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The Chief of Staff Role Is Not a Promotion from EA
The admin world is full of people saying "Chief of Staff is the natural next step for experienced EAs." It sounds logical. You're already close to the executive. You already understand the business. You already coordinate, communicate, and keep everything running. So the Chief of Staff role must just be... more of that, with a better title. Right?
No. Not really.
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The Chief of Staff role shares some DNA with the EA role, but it is a fundamentally different job. Different scope. Different accountability. Different pressure. Different skill set. Calling it a "natural next step" does a disservice to both roles, because it implies the EA role is somehow a stepping stone rather than a career in its own right, and it dramatically understates what the Chief of Staff role actually demands.
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If you're considering this move, you deserve an honest picture of what's involved, not a motivational speech.
Two Roles. Same Universe. Different Planet.
An Executive Assistant makes the executive effective. A Chief of Staff makes the organisation effective. That distinction sounds small, but it changes everything about the day-to-day.
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Accountability is different. As an EA, you're accountable for how smoothly things run around your executive, their schedule, their communications, their workflow. As a Chief of Staff, you're accountable for whether strategic initiatives actually get delivered. You own outcomes, not logistics. When a cross-functional project stalls, that's your problem to solve. When a leadership decision isn't being implemented, you're the one who has to make it happen.
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The relationship with your executive changes. An EA supports their executive. A Chief of Staff challenges them. You're expected to push back on priorities, question assumptions, present data that contradicts what the executive wants to hear, and have difficult conversations about what's working and what isn't. If you've spent years building a relationship based on making your executive's life easier, shifting to a role where you sometimes make it harder is a genuine adjustment.
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Visibility is different. Much of the best EA work is invisible, that's often the point. A Chief of Staff can't be invisible. You're representing the executive in meetings. You're leading projects in front of the leadership team. You're making decisions that other people will scrutinise. If you're someone who thrives behind the scenes, this shift in visibility can feel deeply uncomfortable.
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The politics are different. As an EA, you navigate politics to protect your executive and get things done quietly. As a Chief of Staff, you're in the politics, you're mediating between senior leaders, you're making calls about resource allocation, you're the person people lobby when they want something from your executive. It's a completely different kind of political exposure.
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None of this means the EA role is "less than." They are different jobs. One is not better than the other. But they are not the same job with a different title.
The Skills That Do Cross Over (and the Ones That Don't)
Let's be specific about what your EA experience gives you and where the gaps are.
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What transfers well
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Stakeholder awareness. You already know how to read people, anticipate reactions, and navigate different communication styles. This is genuinely valuable in a Chief of Staff role, you'll just be applying it in a more visible, higher-stakes context.
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Organisational knowledge. Nobody understands the internal dynamics of a company like an experienced EA. You know who actually makes decisions, how things really get done, and where the bodies are buried. This institutional knowledge is an enormous advantage.
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Discretion and judgement. You've spent years handling sensitive information and making calls about what to escalate and what to handle quietly. Chiefs of Staff need this same calibre of judgement, though the decisions get bigger and the consequences get sharper.
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Communication skills. Clear writing, concise briefings, knowing your audience, these transfer directly. You've been doing this for years.
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What doesn't transfer
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Execution vs. strategy. Being brilliant at executing tasks doesn't automatically make you brilliant at setting strategy. A Chief of Staff needs to think about why the organisation is pursuing certain goals, whether those goals are right, and how to sequence complex initiatives across multiple teams. This is a different kind of thinking than even the most strategic EA work.
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Supporting vs. leading. An EA's strength is often in enabling someone else to lead. A Chief of Staff has to lead directly, running meetings, driving accountability, making decisions when the executive isn't available, and being the person other people look to for direction. If you've never been in that position, it takes practice.
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Project coordination vs. project ownership. Coordinating a project (tracking progress, scheduling check-ins, chasing deliverables) is different from owning a project (defining scope, managing risk, holding other senior people accountable for their commitments, and being responsible when it fails). The ownership piece is what catches most people off guard.
