I get asked about this more than almost anything else, and the question is usually the same underneath: is Chief of Staff the promotion?
It is a fair thing to wonder. The title sounds like the next rung. It often pays more. And after enough years of being introduced as "just the assistant," a job that comes with an obvious 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 are not two rungs on one ladder. They are two different jobs that happen to sit next to the same executive.
The difference is what you own, not how senior you are
The cleanest way I have 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 time, 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 is not yet ready for them.
Which is to say the difference is not seniority. It is the direction the job points. One is pointed at a person. The other is pointed at an organization.
Both jobs are strategic. Only one gets told so
Here is the part of this conversation I want to push back on, because it comes up in almost every episode.
The framing that "EA is tactical, chief of staff is strategic" is wrong, and it has done real damage to how assistants see themselves. I have met EAs who influence hiring, restructure how a leadership team runs, and quietly decide what does and does not reach a CEO. That is strategy. It is simply strategy that nobody put in a job description.
So if the reason Chief of Staff appeals to you is that you want strategic work, pause before you start applying. You may already be doing it. The thing you are actually short of might be the title, the pay, or the recognition — and those are worth going after directly, which is a different and often shorter conversation with your executive than a 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 are candid about the trade.
You lose the proximity. The EA seat is the closest one in the building. A chief of staff is often further out, running things at arm's length, and several people have described missing the shorthand that comes with sitting right next to someone all day.
You gain direct reports and everything that comes with them. Performance reviews, difficult conversations, someone else's development. 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.
The role is much less defined. An EA job is understood, even when it is undervalued. Chief of Staff means something different at every company — at one it is a chief operating officer in training, at another it is a glorified project manager, at a third it is essentially a senior EA with a better title. This is the single biggest thing to interrogate in an interview.
The ceiling may be lower than it looks. Chief of Staff is frequently a two-to-three-year role, a deliberate stepping stone to something else. That is fine if you want the something else. It is worth knowing going in if you do not.
Questions worth asking before you chase the title
If you are seriously considering it, these are the ones that have come up again and again:
- Who does this role report to, and who reports to it?
- What decisions can this person make without checking?
- What happens to the person in this role in three years — is there a named path, or is it a holding pattern?
- Is there still an EA supporting this executive? If not, be honest with yourself about how much of your week is going to be calendar work with a grander title on it.
- Why is the role open? A first-ever chief of staff and a fourth-in-five-years chief of staff are very different jobs.
And if you decide to stay
There is no shortage of people ready to tell assistants that the goal is to become something other than an assistant. I do not believe that, and I have spent close to four hundred episodes talking to people who prove otherwise.
Staying is a legitimate ambition. 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.
The conversations below cover both routes. Several of them are with people who went one way and several with people who went the other, which is the point: there is no single right answer here, only the one that fits what you actually want your working life to look like.