Seven reasons you probably don’t need a Chief of Staff

I’m Max Bray, and I’m Chief of Staff at Founders Forum, Europe’s premiere founder community, and a family of businesses that exist to support entrepreneurs at all stages of their journey.

—

The recent furore over Boris Johnson’s Chief of Staff (CoS) appointment echoes a broader debate in the offices of CEOs and tech founders; namely, that as of November 2020, the position has rapidly become the must-have next hire for any self respecting founder, CEO or senior minister.

In fact, a Google for Chief of Staff roles in the UK highlights more than 50 current open positions, everywhere from early-stage start-ups, funds and family offices, through scale-up successes Revolut, Depop, to institutions such as the University of Warwick and Track and Trace UK.

As a quick reminder, a Chief of Staff is broadly defined as one who acts as a leader’s right hand and trusted adviser. They work directly with a CEO or C-Suite colleague, and build strong relationships with team members across their organisation in order to influence outcomes and maintain momentum. CoS’s generally have a bird’s-eye view across teams and departments, allowing them to make connections in ways that others can’t.

Given the rapid popularisation of this still poorly understood position, it felt relevant to engage not only with when and why organisations should hire a CoS, but also when the conditions aren’t right to set them up for success.

As such, I spoke to a number of CoS’s across start-ups, scale-ups and big tech to understand when not to hire a Chief of Staff, ideally to help CEOs properly think through their needs, and whether a CoS is indeed the right hire for them. Thanks to Jess Houlgrave (Checkout.com), Ashleigh Otter (Perlego), Penny Penati (Laka), Sarah Matthews (Monzo), Isabel Sanchez (Zoopla), and Scott Amenta (Chief of Staff Network, Spring) for their thoughts.

1. You don’t know exactly why you want one

A desire to be able to say “My Chief of Staff will handle it” is not a sufficient reason to hire one.

In fact, without clarity on who you think you need, or what you’re hiring them to do, you’re not setting yourselves up for success.

All of the CoS’s I spoke to noted the importance of starting the job with a clear understanding of what needed to be done, especially so as they were all first time Chiefs of Staff, and generally the first incarnation of the role in their particular organisation.

“CoS is a less well-known position within many organizations- it is crucial to lay out what the role is and what it is not” — Emma Ainley, Chief of Staff at 500px

Therefore, as a CEO looking to hire a CoS, especially for the first time, it is vital to have clarity on what needs solving, and indeed what type of individual is needed to assist in that process.

Richard McLean has done an excellent job breaking down various frameworks for understanding and clarifying the role, categorising the position by key function. Similarly, Harvard Business Review splits the role into three broad levels in their “Case for a Chief of Staff”:

1. Level 1 — typically an ex-Executive Assistant, who oversees use of the CEO’s time, always ensuring she is prepared and focused on the most important issues, and who also manages (generally internally-focused) special projects for other CxOs.
2. Level 2 — an ex-MBA-type who works more on external-facing business development, R&D, and new initiatives with heads of departments, spending less time working directly with the CEO and managing their inbound or activities.
3. Level 3 — A senior and experienced gatekeeper in a large organisation undergoing “strategic, operational, and cultural change” (especially when the leader is newly appointed). This CoS is most like the political or military incarnation, managing the office of the CEO, executing their plans and ensuring they are always prepared.

These three types broadly chart to organisation size, with smaller and earlier favouring one or two, then larger and more mature looking more like two to three. They are not mutually exclusive however, and no CoS I have spoken to fits perfectly into any one category.

However, engaging with frameworks for role definition should be helpful for anyone looking to hire a CoS for the first time, or indeed as an organisation changes.

2. Your organisation is too small

“Not all situations have the right blend of organisational dynamics, market factors, and leadership style that lend themselves to a successful incarnation of the role” — Tyler Parris

Chiefs of Staff are better suited to larger organisations.

Given the nature of the role — working directly with the CEO to communicate their will, free up their time, and work with the C-suite as a gatekeeper for information and birds-eye-view across multiple work-streams — there just isn’t the same need for a CoS in a small or early stage business.

If you’re running a smaller company, consider whether this employee might be better suited as a Special Projects hire, Operations Lead or another broad title that doesn’t come with the specific connotations of a Chief of Staff.

To help assess suitability, Tyler Parris’s “Chief of Staff: The Strategic Partner Who Will Revolutionise Your Organisation” outlines criteria to consider when thinking of whether to hire a CoS, such as business size (medium to large is preferred); multiple, diverse lines of business; geographically dispersed teams; spin-offs etc.

While these apply best to the corporate CoS, Parris’s categorisation of organisation types that will best support healthy performance is helpful as a corrective to the idea of a fix-all hire for any type of business.

3. You need to sort out your management team or internal politics

As one CoS I spoke to asked, “are you hiring a Chief of Staff to hide the inadequacies of your management team?”.

CEOs should ask themselves whether they are looking for someone to support them in thinking broadly and strategically, focusing on the areas no one else has the time or capacity to, or whether they are hiring a sticking-plaster to patch over the cracks in their management team or extant culture.

