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As recently as our last send, I highlighted the difference of opinion on whether the City of London is safe. The TL;DR was that many segments of the population thought London was unsafe. Those who disagreed the hardest were the people who actually live in London. In the last day or two, I found the receipts.

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So, What Does A Chief Of Staff Actually Do

I had a wonderful chief of staff at my startup, Athyna, until she was promoted out from under me. You will hear from her as you read on. We did great work together. But I’ll be honest, even I don’t know what a chief of staff really does, or rather, what they should do? I assume you feel the same or similar.

Today, we sit down with a handful of chiefs of staff (or is it chief of staffs) to understand what exactly they do do. And we are bringing some data to add some layers to this salty but sweet, operational sponge cake.

Before we dive in and talk about the most mysterious role in technology, let’s take a quick quiz to see who in today’s tech landscape operates with—or has operated with in the past—a chief of staff.

Historical backdrop & evolution

Today, the chief of staff may seem like the hottest new trend. A spicy title to hand to someone coming up through the ranks. However, it is not a new trend. The role has a long, illustrious military history.

The image below depicts Napoleon and his chief of staff at the time, Marshal Berthier. While Napoleon and the Grande Armée were out fucking shit up—excuse the French—all across Europe, Berthier was working away on very little sleep, setting things up, so Napoleon could come in and knock them down. It was a match made in imperialist heaven.

The role was next adopted by two recent military powerhouses—Germany and Britain—but to very different effect. Germany, following the Prussian system from the early 1800s, used the role to employ strategic leaders who would serve as close counsel to the general, with the potential to command independently when necessary.

The Brits, on the other hand, introduced the role in 1905, but it was more of an organizational figure, serving as a liaison between officers and the front line. We will explore the different levels of today’s chiefs shortly.

First chiefs in business

Following its rise in the military, the title ‘chief of staff’ has gained traction in corporate settings over the last few decades as businesses recognised the value of a senior leader responsible for aligning strategy and operations. Very similar to its original function in government and the military.

Terrence Holt is one of the first examples, serving PepsiCo's CEO in the early 1990s (remember when soda was cool). This was one of the first high-profile chief of staff roles in a large corporation. Jeanne Holm is another, serving as the President and COO of Dell in the late 1990s and playing a significant role in the company's success.

There are others that you could say played roles like a chief of staff, like John Doerr, of Kleiner Perkins fame, to Intel’s Andy Grove in the 80’s, and Jony Ive to Steve Jobs in the 90’s, and Sheryl Sandberg to the The Zuck. But the best example of all is Ann Hiatt.

Ann Hiatt went from executive business partner (let’s call it CoS) to Bezos, then straight into the chief of staff role for Google's founder, Eric Schmidt, for a leisurely 12 years.

Key functions of a chief of staff

Before moving forward, I’d like to take a moment to introduce those who were kind enough to donate their time to help flesh out the experience of a chief of staff today.

Launching partnerships, managing product integrations, people, culture, hiring, and more. Katie Noonan cited planning meetings, investor relations, partnerships, culture, and special projects as part of her day-to-day.

I also loved reading about the typical day of Albert Patajo. Incredibly varied, random, but also important.

My chief of staff at Athyna, Bea, manages many of our goals, OKRs, and accountability, as well as documentation and organisational design.

The overall theme I noticed in researching this piece is that the chief of staff is the chief problemo solver. Aside from some organisational rituals, the day-to-day was incredibly varied across the board. One thing was certain, though: they were always working on the biggest projects and initiatives.

Next up, we will look at how each of our Chiefs approaches freeing up the cerebral horsepower of the leaders they work with.

How to find leverage

The idea of finding more leverage as a CEO is simple. You want to ensure you can always focus on the most important things. Let’s look closely again at how our CoSs think here. Starting with one answer in our anonymised section.

Jo Robyn, our only VC respondent, said the following: “I see it as my number one goal to create leverage for our partners' time - that is measured by taking things off their plate and owning respective parts of the business that they were previously owning.” 

And Max Kausman, when asked his priorities, followed up similarly: “Founders' time saved: the ability of the founders to work in their 'zone of genius' rather than time they're required to spend on other topics.” A definite thread here.

_{*Note: The following tweet does not really fit this section, but it’s too good to push too far down this piece. Sorry, not sorry.}

When thinking about leverage, though, I think the best summary came from Belen Wagaw, who spent two years at SAP and later became the head of a 19,000-person division.

If you are a leader reading this—but are not sure what you would do with additional time—think of what your personal zone of genius is. What handful of things are you really good at, really enjoy, and/or will make the most impact for the organisation?

For me, it’s communications. I believe strategy, financing, hiring, communications, and accountability are the five keys to my role as CEO. Thanks to my ‘Office of the CEO’, namely my chief of staff and content assistant (EA, but for content), I can produce 3-4x the communications in half the time.

