambition. 

Through the rest of this article, I have attempted to deconstruct this HOW in as universally applicable a manner as possible. So here goes.     

In my experience, any Chief of Staff can structure their role around 5 Ps. These are essentially 5 mutually exclusive charters – People, Planning (+Program Management), Performance, Processes, and Projects. This framework is fairly exhaustive – most variants of the COS role will have the same charters at their core, although the desired depth within a particular P might vary. 

Let us take a closer look at each of these charters.

People

This charter consists of two major components – Managing the CEO’s Staff (as called out in the title ‘Chief of Staff’) and Organizational Design (“are our best and most relevant people in charge of the most critical aspects?”). The former involves facilitating regular, often weekly, Staff Meetings of different leadership clusters on behalf of the CEO, with the ultimate aim of ensuring that the highest leverage topics of the company relevant to that cluster are surfaced and addressed consistently. Examples are many – 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 needless to say, 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 goals and priorities in any given performance cycle 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 and sometimes the CFO, with close guidance from the CEO. For instance, at the onset of a macro externality like COVID, an ideal COS would brainstorm with the CEO to understand the key pivots that the company needs to make and then finalize how best to bring them to life with the right talent/resources. 

Planning & Program Management

For any COS, this is perhaps the biggest charter of all in terms of both mindspace and impact. Unless a company has a designated Head of Planning (more likely in traditional publicly listed companies with strict reporting requirements), this charter typically falls under the ambit of the CEOs Office and is led by the COS 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, deconstructs them into projects/initiatives of varying complexities, allocates resources to each, and finally ensures perfect delivery through project management. In a tech company, there is the added complexity of product planning, i.e. prioritizing products for the engineering roadmap, allocating bandwidth across engineering teams, bin packing for efficiency and overseeing delivery through deep program management. This exercise involves a very high degree of stakeholder management across business, product, engineering, design, analytics and data science. Typically, CEOs of tech companies are closely involved in product planning (with some even choosing to play the role of CPO), thereby further amplifying the role of the COS in this charter. Although not conventional, sometimes the COS can also be tasked with leading the Program Management Office to ensure greater control of end-to-end delivery. 

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 often not formalized in fast-paced organizations but is effectively the other half, alongside Planning, of what drives companies to deliver predictable performance quarter on quarter and inspire confidence among investors. Simply put, this charter aims to track the journey of the impact/goodness of every major initiative 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 every initiative – right from estimation to financial accounting to final delivery, and focuses on the WHY of all deviations. Doing a continuous ‘retro’ of deviations in expected performance not only ensures accountability but also adds to the organization’s collective intelligence and helps eliminate systemic gaps. This is typically instituted through a regular cadence of WBRs/MBRs (Weekly/Monthly Business Reviews). 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 that bring alive its Culture Code. Typically, a COS will take charge of designing and implementing organizational processes that are applicable to a large part of the company and can provide high leverage (vs business processes that solve for specific business outcomes). The key is to continuously challenge the status quo and obsess over how things can be done faster and better within the given resourcing constraints – something that is a definite top-of-mind topic 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 practices that the entire global workforce breathes on a daily basis. 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. This can cover everything from productivity improvement (for e.g. – a process or ritual that helps cut down ‘meetings’ by 50% without changing outcomes) to quality check mechanisms (for e.g., a comprehensive documentation template for all new ideas to help maintain a quality bar) to information systems (e.g, an automated broadcast system to notify regional teams real-time of any product launches or modifications)  

Projects

The COS can also be tasked with leading strategic projects that require a central vantage point and greater-than-usual CEO oversight. Most times, these are projects that emerge from visioning exercises or long term strategy discussions and need some degree of structuring and solutioning at central level before being passed on to functional teams (for e.g. exploring new service lines or helming a restructuring exercise). In rare cases, these can be projects that are run end-to-end by the COS and their team, but those need to be exceptions as too much depth threatens the overall leverage of the COS role. In relatively early-stage organizations, the COS can also be asked to dual-hat as Head of Strategy, in which case the Projects charter would be significantly amplified.

In Conclusion

There are many layers of depth to each charter which I have not covered above. And possibly, there are charters that I have not even discovered yet (although I sincerely hope the new charters I uncover start with the letter P :)). Still, as I sign off, I hope this article was able to add some value to what you already knew about the Chief of Staff role and I hope it leaves you with at least a couple of powerful insights around how the role can be structured for maximum impact.

If you could spare 30 seconds before you leave…

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