A clear warning sign is if you’re looking to hire a Chief of Staff before making key C-suite appointments (or making the right appointments), expecting that individual to own the work of various departments or plug pre-existing gaps

More broadly, a CEO should consider whether political or cultural factors are blocking progress — is a lack of a CoS the issue, or is there a culture problem? And would their progress be blocked by factionality or internal power struggles from day one?

Similarly, would it be better to think about how your key leaders operate and report to you, rather than trying to bring someone in as a quasi mediator to wave the organisational wand and fix all your problems?

4. You actually need an Executive Assistant

Indeed, while there is considerable overlap between the two roles, it is worth considering whether you might be better served hiring an EA.

Generally, Executive Assistants are focused on the here and now — tackling immediate or short term concerns, that while no less important, are driven by the demands of the day and week.

By comparison, a Chief of Staff should focus on the long term n, concentrating on future planning and projects to ensure the growth of the organisation and the success of the CEO.

As one CoS I spoke to put it, “EAs are there to optimise their Executive to 100%, while a Chief of Staff exists to double this capacity”.

If you want an empowered individual to triage requests, handle a high volume of inbound, act as your personal gatekeeper and work to an urgent schedule, perhaps an Executive Assistant is instead what you need.

5. You expect the Chief of Staff to fully own functions, departments or products

One CoS I spoke with had spent the past nine months owning two internal business units in the absence of CxOs for these areas.

While they admitted that they had learned an impressive amount as an interim double-CxO, they were frustrated at their inability to devote proper time to tackling strategic questions and working directly with their CEO.

In fact, every CoS I spoke to noted the difficulty in not getting overly sucked into departments or products on an ongoing basis.

While a Chief of Staff is undoubtedly a useful tool to help take on those problems that no one else has the time to deal with, they should not become a “Chief of Stuff” owning everything that falls outside of someone’s specific remit, as this is a surefire way to bog them down and hamper their ability to think and work more expansively.

6. You’re not willing to delegate, and don’t want someone who will disagree with you

“It is crucial to understand how the other person thinks and works in order to work together efficiently and effectively. There can be growing pains here and there but the time spent up-front will come back to you both in spades down the line.” — Emma Ainley, Chief of Staff at 500px

Given their unique position outside of the formal hierarchy, a Chief of Staff should be empowered to step in on behalf of the CEO where necessary, freeing up their time to focus on overarching strategic concerns.

If the relationship between CEO and CoS functions well, it can be incredibly powerful, affording the CEO a stand-in who represents their interests and can coordinate processes on their behalf.

However, if a CEO is not ready to delegate this authority, or give up direct, constant control of processes or functions, the Chief of Staff is not set up for success.

Similarly, if a CEO isn’t ready to have a sparring partner that can speak truth to power, operating not just as an operational support but also a strategic sounding board, the relationship will never work.

If you’re not ready to delegate responsibility or prepared for healthy disagreement, maybe this isn’t the right hire for you?

7. You don’t have an idea of how this role will evolve

Lastly, any CEO looking to hire a Chief of Staff should have a sense of how this role can evolve, and where the individual can move to, once their two to three year tenure is complete.

The CoS role is unique in that it doesn’t exist within a formal hierarchy, and so has no direct next step. Given the ambitious nature of most CoS’s however, this “where next?” question should be one that is considered from the get-go.

The traditional routes out of the role include into senior Operations or Strategy positions, the C-suite of a smaller organisation, another CoS role elsewhere or with the Chief of Staff becoming a CEO or founder in their own right.

To ensure the longevity of the position, consider discussing with any inbound Chief of Staff where they see the role going, and where you as a leader could see them progressing. Covering this regularly in reviews or feedback sessions will ensure there is overlap in your ambitions as the role matures.

—

Please do let me know if you disagree, or believe I’ve missed any key points in the comments.

Big thanks to Matt Penney (Milltown Partners) for the much needed editing.

Further Reading:

• Harvard Business Review — The Case For a Chief of Staff
• Richard McLean (Medium) — Do You Want To Know About The Chief of Staff Role
• Washington Post — Silicon Valley Firms Are Increasingly Hiring Chiefs of Staff
• The Founder & The Force Multiplier — What Is The Difference Between an Executive Assistant and a Chief of Staff?
• Forbes — Are You Ready To Become a Chief of Staff?
• Brian Rumao (LinkedIn Learning) — Becoming a Chief of Staff
• Emma Ainley (Medium) — What it Means To Be a Chief of Staff at an a16z Start-up
• McKinsey & Company — The Mindset and Practices of Excellent CEOs
• Prime Advice — The Six Key Functions of an Effective Chief of Staff
• Bridgespan — What Is a Chief of Staff and When Do You Need One?
• Tyler Parris — Chief of Staff: The Strategic Partner Who Will Revolutionise Your Organisation
• Chris Whipple — The Gatekeepers: How the White House Chiefs of Staff Define Every Presidency