The Chief of Staff Guide — Part 4: Career Path

October 27th, 2018

This is the final article in a four-part series. In the previous article, I discussed strategies to mitigate the common pitfalls that Chiefs of Staff face.


There is no set career path for a Chief of Staff. Some take the role early in their career, others move into the role 5-10 years into their career (often post-MBA), while some take the role 15-20 years in, typically in larger organizations and as an adjunct responsibility (e.g., CFO & Chief of Staff). In this article, I’ll provide general recommendations for the first six months, discuss how the role can drive your professional development, provide illustrative profiles from several Chief of Staff friends, and offer suggestions on transitioning to your post-Chief of Staff role.


What to Do in Your First Six Months

In addition to the traditional 30/60/90 day onboarding advice (The First 90 Days is a good resource), I’ll provide a few additional recommendations.


1. Map the organization while building relationships

You will be working with almost everyone, and almost everyone will hear about you in some capacity, so it’s important to take the initiative to craft your relationships intentionally. Meet all of the senior leadership team and all of their direct reports. Make sure you map out all teams and functions. Understand the org structure in detail, including who owns what. Try to meet as many people as you can. Attending team meetings is a good method to quickly meet director and manager-level team members.
Don’t start relationships by asking detailed questions about roles and responsibilities. Make sure you take time to get to know people on an individual level (e.g., their family, what they do for fun, what motivated them to work at your company). This is a standard best practice, but it’s not always obvious to junior Chiefs of Staff.


2. Create a visible early win

There are many first-order ways to secure early wins in a Chief of Staff role. One way to do this early on is to lean heavily on your strengths, especially if you have strengths that are out-of-preference for the organization (e.g., detail orientation in a team accustomed to lax deadlines and imprecise metrics). The other way to immediately add value is to take on administrative tasks for your CEO. You need to prove to your CEO that you are 100% reliable and execute flawlessly. You should be a low-friction, low-worry team member for your CEO. If your CEO needs to review your work (e.g., check a report for errors, or check to make sure you booked a room for a meeting), you’ve failed.


The early win needs to be visible. If you are primarily working with the CEO, you need to find ways to ensure that others see the value you create. Don’t expect people to know the great work you’re doing unless you tell them in some way.


3. Automate your job

Traditionally, your work will shift from more process design and clean-up activity in your first 6 months to a larger and broader project portfolio thereafter. The key to being able to develop a high-impact portfolio is to minimize the process management and administrative aspects of your role.


My recommendation is to rigorously track your time for two weeks. Look for opportunities to streamline and automate the parts of your job that add value but are less useful to your development. For example, if you find that you spend a lot of time formatting board slides, you might decide to create standard templates for your team. Invest in developing these tools and processes to automate your routine responsibilities so you have time to take on more challenging work.


Sources of Career Value

The Chief of Staff role can be an incredible experience for individuals and a tremendous benefit for companies and CEOs. In addition to the opportunities I articulated earlier in this series, the Chief of Staff role confers several other sources of professional value.


1. Develop an executive mindset

Repeated exposure to senior executives is the best way to develop an executive-level mindset. Fortunately, the Chief of Staff role, by design, has built-in visibility to senior leaders, and this visibility is greater than you might otherwise get at this stage in your career.


Most people develop an executive mindset from climbing the corporate ladder. For example, if you want to move from director to VP, you need to learn what it means to be a VP by working with VPs. Exposure to a level of seniority is typically inversely proportional to your current level. For example, an entry-level employee typically has the least exposure to a CEO, and as a result knows the least about what it means to operate at a CEO level. While this fact is obvious, what most people don’t realize is that the difference is nonlinear due to how executives spend time. While a VP is one step from the C-level team, and a senior director is two steps from the C-level team, the amount of exposure the senior director has to the C-level team is disproportionately less than what might be implied by role distance. In many organizations, with increasing levels of seniority comes declining exposure to the next level of seniority. This is in part due to the increasing lateral responsibilities at higher levels of seniority (i.e., VPs generally spend more time coordinating with other VPs than senior directors spend working with other senior directors). This difference in exposure is one reason why it is increasingly challenging to progress as you achieve higher levels of seniority.


With these dynamics in mind, it becomes obvious why the Chief of Staff role is so valuable from an exposure perspective: you are thrust into the most senior dialogues in the organization before you’ve worked your way up the ladder yourself. Beyond C-suite exposure, you have significantly more interactions with senior leaders than you would in any other role. I think of this as an “unfair” level of exposure.


As a result of this unfair exposure, you will have a significant leg up in developing an executive mindset. You will quickly learn how senior executives operate and think — How does an operations leader make difficult tradeoffs? How does a CEO pitch potential clients? How does the CFO approach fundraising? What does it mean to uphold a company’s culture? You will get very good at thinking about accountability systems and organizational structures. You’ll interview senior executives. You’ll see executives challenge each other to improve performance and debate critical business issues. While developing an executive mindset is one of the most challenging barriers to growth, the Chief of Staff role is the ultimate shortcut.


