Understanding the skills, responsibilities, and qualities of a successful Chief of Staff.
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Although it has been present in other industries for decades, the Chief of Staff (CoS) is a relatively new role in the technology industry.
The position started to trend when big technology companies like Google, Facebook, and Uber added Chiefs of Staff, but has since been adopted by organizations of many other sizes, including tens of thousands of those from 50-500 employees.
Thinking about hiring a Chief of Staff? Thinking you might want to become one?
In this article, we will dig into the nuts of bolts of the role.
A Chief of Staff is the right-hand to the company's CEO.
Unlike an executive assistant who deals with primarily administrative tasks, a Chief of Staff is someone in a leadership role that deals more with strategy and making high-level decisions for the company. They are involved in just about everything that happens at their company, but they're not always public-facing like the CEO.
“Be humble but confident — your role is NOT to be the star of the show, but rather to help the stars (especially the CEO) shine.”
— Megan Wheeler, CoS at Moves Financial
Chiefs of Staff often act as facilitators between different teams, ensuring that all parties are communicating and working towards the same goals. As a result, they are often the person at the company who knows most about how it operates.
“The role can be totally undefined by the principal, leaving the person with little to do, or it could become a glorified executive assistant, or it could be a roving project manager, or it could become a bottleneck gatekeeper, or it could be a second-guesser of strategies. I’ve seen all of these iterations.”
— Adam Kovacevich in Chiefs of Staff Are Necessary for Politics, But Not Always Great for Companies
A typical day can include helping with meetings, writing agendas, strategizing big initiatives at the company, getting feedback, and consulting with the executive team on tough decisions.
Chief of Staffs must have great people management skills, be able to handle a lot of pressure while making high-level decisions, and must be a champion of the leadership's strategic vision
1) People management: The CoS needs to be able to lead and motivate the team, facilitate communication between execs, ensure that decisions are being made correctly, etc.
2) High-level decision making: The CoS is someone that is tasked with making high level decisions for the company, like whether or not to acquire another company, how to handle large opportunities, etc.
3) Vision champion: A Chief of Staff needs to be able to understand what the CEO wants and make sure everyone in the company is executing towards it. This means you need a good understanding of your CEO's views and opinions on the market, the company, and the future.
Being a Chief of Staff is a multi-faceted role that requires a lot of experience leading people and projects. Anyone who wants this position should have previous experience working in a leadership role, either within their company or within a previous company.
In many ways, the qualifications are similar to that of the CEO. Many successful CoSs got into this position by working in a VP or C-suite role before becoming CoS.
Being a Chief of Staff is not an easy job. You need to be able to handle extreme pressure, deal with high-level personalities, and make tough decisions on a daily basis.
And, because there aren't many people with experience in this role, Chief of Staffs often find themselves faced with unexpected problems and challenges.
The job can vary depending on what stage your company is in. At earlier stages, the role focuses on advancing the company's vision and strategic goals. Later on, a Chief of Staff can be responsible for managing the team and helping the CEO scale their time across multiple teams.
“The literal title Chief of Staff can be deceiving, as Chiefs of Staff in most contexts aren’t managing any staff directly.
However, one of the primary functions of a CoS, having developed strong relationships with key stakeholders, is to be a conduit of information across teams.
This might take the form of developing company-wide OKRs and getting buy-in and support for the processes or running point on cross-functional projects that require 3 or more teams with no clear leader. In both instances the CoS supports the organization by freeing information bottlenecks, helping quickly growing teams get visibility outside their functional silos.
— Scott Amenta, ex-CoS @ Spring
Most Chiefs of Staff are hired internally. If you are managing other people, don't be afraid to take more responsibility and try to take on a leadership role. The more experience you have serving in senior-level roles, the better a Chief of Staff you will be.
First and foremost, you must be able to get things done. CEOs need someone who can make important things happen without them having to hand-hold. Getting things done is a Chief of Staff super-power.
CEOs need your help in both public and private matters. When they're in public (Q&A sessions, TV interviews, conferences), push them to be bolder, take more risks, and own it. But when they're in private (crisis mode, sensitive situations), make sure their back is protected.
As a CoS your decisions are likely to affect more people than you are used to dealing with on an average day at work. It's important that you learn how to provide feedback and direction in a way that's thoughtful, direct, and candid.
If you believe your company needs a chief of staff and that person should be you, it may also need to be you that brings it up. Because the role is relatively new, it's not an area a lot of companies are thinking about, despite needing someone to support the CEO and leadership team.
