LEADERSHIP AND MANAGEMENT
The Chief of Staff (CoS)
The CoS leads the CEO’s office. This is a quick summary of the CoS’s roles, responsibilities, required skill sets, and what it takes to be a successful one…
While traditionally the Chief of Staff sounded more of a political role such as that in the White House, today, it is becoming common in the corporate world. For example, in the startup and corporate technology sector, based on the number of hirings in the US, the Chief of Staff role has increased by double digits in recent years.
Who is a Chief of Staff?
The core responsibilities of the Chief of Staff
It’s not easy answering the question of what a Chief of Staff (CoS) does, because they’re all so different. But in short, a CoS is someone who plays an operational and strategic role to help the CEO, the executive team, and the company becomes more productive and successful. This will generally boil down into three main categories of duties:
- Operations. Helping manage the rhythm of the business through OKRs
- Communications. Helping develop leadership’s keynotes and narratives
- Strategic initiatives. Helping drive important, cross-functional projects
Characteristics of a successful Chief of Staff
A Successful CoS may not have direct experience in strategic initiatives or communications or operations, but they usually have five key attributes or characteristics, which are usually needed by any senior to succeed in any corporation:
- Business and functional acumen. Knowing how the business works, its vision, mission, and strategy, and how all the functions across the organization come together to achieve those goals
- Self-awareness. Knowing that people will be perceiving a CoS differently as the words they say and their actions will be perceived differently.
- Communications and trust. Because a CoS will work alongside senior executives whose schedules are packed, it’s key that the CoS communicates effectively, precisely, and succinctly. And only through consistency in communication over time, will interpersonal and organizational-wide trust is built. Furthermore, the CoS has to consistently deliver results and be sensitive and discrete around his/her confidential conversations and topics.
- The impetus for action. A CoS will manage multiple projects and stakeholders and deliverables and deadlines at any given time, and his/her ability to prioritize and get things done will be key to success.
- Growth mindset. A CoS, just like anyone else, will make mistakes. But it's his/her ability to reflect on and learn from those mistakes and not make them again that will be key to his/her success. A CoS needs to be inherently curious, always be asking questions, learn from mistakes, and possess a sense of resilience in the face of adversity.
Getting hired
There are three avenues to becoming a CoS:
- Active job search. Whereby one leverages his/her network and finds their path into a company and sees how it pans out.
- Changing a current role into a CoS. If your role is close in responsibilities to a CoS, then you can try to network and elevate your title into a CoS role through a senior executive’s consent.
- Hand-selected by an executive. Reach out to an executive who you admire and want to work for, describing your career goals and why you want to work with them. Understand why the executive needs a CoS and that it’s a real need and not just a good one to have as a painkiller. And be patient in the process as now may not be the right time.
Getting started: the first 30 days
There are 3 factors to consider in the early days of the role:
- Understand your role. Work with the CEO to draft a single page of your prioritized responsibilities so that you know the core of your duties. Based on this 1-pager, determine whether a team will be needed or not. If a team is needed then you will need a CEO’s Office. Understand that this document is a living one and will change over time, but this is a starting point.
- Build your relationships with the key stakeholders. In addition to the CEO, introduce yourself to the rest of the executive team to build productive relationships with them, as the COS’s job will be to make the entire executive team more productive and successful. Share your core responsibilities with them and make sure they understand your role, your background, your interest, who you are as a person, and that you do the same for them and that you learn about their world as well. Ask what they think is going well in the company and where there can be improvements as well as their recommendations. Ask them who else on their staff you may need to talk to, to better understand their needs such as the Personal Assistants including the CEO’s EA. Gradually build a weekly schedule meeting with these stakeholders to align on needs, priorities, and projects.
- Built your reputation. In the first 30 days, all eyes will be on the CoS. People will be wondering who you are and what you’ll be doing. Therefore it’s key to over-communicate and over-deliver. Try to achieve small early wins and celebrate them as a team with the CEO and the executives in a subtle manner.
Winning in the role
1. Operations
Operations in the rhythm of the business or the cadence of key meetings and processes that help drive the company. A successful CoS needs to understand his/her role in driving this cadence. Every company has a different rhythm, for example, smaller companies may have fewer meetings, whereas larger companies may have more.
To succeed in helping operations, the CoS will need to map out the rhythm of their operations such as the key executive team meetings, off-sites, quarterly reviews, board/investor meetings, customer conferences, etc. And with this map in place, start to understand:
- How often do they occur
- Who are the people involved in driving them
- What success looks like, what are the metrics and OKRs
- What the process is to achieve this success
With this map in place, understand what the CEO wants the CoS to play in these meetings and processes, to do whatever it takes for the organization and the CEO to be more productive and successful.
2. Strategic initiatives
Strategic initiatives are projects that the CoS will lead or co-lead on behalf of the CEO and the executive team which can range from an urgent one-week project such as quarterly sales planning to a 4–6 months market entry or raising capital project, or even a multi-year transformational or change effort. Regardless of the duration and the intensity of the project, to succeed with strategy-related initiatives:
- Engage the right stakeholders across the organization. In the CoS role, someone else in the organization is going to feel like you are doing their job, in other words, overstepping on their boundaries. Therefore it is important to engage the key stakeholders early on and align on the goals of what you are doing and take the time to bring them into the loop. Ask the relevant executive member who they want from their team to be a part of the cross-functional team and make sure to have a direct communication line to keep them informed of the project's progress.
- Raise awareness of the projects. Send weekly updates to the executive team, talk about and present the projects during staff meetings, and make sure that all stakeholders are clear about the current status and next steps.
- Transition projects to the organization. Work your way out of the project (i.e. exit the project). For this to happen smoothly, onboard the project champion early on, and then carry it onto them as part of their job when the project is ready to be delivered.
3. Communications
Given the close working nature with the CEO, the CoS is in a position to help drive key communications, such as keynotes and presentations; but he/she will need to have a great relationship with the CEO and know what’s top of his/her mind and agenda. Aim to partner with the communications team to develop internal and external presentations.
But do not work in a silo with the CEO. Fruitful communication only happens through highly collaborative cross-functional efforts. Therefore, engage any stakeholder across the organization who can help make the narrative better and crisper. Define roles, responsibilities, and expectations to avoid overstepping or duplicating efforts.
Understand how the CEO prefers to develop his/her keynotes. While some are top-down driven with a prearranged narrative, others are more bottom-up where they prefer a collaborative and iterative approach to develop content.
Make the journey yours — enjoy it
- Take it slow. While you may have a lot of ideas, don’t exceed the organization’s ability to take those ideas. Bring others along with you on that journey as you aim to achieve change and growth in the company.
- Be the CoS. You don’t need to use the CEO’s name all the time to get things done. When you bring up the CEO’s name too often, you lose your power and downgrade yourself to a messenger. Unless you need to for example when it’s urgent, or a crisis mode.
- Define your goals and expectations. Shape your experience as the CoS. Having a good sense of your career goals will help you spend your time in the CoS role in the right ways as this is a great networking opportunity internally and externally.
- Have gratitude and humility. The CoS will be interacting with various people in the organization and will witness how they come together to accomplish goals. Because of the CoS’s unique role, everyone’s on his/her team and the CoS needs to work collaboratively with many people simultaneously. Therefore, it’s important to take time to recognize people’s efforts to help you achieve your tasks by sharing your gratitude and helping them feel appreciated for the work that they’re doing.
Every CoS role is different. But it is also a very fluid and salient experience. Therefore it is up to the CoS what he/she makes of it — hopefully a meaningful and impactful experience. If you are given the chance to become the CoS, take the chance and embark upon the experience to drive change and impact across the organization.
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