I get asked about this topic a lot.
Is chief of staff the next step for me as an executive assistant?
It's a fair thing to wonder. CoS could very well be the next rung on the EA career ladder. It often pays more. And after enough years of being introduced as "just the assistant," a job that comes with a "built in" seat at the table is appealing for reasons that have nothing to do with the work itself.
But I have now had this conversation on the podcast with dozens of people who have done one job, the other, or both – and the honest answer is that these roles aren't typically two rungs on one ladder. They're often two different jobs that happen to sit next to the same executive.
This guide is what I've taken from those conversations. If you'd rather hear it from someone who trains chiefs of staff for a living, start with Maggie Olson on what a chief of staff actually is, where she works through the differences between EA, CoS, COO and CEO. Every other episode I mention is linked as I go, and the full list can be found at the bottom of this page.
The difference is what you own, not how senior you are
The cleanest way I've heard it put is this: an executive assistant makes the executive effective. A chief of staff makes the executive's organization effective.
That sounds like a small distinction until you look at what lands on each desk.
An EA owns the executive's energy, attention and access. The calendar, the inbox, the travel, the relationships, the preparation, the follow-through. The work is judged by whether the executive can do their job well, and a great EA is often the only person in the building with a complete picture of what the executive is actually dealing with.
A chief of staff owns things the executive has delegated outward rather than inward. Running the leadership team's operating rhythm. Chasing a strategic initiative that has no other owner. Sitting in a meeting instead of the executive and making a call. Standing between the executive and a decision that isn't yet ready for them.
Which is to say the difference isn't seniority. It's the direction the job points. One points at a person. The other points at an organization.
Whitney Faires, who was chief of staff to a Fortune 500 CFO, is worth listening to on how those two jobs have been drifting in relation to each other – and on the core competencies that turn out to matter in both.
Side note: If you're reading this thinking, "Jeremy – I have an EA title, but my role sounds an awful lot like what you just said a CoS role is." Well, join the club! There are a lot of assistants in your shoes. On the flip side, there are chiefs of staff who are more like EAs when you look at what they do day in and day out.
The EA vs CoS distinctions are general and can vary industry to industry, and role to role. Speaking of…
The title means something different at every company
This is the single most important thing to understand before you start applying for the CoS title, and it's why so much online advice about the role contradicts itself.
At one company, chief of staff is a COO in training. At another it's a senior project manager for the executive's pet initiatives. At a third it's, honestly, a senior EA with a better title and no additional authority. All three are real, all three advertise under the same two words, and the job description won't always tell you which one you're looking at.
The range shows up clearly across the conversations I've featured on The Leader Assistant Podcast. Jared Blank at the University of Texas, Elise Kennedy in a family office, Cathy Rong for Questlove, and Concetta Green at Harvard Business Publishing all hold the same title and do noticeably different work. Cathy manages an artist's professional and personal life day to day. Jared works inside a large public university. Concetta describes diving head-first into ambiguity at a well-known brand.
If you want the widest possible version of this, Patrick Jephson was chief of staff to Princess Diana, which isn't a job any description would have prepared anyone for.
So when someone tells you what a chief of staff does, the useful follow-up is always: where?
Both jobs are strategic. Only one gets told so.
Here's the part of this conversation I want to push back on, because it comes up constantly and while it can be helpful in some cases, it's not so cut and dry.
The framing that "EA is tactical, CoS is strategic" has done damage to how assistants see themselves. I've met EAs who influence hiring, restructure how a leadership team runs, and quietly decide what does and doesn't reach a CEO. That's strategy. It's simply strategy that nobody put in a job description.
Listen to Ashley Langlais on supporting the goals of her CEO, or to the team supporting Microsoft Germany's CEO office, and try to find the line where the tactical work stops and the strategic work starts. It isn't there.
So if the reason CoS appeals to you is that you want strategic work, pause before you start applying. You may already be doing it. What you're actually short of might be the title, the pay, or the recognition – and each of those is worth going after directly. Sometimes that pursuit is a shorter and more winnable conversation with your executive than a whole role change.
What the move actually costs
The episodes where someone has made this move are the ones worth listening to most closely, because they're candid about the trade. Maggie Olson's episode on whether chief of staff is the next step for EAs is the one I point people to first, and her walk-through of how to level up covers the mechanics.