2. Learn how businesses work

In addition to developing an executive mindset, the Chief of Staff role helps you learn how businesses really work. Operating across all departments means you will need to understand the basics of every function.


At first, this appears to be an easy task. A marketing department, for example, is responsible for figuring out how to promote and sell products or services. However, this intellectual understanding of business functions is wildly insufficient. To understand a department is to understand its constituent areas (e.g., for marketing: brand/creative, analytics, acquisition, product marketing, content marketing, digital, experience, PR, sales, etc.), its jargon (e.g., CPA, LTV, CAC, SEO, SEM, CPM, drip, lead nurturing), its analytic frameworks (e.g., LTV/CAC ratios, conjoint analysis, funnels, segmentation approaches), and its existential challenges (e.g., channel attribution, maintaining CPAs at scale, affiliate compensation).


The Chief of Staff role provides the broad exposure needed to truly understand how businesses operate in practice. Unencumbered by loyalties to any particular domain, you will be free to learn and understand the business better than almost anyone else. Continued exposure and participation in these senior conversations will eventually boost your practical knowledge to the top quartile in each discipline.


3. Figure out what you like

As I mentioned earlier, your portfolio presents a rare opportunity to deliberately test and explore different career hypotheses.


If you have constructed the right portfolio in a growing organization, you should be learning rapidly and taking on higher levels of responsibility every quarter. I recommend taking a break every quarter to reflect on the career hypotheses you are testing and ensure you are getting the experiences you need to advance your professional development. It is easy to get distracted by the broad set of content that you could learn at the expense of making improvements in the core skills and abilities necessary to progress in your career. The flip side to this challenge is that if you manage your portfolio carefully, you’ll have the freedom in the Chief of Staff role to figure out what you find attractive and fulfilling.


Chief of Staff Career Profiles

Below are profiles detailing the role design and career trajectories of three Chiefs of Staff. The first one is mine.


Healthcare Startup Major Retailer Professional Services Startup
Process 20%

• Managed and facilitated senior team meetings, strategic planning, and board meetings

• Implemented OKRs and KPIs

• Developed or supported other corporate processes (e.g., budgeting, cross-functional design)


• Managed and facilitated weekly financial reviews, facilitated quarterly business reviews, and ran customer insights process


• Managed and facilitated weekly executive team agendas, as well as internal committees

• Ran most internal communication processes

• Supported planning processes (executive & staff levels)

People 10%

• Supported org structure development


• Supported CEO’s most pressing daily issues


• Supported HR initiatives

• Supported CEO-specific initiatives (wrote speeches, researched potential board members, supported CEO’s membership in external organizations)

Portfolio 70%

• Co-owned (with CEO) the company’s understanding of the strategic and competitive landscape

• Supported strategic projects, including the development of an employer sales strategy

• Owned value-based care initiatives


• Supported capital request to investors

• Developed administrative assistant program


• Redesigned retail structure (P&L accountability, staffing models, ownership structures)

• Led financial projects (development of financial goals for different teams/units, long-term profitability expectations)

• Oversaw implementation of a new ERP

Post-CoS Role

Started a successful business unit based on portfolio experience and subsequently moved into a senior strategy role at the same company.

Pursued MBA and subsequently moved into a senior product and strategy role in the same industry.

Moved into a senior product and strategy role at the same company.


Advice for Transitioning out of the Chief of Staff Role

Stellar performance in a Chief of Staff role over 2-3 years can act as a career accelerant, particularly if you move into a new role within your organization. You will have proven yourself as a key contributor who has the trust of senior leaders, knows everyone, and can operate at a senior level. In a rapidly growing company, most of the roles you need today did not exist a year ago, and many Chiefs of Staff shape new roles within their company.


At the same time, transitioning to a non-Chief of Staff role within the same organization can be challenging. As Chief of Staff, you are probably accustomed to attending board meetings, running senior leadership team meetings, and having access and exposure to a wide range of information. You will likely give up some or all of these benefits. You might not know all the confidential issues discussed behind closed doors, which issues are top of mind for each executive, or how internal politics are evolving. You will have to quickly get comfortable operating without the full context of the organization. In general, this transition is easier than it might appear, but it does constitute a significant mental shift.


The other mental shift that ex-Chiefs of Staff find challenging is fully adapting to their new scope and responsibility. The narrowing of scope can be a challenge as it can take some time to realize that you are now not empowered to solve any problem that you observe. You should act like an owner of the organization, but realize that once you leave the Chief of Staff role, it’s not your responsibility to handle many of those issues outside of your core domain.


It is also important to carefully reassign explicit and implicit responsibilities to others as part of a transition plan. This is typically easy for explicit duties, but implicit duties can fall through the cracks. For example, one Chief of Staff friend didn’t fully appreciate the extent to which she was bridging internal communication gaps among teams with cross-functional dependencies. Once she left the role, it took her colleagues several months to figure out how to work together without the Chief of Staff’s guidance.



The Chief of Staff role, though challenging, can be an immensely rewarding and transformative experience. I hope this guide helps you in your own journey, and don’t hesitate to reach out with any comments or questions.