What Comes After the Chief of Staff Role?

As a Chief of Staff (CoS), you experience the professional life of a busy executive and the day-to-day operations and initiatives he or she oversees. Given the variety of your responsibilities and the versatility you possess, defining the right position after completing your CoS stint can be difficult. However, you should be able to use your laundry list of responsibilities, skills, experience, and accomplishments to position you for a number of subsequent positions. The good news is, you have options.

Staying with your current company in a leadership position


Of course, the CoS position already carries leadership weight. Choosing to stay with a company can be a common choice for a number of former CoS’s who feel embedded into the business, internal and external relationships, and ways of doing things. It is also a heavy favorite among executives who spent a great deal of time nurturing your growth and don’t want to see you leave.

If you choose to stay with your current employer, you might do so in a senior operations and/or strategy role because of the more comprehensive nature of these areas compared to others like legal or finance. Your CoS background provides the broader scope necessary for a more general management track that leads its way to a COO position, and potentially beyond. In my current role, I have seen people take Vice President (VP) or Chief Operating Officer (COO) titles, depending on level of experience.

Benefits: You already know the ins and outs of the company and are still within earshot of your executive and the rest of the leadership team.

Consequences: You may not fully relieve yourself of CoS duties and/or an unhealthy dependency between you and your executive. Establishing new boundaries is critical but can be difficult to do.

Leaving your current company for a non-chief of staff role


This is the most common scenario I see. There are two key reasons for this. First, the nature of the CoS role can cause burnout. This occurs not only within the role, but also within the company. The prospect of staying with the company might come with a host of strings attached and a stamp on your forehead saying, “eternal Chief of Staff.”

The second reason for a departure from the company is because once given exposure to the company’s operations, decision making, and strategic vision, you decide it is not the place you wish to continue your career long term. Maybe you’ve learned and gotten excited about new skills or interests, and there is no position for you doing that work. Or, as the company has evolved, you simply find that you are no longer in alignment with the vision and decision making above.

A majority of people who leave the company pursue positions like VP or higher in strategy or operations, VP or higher in corporate development, or Executive Director at nonprofit organizations. Leading a nonprofit may sound unusual, but nonprofits benefit from hiring business minds that understand the ins and outs of operations. A Chief of Staff with leadership aspirations is a great candidate for these organizations.

Benefits: A new company affords you the opportunity to cut the dependency cord with your former boss and chart new territories that may better suit your long-term career goals.

Consequences: The catch-22 of leaving your former boss: you no longer have that rapport and trust with an executive who champions your abilities and reputation. But don’t worry, you can build it again somewhere else.

Leaving your current company for another chief of staff role


Some people wish to continue riding the CoS train. You’ve found your niche role supporting executives and you have no ambitions to further climb the leadership ladder, at least not right now. That’s great, and kudos to you for finding a position you love where you truly excel. I see CoS’s decide to leave a current employer for similar positions elsewhere due to reasons like reductions in force, changes in the leadership team, relocations for personal reasons, or simple desire for a change.

Benefits: You already know the role so your learning curve should be significantly diminished. Employers are attracted to your previous experience supporting an executive—it gives them more comfort in hiring you for the job.

Consequences: Your boss may be offended by your decision to dump him or her for another. Also, this role has a time stamp at a number of organizations given its intensity and demands. Fewer people want to, or can, stay in the role for more than a few years. While there is a select group of folks who become career-long CoSs, the opportunity for burnout is high.

Starting your own gig


As you know, your role provides a unique lens into the management of a business through company leadership. Therefore, some former CoS’s venture out on their own—armed with more credibility and confidence to start and grow a business than before. Sometimes this new business is a direct result of identifying a new idea or solving a challenge at their former employer.

That was the case for me. However, it wasn’t simply enduring the CoS role that empowered me to start a business. It was also an entrepreneurial bug I’ve had since an early age. I started other companies and side projects in the past and learned from a number of failures before my most recent business attempt (and so far success). I say this to forewarn anyone considering going out on their own—it’s not easy and the CoS role isn’t an admission ticket to Entrepreneurial Successville.

Benefits: You have a clearer idea of the way you want to run your business and manage your employees by learning from someone else. You experienced failures working for a company, so you will hopefully not fall victim to some of those same pitfalls. You may also have the opportunity to bring on your former employer as a first client (this, of course, depends on what products/services you provide).

Consequences: As if you didn’t know, starting a business is hard. You may fail. However, if you do, you are still employable.