I believe I am building a leadership brand that will be a huge driver of our organisation over the long run. So what is it for you? What is your zone of genius?

Levels to the game

One of the most helpful frameworks I found came from Harvard Business Review, which broke the chief of staff role into three levels. Let me summarise them for you.

Level 1 - Apprentice Padawan

At the first level of the role, someone is coming through the EA path and is ready to take on more responsibility within the organisation and with the leader. Typical tasks may include preparing pre-work, handling follow-ups, and attending most board meetings.

Level 2 - Mentat

The next level of CoS is the Mentat—someone who, when called upon, can add true strategic value and implement on the CEO’s behalf. This role might be suited to someone coming through an MBA path, possibly in management consulting.

Level 3 - Hand of the King

The third and final level is graduation to the King’s (or Queen’s) Hand. In this situation—if you can avoid getting your head lopped off—you are expected to sit directly astride the CEO. Here, you may have come from a decade as an exec or department head inside of big tech or another big enterprise org.

For what it’s worth, my chief of staff, Bea, is probably somewhere in between a Mentat and the King’s Hand. She helps me execute on major projects inside of Athyna, coordinates all of our goals-setting and OKRs and is the first person to often push-back on me related to cultural, operational and legal areas inside of the business.

She has no reports, spends one hour with me every Monday to set our goals, and came up through the ranks with us first as our legal advisor. Her background is employment law.

Is a chief of staff an executive?

One of the questions commonly asked is where they sit within an organisation's hierarchy. Are they a department head level, a true exec, a glorified assistant? I don’t think there's a right or wrong answer here; it largely depends on your CoS level, your organisation's maturity, and your overall philosophy.

I don’t know how much credence to give GitLab’s scale, however, because they think the numerical system we use starts at four and also don’t believe in the number 13. Do your own research here.

One final thought on where the role sits is where our batch of 10 from our research believe they will land in the next role.

It’s a very small sample size, but 50% of our respondents expect to be a CEO, C-suite executive, or general manager in their next role. With a further 20% expecting to become a VP or department head.

A handy resource

While preparing for this piece, I also spoke with Cedar CEO Mackenzie Lee about how he views the chief of staff role. Mackenzie and Cedar know a thing or two about the role. They actually find chiefs of staff for large enterprises such as Barclays, Citi, Stanford, and more.

One of the better resources I found in my research was Cedar’s 44-page chief of staff Playbook. I hope you find this useful as well.

When and how to hire a chief of staff

So you want to hire a Chief of Staff, but don’t know where to start. This is how I’d go about it from idea to onboarding.

• Identify need: Is your calendar constantly overflowing? Do you need someone to share the operational load? Are you feeling like you are not able to spend the time executing on what you need to execute on—great, you need a CoS.

• Decide on experience level: Not every company needs a Hand of the King. Sometimes, if you are a small scrappy startup, you might be looking for your Anakin—an L1 entry-level talent. Not all CoS are made equal.

• Create your ideal candidate profile: Just like the ICP for revenue-driven activities. Who are they, what is their background, what skills should they have, and what can they take off your plate? Detail matters.

• Decide on hiring strategy: This part is important. Not every candidate will come externally. You may have an EA, product hire, sales rep, etc., who wants to do the job. Someone with consulting or operations experience is going to be well-suited, but someone who is polished and works hard inside of your org may want to take on the challenge.

• Recruit and vet: The fun stuff happens here. Recruit, recruit, recruit until you have found the right fit—or at least the thing you have. Then put them through some on-the-job testing. Try to see how they execute and how they think.

• Document, onboard, and handoff: And finally, get all the things you want taken care of documented so as soon as your new CoS is onboarded, you can hand them off. Voila, you have a Chief of Staff.

💡 Note: If you are looking to hire an EA, Chief of Staff, or any other remote role for that matter, my startup, Athyna, can help.

Future

In today’s tech landscape, the chief of staff is going from strength to strength. A study in February 2023 found 4,700 roles in US organisations. I am increasingly seeing that not only does a CEO have a chief of staff, but we are also seeing the same across the chief product officer, a CRO, and more.

Not only that, but we are also beginning to see a growing trend toward establishing an Office of the CEO. Chief of staff, deputy chief of staff, and an executive assistant (or two). The premise is that we want the executive to spend as much time as possible using their head, not their hands, and I, for one, am all for it.

BRAIN FOOD 🧠 

TWEETS OF THE WEEK 🐣 

TOOLS WE RECOMMEND 🛠️

Every week, we highlight tools we like and those we actually use inside our business and give them an honest review. Today, we are highlighting Vanta*—the security and compliance platform companies rely on to stay audit-ready without losing their sanity.

See the full set of tools we use inside of Athyna & Open Source CEO here.

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