What it’s really like to be the Chief of Staff to a CEO
7 min read

What it’s really like to be the Chief of Staff to a CEO

We asked the Chief of Staff to the CEO at a large company for honest responses to our interview questions. They didn’t disappoint. Find out what they actually do, learn some industry secrets and get tips on how to succeed as a Chief of Staff.
What it’s really like to be the Chief of Staff to a CEO

What do you tell people you do?

I tell people that I work with the executive leadership team and CEO, focusing on the biggest strategic priorities that cut across everyone’s function. The priorities can be anything from growth to sales operations to regulation - but what they have in common is that they are initiatives that require every function to pull together to make them happen.

What do you really do?

I translate and I negotiate. Much of the time, “what” we need to do is clear, it’s the “how” that is the problem - aka execution. The complication comes from the fact that in a big multinational, every function has its own objectives and machinations. Different areas of the business struggle to understand each other's priorities and ways of thinking.

Enter the Chief of Staff - I “work” for the CEO but really I work for the whole leadership team. I have an objective view so I can remove myself from the situation and help each leader understand where the others are coming from when there is an issue (i.e. “the translator”). It might be that Legal has a different way of thinking about risk than Marketing, or that they literally have different directives from global, either way, they need help understanding each other if we are going to execute successfully. Once we get into a situation of common understanding, we need to work out how we make the right trade offs (i.e. “the negotiator”). My job is to help the CEO make sure that we get to the right outcome for the company, not any one function. This involves not just coming up with the answer, but understanding the implications for each function and working with the leaders to make sure they are all truly bought in.

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What is the biggest misconception about the role?

The biggest misconception is that you’re just the “doer” for the CEO. Of course, I spend a lot of time with the CEO, so when there is a situation that they don’t have capacity to manage, they will delegate it to me to handle it. But, what the label “doer” misses is the critical thinking and challenge that you need to bring to the CEO.

In the Chief of Staff role, you get to see situations play out from afar because you are not the head of any particular function. You have a more objective perspective that is unclouded by sometimes competing objectives of other leaders. This is a very valuable perspective for the CEO to have when they have to make trade-offs, manage team dynamics or land a difficult message.

Why do most people get into this role?

The people who end up in Chief of Staff roles are very diverse, mostly because every CEO is looking for something slightly different. Those I know of either come from a management consulting background or from communications (when they are mostly focused on speech writing and investor presentations etc).

Most people get into this role for the exposure to senior leaders. They are often too early in their career to be targeting a CEO-role themselves in the next 5 years, but know that working with the most senior leaders in a company will give them both good experience and good connections. When influential people have worked with you so closely, you’ve got a good chance at landing a good opportunity afterwards.

What three main skills do people need to bring to this role?

Reframing problems. When different leaders’ perspectives get lost in translation, that’s when conflict arises. People start talking over each other and past each other and it is hard to agree on a decision and then execute. Being able to “reframe” the problem at hand to bring everyone back to the beginning to explain their point of view is so important. You’re helping them drop their baggage at the door and focus on coming up with a solution together.

Relationship building. I think it's impossible to do this job without a great relationship with the whole leadership team, not just the CEO. Part of your value is your ability to read between the lines when the leadership team is interacting and proactively address issues before they become a problem for the CEO. This requires knowing everyone really well (what they aspire to, what they’re scared of, what irks them) and getting to know someone really well requires trust.

Getting people to do things they don’t want to do. In a perfect world, everything that was important would also be fun to do - it’s not. Sometimes what needs doing is tedious (think: status reports, board presentations with lots of detail). Being a Chief of Staff means making sure these critical (sometimes not exciting) things get done so that all the i’s are dotted and the t’s are crossed. It takes good program management paired with an ability to get others to pitch in (on time!) when you need them to.

What did you least expect in this role?

I didn’t expect how much influence I would have after only 6 months or so. In the first 6 months, most things I would run past my CEO - we would have a bit of a rapid fire session where they would quickly decide what we would focus on and what we would say “no” to. But, after that, I got such a good sense for what they would prioritize (and what they might usually say “yes” to but shouldn’t because it didn’t align to their ultimate goals) that I was confident making those calls without running them by them. This made us much more efficient and unburdened the CEO (which is the whole point), but it is a huge amount of influence to wield. You’re essentially filtering which requests even make it up to them, and putting those you think are most valuable at the top of their list.

I didn’t expect how much this influence would change my other relationships at the company, either. Rightly or wrongly, some people will see you as a gatekeeper to the CEO and you find yourself getting pitched ideas or resource requests as a way to get onto the CEO’s agenda.

What’s the most frustrating part of the role?

The lack of actual accountability. It’s so strange to be so close to the most critical issues in the company, but not actually directly accountable for the outcomes. Ultimately, that’s the CEO. After that, it’s the leaders of each of the functions. No one is questioning the Chief of Staff when you miss a revenue target or ended up in the paper for the wrong reason.

In a way, it’s freeing. You can be objective about what needs to be done without worrying about your own skin. What I’ve found, though, is that eventually you want to feel a bit more of a sense of ownership. Your failures will be your failures but the successes will be your own rather than something you contributed to.

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What would only other people who do your role know about it?

How many of the most senior leaders have incentives that just don’t align. Misaligned incentives are a nightmare for a Chief of Staff who is trying to drive consensus between a leadership team. Leaders are very good at putting up a united front and often genuinely want to work together towards a common goal. However, when you look at how they actually get paid and rewarded (think promotion opportunities, praise), it can pit them against each other. For example, the Head of Marketing is going to get all the accolades for driving record sales with a bold, edgy marketing campaign… but then you’ve got a Head of Legal that is incentivised to prevent any legal or PR Issues that might come from a bold new way of positioning your product. The Head of Legal gets no pats on the back for a record year of sales.

What would the haters say about this role?

What a lot of people see from the outside is project management. You’re often asking people for status updates to make sure that key initiatives are on track and any issues are spotted early so they don’t catch the CEO off-guard. This gives the impression that you’re some sort of project manager, but in reality, that’s just because it's just the tip of the iceberg that those outside of the leadership team can see.

What advice do you have for people considering this role?

Make sure you gel with the CEO. At some stage you are probably going to need to make some decisions on the CEO’s behalf. Having a great relationship is so important because (a) you need to be able to think like them and (b) you’re going to make mistakes and you need a strong enough relationship that little blips don’t fundamentally impact the trust between you. Personally, I’m at my best when I really care about the person I work for and I’m invested in their career - I don’t think I’d be as good at my job without that.

Know what you want to get out of it and be honest about it. I’m not suggesting you shout it from the rooftops as soon as you get the job but the CEO should know what you want to get out of the role and (when you work it out) what you want to do next. Not only can you then work together to make sure you’re getting the right experiences out of the role, but the CEO can be your greatest advocate and supporter to make it happen.

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