The Chief of Staff Playbook.
In 2015, after moving to America from Europe, I graduated from the University of Southern California School of Law. However, I was unsure what to do next with my career. I knew only one thing: I did not want to be a lawyer anymore. Living in California, with its rich tech ecosystem, made me realize the wealth of opportunities available to me. I wanted to be part of it in one capacity or another.
I worked for a Venture Capital firm for a year and then joined a young startup as their Chief of Staff (CoS) before becoming their Chief Operations Officer (COO). I quickly realized that the distinction between these functions is primarily semantic in smaller companies, as they both support the development and implementation of the CEO’s vision.
After five years with this company, having built a startup with 120 employees that generates an eight-figure annual profit, I made a successful exit following a long yet fascinating M&A process and went on to do something else. However, I want to share my experience with CEOs and aspiring CoSs to shed light on what this position entails.
So, who is the CoS exactly?
Even though the position of CoS is becoming more popular, it remains obscure to many. I came across the concept of in college when I became an intern for the Secretary of Defense’s CoS in my country. This position originated in politics and was later adopted by the business world.
Every CEO of a fast-growing startup or large company faces the same issue: time. There are more interesting projects, ideas, and meetings to engage in every day than hours in a month. This is where the CoS brings value to the company by offering additional executive hours to the CEO’s schedule. However, the CoS is not an executive assistant or a glorified one. Executive assistants play an essential role in companies, helping the CEO or other executives with tasks such as calendar management and travel reservations. However, their prerogatives remain limited to administrative issues. This is an important distinction; an executive assistant takes care of time-consuming yet highly delegable tasks, while the CoS is part of the executive team and works autonomously.
The most outstanding CEOs are those who have both long-term vision and the ability to manage the day-to-day running of an organization effectively. This is a daunting task, which is why a CoS is beneficial. The latter plays the roles of communication enhancer, strategy planner, operations enforcer, and truth-teller. The goal of the CoS is to help the CEO run the company as smoothly as possible. He is a little like an in-house consultant for the company or a “junior COO.” At times, the roles of CoS and COO may become blurred, especially in smaller structures.
So, what concrete tasks does a CoS perform? This all depends on the organization’s structure and needs. Some skills and tasks are consistent across the board; others vary and are dictated by circumstances.
What tasks does the Chief of Staff handle?
1. Day-to-day operations
A good CoS should think through and establish systems and make sure they are effectively implemented every day. Whenever I talk to a startup founder who mentions growth issues, I ask them what systems and processes they have in place. I find it astonishing that most do not have any. Developing systems is often perceived as a waste of time and something that can be delayed to a later date when things are calmer. But systems are at a macro level what habits and frameworks are for an individual. Sure, they take time to create and even more time to implement. But as Aristotle said, “We are what we repeatedly do. Excellence is not an act, but a habit.”
This is also true for organizations such as startups. I believe in systems and processes, especially when a company is in growth mode, which is when its foundations are built. Systems and processes clarify expectations, ensure consistency, and facilitate seamless transitions when new team members are onboarded. Creating systems is far more time-consuming than people think, but the output is impressive.
In an organization without a COO to build the company’s backbone on an operational level and with a CEO who mainly focuses on generating revenues (as they should), a CoS can help develop these systems. The CoS is perfectly positioned to understand the big picture and can dedicate time to handling such a project.
In concrete terms, this process starts with the creation of a well-defined organizational chart. This ensures that everyone knows who does what. Every position on the chart should have a highly detailed job description. For each “requirement” in the job description, a step-by-step explanation of the tasks should be drafted. This may seem as if it would only be significant for repetitive tasks and “lower-level” employees. However, it can be surprising how many tasks can be streamlined when thought is put into how best to perform them, even at higher levels. Finally, for each position, KPIs and OKRs must be added to establish appropriate expectations. These documents should play an important role in the onboarding process, and new hires should be given time to absorb them. I have helped create these systems at every level of a company, and they have led to less stress, more consistency, less micromanagement, and increased happiness overall.
If a department is not running smoothly, it is often because of two things: a management issue or a system issue (which arises when tasks and company demands are unclear). Both issues can exist at the same time, and they often do. And a manager who chooses chaos over order is probably not a good fit for any organization. But there is no excuse for an absence of systems. One book helped me to understand the importance of systems and how to build them: The E-Myth Revisited by Michael Gerber.
2. Internal and external communication.
Effective communication requires repetition, repetition requires time, and CEOs often do not have an abundance of time. Hence, the CoS can help to transmit important messages within the company, linking the leadership team with the broader organization. Often there’s a better way to handle the information flow necessary for a CEO to succeed, and very often, the CoS can play an essential role in amplifying and improving the CEO’s communication.