You lose the proximity. The EA seat is the closest one in the building. A CoS is often further out, running things at arm's length, and several people have described missing the shorthand that comes with sitting beside someone all day. If the part of your job you love is knowing your executive well enough to finish their sentences, think twice before trading that way.
You gain direct reports and everything that comes with them. Performance reviews, difficult conversations, someone else's development and someone else's bad week. Some people find that the best part of the job. Others discover they preferred being the person who makes things work to being the person who manages the people who make things work. Neither answer is a character flaw, but it's worth knowing which one is yours before you sign up for a CoS position that requires you to manage people.
You take on ambiguity as a permanent condition. An EA job has a shape, even when it's overloaded. A CoS role frequently doesn't, and the first six months can be spent working out what you're actually supposed to be doing. If you're someone who draws energy from bringing order to a mess, that's the appeal. If you need to know what good looks like before you can do good work, it's a genuine warning sign.
The ceiling may be lower than it looks. Chief of staff is often a 2-3 year role, a deliberate stepping stone to something else. That's fine if you want the something else, and worth knowing if you don't. Ask what happened to the last three people who held the position.
The pay isn't automatically better. It usually is. It isn't always, and a senior EA to a CEO at a large company can out-earn a CoS at a small one. Get real numbers before you let the title do your negotiating for you.
If you decide to go for it
A few things come up again and again from people who made the move successfully.
Business acumen is the gap that actually blocks people. Not project management, not communication – those most EAs already have. It's being able to read a P&L, follow a budget conversation, and understand how the company makes money. Maggie Olson's episode on building financial acumen in your role is the most practical thing I've published on closing that gap, and it's worth doing whether or not you ever change titles.
Your EA experience is an advantage, not something to apologize for. You already know the executive, the politics, the history and where the bodies are buried. An external hire spends a year learning what you know now. Several people have said the transition worked precisely because they weren't starting from zero on the relationships.
Get the relationship with the EA right from day one. If you become CoS and there's still an EA supporting your executive, how the two of you divide the work decides whether both jobs are set up for success. Maggie Olson has a step-by-step episode on exactly this relationship, and it's the one I'd send to anyone about to be on either side of it.
Talk to people doing the job. Clara Ma founded a network for precisely this, and a group of Nova graduates talk through what the training and the transition were actually like. Thirty minutes listening to someone doing the job at a company like yours is time well spent.
Questions worth asking before you chase the title
If you're seriously considering the move from EA to CoS, these questions are worth considering:
- Who does this role report to, and who reports to it?
- What decisions can this person make without checking first?
- Is there still an EA supporting this executive? If not, be honest with yourself about how much of your week will be calendar work with a grander title on it.
- What happens to the person in this role in three years – is there a named path, or is it a holding pattern?
- Why is the role open? A first-ever chief of staff and a fourth-in-five-years chief of staff are very different jobs.
- What does this executive think a chief of staff is for? If they can't answer crisply, you'll be answering it for them, in public, for a year.
And if you decide to stay
There's no shortage of people ready to tell assistants that the goal is to become something other than an assistant. I don't believe that, and I've spent close to four hundred episodes and over 10 years talking to people who prove otherwise.
Staying is a legitimate ambition. In fact, I've been an EA for 20 years and while I've often put on a CoS hat in my role, I don't have any desire to keep it on full time.
A senior EA to a CEO can out-earn, out-influence and out-last a chief of staff, and the path to that runs through getting better at this job rather than leaving it – deeper business acumen, a real partnership with your executive, and the confidence to say what you think in the room.
Leah Warwick and Maggie Olson on the state of the profession is a good conversation to check out on where the work is heading, and it isn't heading somewhere that makes this job smaller.
It's also worth saying that this isn't a one-way door. Cathy Rong was lead executive assistant at Complex Network when I first interviewed her and chief of staff to Questlove by the second conversation. People move between these jobs in both directions, and a few years in one makes you better at the other.
The conversations linked below cover both routes. Several are with people who went one way and several with people who went the other, which is the point: there's no single right answer here, only the one that fits what you actually want your working life to look like. No matter which direction you choose, keep leading well.