As an Executive Assistant, you are the trusted right hand to a leader. You manage chaos, anticipate needs before they arise, and act as the central nervous system for your executive’s world. You’re a master of logistics, communication, and getting things done. But have you ever found yourself thinking beyond the calendar and inbox? Have you started to see the bigger picture, connecting the dots between meetings and projects, and thought, "I can help drive the strategy here"? If so, you might be ready for a Chief of Staff role. This transition is a natural evolution for a top-tier EA. It’s about leveraging your unique access and operational skills to become a strategic partner who amplifies the leader’s vision and effectiveness across the entire organization. This article will show you how to turn your EA expertise into a launchpad for a successful career as a Chief of Staff.
Understanding the Chief of Staff Mandate
First, let's clarify what a Chief of Staff (CoS) actually is, because the role can look different from one company to another. At its core, a Chief of Staff is a strategic force multiplier for a leader. While an EA manages the executive's time and logistics, a CoS manages the flow of information and decision-making for the executive's office. They ensure the leader is focused on the most important priorities by taking ownership of special projects, facilitating communication between departments, and preparing for key meetings. Think of it this way: if the executive is the pilot of the plane, the EA is the air traffic controller for their schedule. The Chief of Staff is the co-pilot, helping to navigate, manage the instruments, and ensure the entire flight plan is on track.
Shift from Gatekeeper to Orchestrator
As an EA, a key part of your job is being a gatekeeper, protecting your executive's time and focus. As a Chief of Staff, your role evolves into being an orchestrator. You are no longer just guarding the door; you are conducting the orchestra of leaders and teams who need to work together. This means not just managing who gets on the calendar, but ensuring that when they do, the meeting is productive. You’ll be responsible for preparing briefing materials, defining meeting objectives, and making sure all follow-up actions are tracked and completed. It’s a shift from managing access to managing outcomes.
Develop Your Strategic Thinking Muscle
Strategy can feel like a big, intimidating word, but you can start practicing it today. A simple way to begin is by understanding your company's goals, often framed as Objectives and Key Results (OKRs). Objectives are what the company wants to achieve, and Key Results are how they’ll measure success. Ask your executive to share these with you. Once you understand the top priorities, you can start connecting your daily work back to them. When you schedule a meeting, ask yourself, "Which company objective does this support?" This simple question starts to build your strategic muscle and helps you see the "why" behind the "what."
Strengthen Your Cross-Functional Influence
A Chief of Staff has to work with leaders from every department, from marketing to engineering to finance. You need to be able to influence people who don't report to you. You can start building this skill right now. Instead of just being a name in an email, build real relationships with the key players on other teams. Grab a virtual coffee with the project manager from engineering. When you need something from the marketing team, pick up the phone instead of just sending a message. By building a network of allies and being known as a helpful collaborator, you build the foundation for the cross-functional influence you’ll need as a CoS.
Master Executive Communications and Board Materials
You are already a great communicator, but the CoS role requires a step up. You will likely be responsible for drafting company-wide announcements, preparing talking points for your leader, and even helping to create presentations for the board of directors. Start paying close attention to your executive's communication style. How do they frame a message? What words do they use? Volunteer to draft internal communications or help prepare the first draft of a presentation. This is a safe way to practice and get feedback directly from the source. Learning to communicate in your leader’s voice is a critical skill.
Learn the Basics of Project and Program Management
Many of a Chief of Staff's responsibilities are essentially special projects. This could be anything from planning an executive offsite to managing the rollout of a new company-wide initiative. You need to know how to take a big, messy idea and turn it into a structured plan. Learn the basics of project management. This doesn't mean you need a formal certification, but you should understand how to define a project's scope, create a timeline with key milestones, and identify who is responsible for each task. Start by applying these principles to smaller projects you already manage.
Learn to Read the Business with Finance 101
To be a true strategic partner, you need to understand the financial health of the business. You don't have to become an accountant, but you should learn to read the three main financial statements: the Profit and Loss (P&L) statement, the balance sheet, and the cash flow statement. Ask the finance team if they can give you a simple tutorial. Understanding these documents helps you grasp what drives revenue, what the company's biggest costs are, and how decisions impact the bottom line. This financial literacy allows you to contribute to conversations on a whole new level.
Build Your Decision-Support Toolkit
A Chief of Staff helps a leader make better, faster decisions. You can start doing this by creating simple "decision-support tools." For example, before your executive has to make a choice between two options, you can prepare a simple one-page document that outlines the pros and cons of each. Or, if a team is presenting a proposal, you can work with them beforehand to make sure their presentation clearly answers the key questions your executive will have. By preparing and structuring information, you save your leader mental energy and help them make a more informed decision.
Navigate Politics with Unshakable Integrity
The Chief of Staff role is inherently political because you operate at the intersection of power and information. The key to navigating this is to build a reputation for absolute integrity. Be discreet, be trustworthy, and always focus on what is best for the company, not what benefits one individual or department. Avoid gossip and be a neutral and objective source of truth. Your ability to be trusted by everyone, from the most junior employee to the board members, is your most valuable currency.
Find Your Mentors and Sponsors
You can't make this journey alone. You need mentors who can give you advice and sponsors who will advocate for you. Your current executive is your most important potential sponsor. Have an open conversation with them about your career goals. Show them you are committed to growing and ask for their support. Seek out a mentor who is a current or former Chief of Staff. They can provide invaluable guidance on the nuances of the role and help you identify the specific skills you need to develop.
Prepare for the Interview and Your Portfolio
When you interview for a Chief of Staff role, they will want to see proof of your strategic capabilities. You need to prepare a "portfolio" of your accomplishments. This isn't a design portfolio, but a collection of stories and examples. Be ready to talk about a time you managed a complex project, a time you improved a process that saved time or money, or a time you drafted a communication on behalf of your leader. Use the STAR method (Situation, Task, Action, Result) to structure your answers and show the impact you had.
Your First 90-Day Plan as a Chief of Staff
Once you land the role, your first three months are critical. Spend the first 30 days in "listen and learn" mode. Meet with all the key leaders your executive works with. Your goal is to understand their priorities, their challenges, and how they see the business. In your second month, identify and tackle one or two "early wins." These should be visible problems that are frustrating people but are relatively easy to fix. This builds credibility and shows you can deliver results. By day 90, you should be fully integrated, managing the rhythm of the executive office, and starting to take ownership of your first major strategic project.