A Chief of Staff manages people and logistics while an Executive Assistant manages scheduling and admin tasks. Depending on an organization's size, there may be some overlap, but a Chief of Staff wields far more decision-making power than a typical EA.
The key difference between these roles is that a CoS runs the show (often in lieu of the CEO) while an EA helps their superiors run the show.
Many Chiefs of Staff say you need to be a "master generalist" to succeed.
“Take care of all the big things and little things that need to get done, but that aren’t exactly anybody’s job. Strategy, prioritization, and execution are key.”
— Megan Wheeler, CoS at Moves Financial
A Chief of Staff takes on many of the organization's toughest problems, yet rarely gets a stoplight on their accomplishments.
If you want to be a chief of staff, you need to be really good at solving other people’s problems. You also need to be okay with having to clean up problems that aren't your fault.
If you want heaps of credit, this probably isn’t the role for you.
The best way to demonstrate leadership is with your results. CEOs are looking for people who can define their own processes, set direction collaboratively, and execute on the vision without being told what to do every step of the way.
Problem-Solving Under Pressure
You will also need to be able to solve problems quickly and decisively.
Remember that you are usually the first point of contact for the CEO. If an issue arises, you should be able to recognize what needs attention and then figure out how the CEO would prefer it handled. You will need to be able to implement the decision and speak on behalf of the CEO.
Strong Communication Skills
As a Chief of Staff, you are working across many different people inside an organization—from the cafeteria to the board room. This means you need strong communication skills in order to get your points across clearly and be able to adapt when needed. You also need to have good written communication skills because you may have to write emails or speeches for the CEO.
A Meetings Master
Many Chiefs of Staff own the organization's most important meetings, preparing agendas and taking notes for weekly executive meetings, helping prepare the CEO for board meetings, all-hands meetings, and even putting together themes and even speeches for speaking engagements.
“Preparing board materials and strategy session decks for the CEO for meetings with the management committee and advisory board, preparing CEO for external speaking engagements (World Economic Forum, conferences, business school classes) as well as internal speaking engagements (investor meetings, firm-wide town hall meetings, etc.), researching trends and key themes for the CEO related to the private equity space as well as investment themes of important”
— CoS @ top growth-equity fund
“You should have some type of vision of what type of CoS you want to be — be that strategic, operational, HR/People, etc. The role is so nebulous that you need to understand what your strengths are, how you can be most useful, and most importantly, what you’re not going to do. It’s super important that your vision of your role and your principal’s expectations of you are closely aligned.
It’s a role that is extremely susceptible to scope creep, which means you need to have periodic (at least quarterly, if not monthly) frank discussions about your allocation. It’s a choose-your-own-adventure type of role, which is both a big opportunity and a big responsibility.
— Simon de Jesus Rodrigues, CoS at Curio
Thinking about hiring a Chief of Staff or recruiting one internally? Here's a job description template for a Chief of Staff that you can use in your job listing:
As the Chief of Staff at a fast-growing technology company, you'll be a strategic thinker and operational doer who will solely focus on the most critical organizational priorities. You'll report to the CEO, play an important role in executive leadership, and work as a cooperative partner across all functional departments of the firm.
The Chief of Staff's responsibilities include being a collaborator with the CEO as well as acting as a delegate on occasion. Your job will entail exciting and varied tasks across our global presence, and your success will be judged on your ability to boost leverage and velocity for the CEO and the rest of the executive team.
Responsibilities of the role:
• Work directly with the company's top executive to establish the organization's long-term objectives and day-to-day operations.
• Collaborate with senior leadership to develop long-term strategy.
• Run cross-functional projects with goals ranging from assessing progress, achieving goals, and motivating individuals to achieve their goals.
• Set the weekly executive staff meeting agenda, provide insights and analysis to assist in strategic debates, and track follow through.
• Take on special assignments at the request of the CEO, which may include everything from product development to finance and accounting.
• Act as a proxy for the CEO, advising key personnel on ways to achieve alignment on decisions.
• Take control over the content and agendas for significant internal and external reasons (such as investor meetings, board papers, key client meetings, internal all-hands, executive off-sites, and the like)
• 6-10+ years of experience working at a high growth tech company
• High EQ and comfortable influencing all levels of the organization
• Team-oriented professional with a commitment to driving both strategic and operational performance and improvement
• Self-starter with a desire to learn and evolve
• BA/BS Degree or equivalent practical experience
For more information, check out the State of the Chief of Staff in Tech report (2021), which is compiled from insights from a survey of 25 chiefs of staff.
Professional and personal development shouldn’t stop when you hit the management ranks.
To run a great meeting, keep the team aligned, and the agenda short, specific, and action-oriented.