This is especially important in modern companies, which tend to be highly siloed and in which different departments do not always communicate with each other effectively or at all. So, if the CEO defines the general line, the rest of the management work on implementing it. For the CoS, this means two things:
Top-down communication: This entails crafting a compelling message for the CEO; organizing weekly, monthly, and annual strategic meetings; following up with various stakeholders; and building effective presentations. My secret sauce for outstanding presentations is a course called Visualize Value.
Bottom-up communication: An effective CoS should investigate what is happening in the company, with greater diligence and attention to detail than the CEO would have time to exercise and report back to the latter. They can do this by providing effective feedback on ideas and proposals from team members.
For example, my company had three locations in three different countries. We created a monthly newsletter that was sent to all team members and a monthly virtual meeting for all managers so that they understood who was doing what and how they could help. To be effective, these meetings should be organized by someone who has a broad view of the company and the time to organize them, namely, the CoS. In some instances, especially in venture-backed companies, the CoS can also take care of external communications with investors and, more rarely, the media.
3. Advice and strategy
Another crucial element of the CoS position is its advisory role. The CoS should be a truth-teller and have a broad understanding of the company and the industry. They should be able to provide insights and strategic ideas to follow. While a CEO’s other direct reports typically emphasize their specific areas of the company, a CoS should consider the needs of the whole enterprise.
That could take several forms: holding the CEO accountable for his commitments, ensuring she is accessible and open to new ideas and proposals; ensuring she prioritizes the right things.
I pride myself on having played that role during the M&A process that my company went through. I helped to build a solid valuation, prepped M&A presentations, handled some of the negotiations, and worked for the application of the sale contract.
4. Project management
Any good executive must have a whatever needs to be done attitude. This is especially true for a CoS, whose role is often close to that of Project Manager, as not every high-level project falls into a specific company department. The CoS should lead high-priority business initiatives from conception through to successful execution while collaborating cross-functionally. In my case, I had to handle the payment of VAT (value-added taxes) within the European Union from the US and the creation of an online merchandise store for our brands. Suffice it to say, I did not get bored.
5. Research and analytics
If CEOs were offered a few extra hours every day, they would explore new ideas and potential projects in greater depth. I have been lucky to meet some successful entrepreneurs since moving to the US. Often, when learning about their business, I ask them why they are not exploring other ways to monetize their product. I want to understand why they are not pursuing different ideas. Sometimes, there is a valid business reason behind these decisions, but more often than not, they just lack time. One of my favorite tasks as a CoS was to wear my analyst hat. This involved learning about alternative monetization avenues, new management concepts, and better software and tools and presenting them to my CEO when I thought they made sense.
6. Human Resources (HR).
Depending on the size of the company and whether there is already a Head of People, the CoS may get involved with the HR department (to deal with issues such as compliance, culture creation, and work from home policies for instance). However, there are two elements of HR with which a CoS should always be involved:
- Taking the pulse of the company. It is essential to stay in touch with the team and take care of internal issues before they become too serious to ignore. Some of this work can be automated. In my company, we used OfficeVibes, a software package designed to take a company’s pulse and assess team morale. Once an issue becomes known, it is equally important to follow up to address it, even if only to dismiss it (sometimes the record needs to be set straight). I have noticed that good employees often do not complain about issues; they quit, which is a shame when those issues can be prevented.
- Recruiting top talents. Two internal factors can set up a company for success or failure at its inception: effective systems and good talent. Hiring is a science, albeit a time-consuming one, that should not be neglected. The CoS can select and interview candidates and develop the hiring process to find the best employees.
7. Finance and legal
At times, the CoS may handle various executive tasks. As a former lawyer myself, I was often the direct point of contact for our lawyers until we hired a legal department, and even then, I oversaw their work on behalf of the CEO.
I also handled some financial projects, such as creating budgets and financial projections, until we hired a CFO.
Of course, these should be handled on a case-by-case basis.
What’s next?
Because of the intensity of the role, a CoS rarely stays for more than two years, after which they often transition to an executive position within the organization. In smaller companies, this could be the position of COO (as in my case). In bigger structures, they may take a VP or senior manager role. Reid Hoffman’s former CoS, Sarah Imbach, is now the COO of a large company.
This is also why it is so important to structure the CoS roadmap ahead of time. A useful example of a development plan for a CoS is presented below.
To conclude, the CoS’s value should be judged on three aspects:
1. Clarity: This relates to the vision of the company, the depth of analysis, strategy brainstorming, and “desiloization.”
2. Productivity: This concerns hiring and firing, analysis, and delegation of important yet time-consuming tasks.
3. Structure: This relates to the creation of solid systems.
I hope this playbook has been useful. If you have further questions about the CoS adventure, please email me at john.delfau@gmail.com or on LinkedIn.
