How to Transition from Executive Assistant to Chief of Staff

I’m quite vocal about my years as an Executive Assistant and now Chief of Staff, and therefore I often get asked how to transition from one position to the other. I, in turn, always answer that question with a question: “Why? Why do you want to move from an Executive Assistant to a Chief of Staff role?” The answers vary and all are valid. From recognition to compensation to more alignment to career growth and satisfaction. If you are thinking about making the transition from an Executive Assistant to Chief of Staff, here are some essential things you’ll want to consider before you make the move.

Let’s clear up a few misconceptions about the Chief of Staff role:

Chiefs of Staff do not necessarily earn more than Executive Assistants.

They can, but it often depends on the organization and the principal. For example, an EA to a celebrity or multi-passionate entrepreneur could very well earn more than a Chief at a non-profit or start-up. Bottom line, if you are looking to move from one position to the other, make sure it’s not just about the money. If you love your role as EA, but are looking to increase your compensation, there are ways to do that and still remain in the EA role (add more value to the company and ask for a raise, make a lateral move to another organization, update your job description and ask for compensation commensurate with your responsibilities, start supporting a different principal in your current company, etc.). Learn more about the Chief of Staff role here.

The next career step after Executive Assistant is not always Chief of Staff.

Sometimes it seems like becoming a Chief is the next logical career move for an EA. It’s not. It’s one career option; however, it’s just one, among many others. And, let’s not forget that being an Executive Assistant is an incredible career in its own right!

An Executive Assistant and Chief of Staff are not simply the same role with two different titles.

In some organizations, yes, the titles and positions are interchangeable; however, when we are talking about two distinct positions, the work is actually quite different. Someone looking to move from one role to the other would really need to understand their own natural behavior, as well as their long-term career goals, before pursuing a Chief of Staff positions. Read more about the differences between the two positions here.

How to determine if the Chief of Staff role is the right next career move for you:

First, determine what you’re willing to do.

The Chief of Staff role is more than a sexy title. If you are determined to move down that career path (and it’s a great one!), you may have to make sacrifices. You might have less personal time (or none at all), you will have increased pressure and responsibility, your commitment to your principal and career will be tested, you may take a pay cut, you may have to move to a different company or a new city. Be honest with yourself and what you are willing to do for your career (whether that’s an EA or Chief of Staff position) and then make peace with the answer.

Next, decide if it’s a compensation issue.

Oftentimes, EAs want to move to a Chief of Staff role because they believe their compensation will increase. As I mentioned above, that’s not always the case. No matter the title, this is always a tough, but important, conversation to be had. If you are not being fairly compensated for the work you are doing, gather your information, data, and results, and propose a compensation adjustment.

Lastly, do your research.

Before moving into a Chief of Staff position, I did extensive research about various C-Suite career opportunities, coaching and consulting roles, and other leadership positions. I eventually narrowed down my career goals to COO or Chief of Staff. After further research, it was clear the Chief of Staff role was not only where I wanted to grow in my career, it was largely what I was already doing. That may not be the case for you. Perhaps your next move is COO, or VP of Business Development, or Director of Public Relations, or Executive Director of a non-profit, or Executive Assistant in another industry. Consider all of your options and choose accordingly. Our newsletter is an excellent resource.

Next Steps for Transitioning from Executive Assistant to Chief of Staff

Now, after you’ve done some self-reflection and really dug deep into the question of why you want to become Chief of Staff, do you still have your sights set on the role? Great! Here are some next steps:

1. Determine what industry knowledge & skills you need.

When EAs are thinking about moving into a Chief of Staff role, I always encourage them to increase their knowledge base about the industry they want to serve in. A big part of being a Chief is not necessarily being an expert in one particular area of business, but rather having a broad knowledge of all parts of the business, and understanding the people that make that business function so they can guide decision-makers. I would also encourage anyone looking to become a Chief of Staff to hone their communication, leadership, conflict management, change management, and decision-making skills. Those are critical to master in order to be successful in this role. 

2. Talk to your leadership team.

Does this opportunity exist in your current company? Would it be a newly created role for the CEO or another principal in the organization? Or perhaps you want to start working towards replacing the current Chief when her transformational tour of duty is over? Who would replace you as Executive Assistant? Do you simply want a different title and additional responsibilities, but will keep your EA responsibilities as well? Determine what you want and then have the conversation. There is nothing wrong with promoting yourself (like I did) if the organization can support it.

Many organizations don’t need both an EA and a Chief of Staff. Often a Chief of Staff role will emerge when there is a Founder with multiple businesses, or when the organization is incredibly complex with various internal and external stakeholders, or if there is a principal who wants more day-to-day strategic support, or if a large organization is looking to develop junior leaders for future C-Suite positions. Does this sound like your company? If so, and a Chief role does not exist, this is a great opportunity to have that conversation with leadership and present this new role, which, naturally, you will fill.

3. Start looking at other companies.

If the opportunity to move from Executive Assistant to Chief of Staff does not exist in your current organization, it’s time to start looking elsewhere. Freshen up your resume, take any necessary professional development courses, start networking (hopefully this is an ongoing activity), and start interviewing. A natural transition could be in an industry you are already familiar with. Founders, family enterprises, and start-ups are also great targets. Any rapidly growing organization with multiple business divisions would benefit from a Chief. There are also several virtual Chief of Staff options.

4. Who do you need to become?

This role is constantly changing and often high stakes. It is a leadership position that flexes between strategy and execution and covers everything in between. You must be highly adaptable, influential, and organized. Study other successful Chiefs of Staff. What types of education or certifications have helped them in their roles? How are they showing up each day? What are their personal and professional growth plans? What books are they reading? The more you can learn from those who have gone before, the faster you will be able to provide value when you move into that role.

Are you ready to become a Chief of Staff? What do you still need to learn or change to make that move? Have you successfully made the transition? What did you learn?

Original post shared on November 20, 2021. Updated for 2024.

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