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Data and analysis. Most EA roles don't require deep analytical work — building business cases, interpreting financial data, creating dashboards, or making data-driven recommendations. Chiefs of Staff are increasingly expected to do this fluently.
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→ Take the Connected Leader Assessment to map your current skills
Is This Actually What You Want?
Before you start planning the transition, it's worth asking yourself some honest questions. The Chief of Staff role is not for everyone, and choosing to stay and grow as an EA is a completely legitimate decision, not a consolation prize.
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Do you actually want to lead, or do you want to be recognised? Sometimes the desire to become a Chief of Staff is really about wanting acknowledgement for the strategic work you're already doing. That's valid, but there might be ways to get that recognition without changing your entire role. A title change, a scope expansion, or a conversation about your contribution might be what you actually need.
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Are you comfortable with conflict? Chiefs of Staff spend a lot of time in uncomfortable conversations, pushing back on executives, mediating between leaders who disagree, delivering messages people don't want to hear. If you find conflict draining rather than energising, this role will wear you down.
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Do you want to be visible? The Chief of Staff role puts you in the spotlight. Your decisions get questioned. Your recommendations get challenged. Your mistakes are public. If you do your best work when nobody's watching, think carefully about whether this level of visibility suits you.
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Can you let go of the EA identity? This sounds small but it's real. Many experienced EAs have built their professional identity around being the person who holds everything together, who anticipates needs, who makes things seamless. The Chief of Staff role requires you to let go of some of that, to be comfortable with things being messier, with delegating the details, and with not being the person who always has the answer.
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If you're reading these questions and thinking "yes, I want all of that", then this might genuinely be the right move. If you're reading them and feeling uncertain, that's worth exploring before you commit.
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→ Discover Your Core Values - this helps clarify what actually drives you
Making the Move
What It Actually Takes
If you've thought it through and you're genuinely drawn to the Chief of Staff role, here's what the transition requires. It's not a quick pivot, it's a deliberate process that typically takes months of preparation.
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Build the skills you're missing. Be honest about the gaps. If you've never led a cross-functional project end to end, find a way to do that, volunteer for one, propose one, create the opportunity. If your data skills are thin, invest in building them. If you've never had to present a strategic recommendation to a leadership team, start practising. The skills gap is the most concrete obstacle, and it's the one you have the most control over.
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Start doing the work before you have the title. This is the one piece of advice that's the same for any career transition: demonstrate that you can do the job before anyone takes the risk of giving it to you. Take on projects that stretch beyond your current scope. Offer to prepare strategic briefings, not just meeting agendas. When asked for your opinion, give a recommendation with reasoning, not just options.
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Make your contributions visible. If you're already doing strategic work that nobody sees, that needs to change. Share what you're working on. Present in leadership meetings. Make sure the right people understand the value you're adding. This isn't about self-promotion, it's about making the case that this role change would formalise something that's already happening.
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Have the conversation. At some point, you need to talk to your executive directly about what you want. Frame it around value: you're not asking for a favour, you're proposing a structure that lets you contribute more effectively. And be prepared for the possibility that the answer is "not here", some organisations don't have a Chief of Staff role and won't create one, no matter how good your case is.
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Be realistic about the timeline. This isn't a three-month project. Depending on where you're starting and what your organisation looks like, the transition could take six months to a year of deliberate positioning. And it might ultimately mean moving to a different company where the role already exists.
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→ Clarity Sprint — work through this decision with structured coaching
The Case for Staying and Growing as an EA
Here's something nobody says often enough: staying in the EA role and getting really, really good at it is a perfectly valid career choice. Not a backup plan. Not settling. A choice.
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The best Executive Assistants in the world are extraordinarily skilled professionals. They're trusted advisors. They shape decisions. They're paid well. They're respected. The role has more upward potential than most people realise, but capturing that potential requires the same kind of intentional development that a Chief of Staff transition would.
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If what you actually want is more recognition, more strategic involvement, more influence, and a better title, there may be ways to get all of that within the EA career path. Before you commit to a Chief of Staff transition, make sure you're not solving the wrong problem.
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→ Take the Irreplaceable Audit — understand your real value in your current role