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.

The Chief of Staff Guide — Part 3: Common Pitfalls

August 25th, 2018

This is the third article in a four-part series. In the previous article, I discussed the Chief of Staff's three essential responsibilities — Process, People, and Portfolio — and provided guidance on how to shape those responsibilities.


Key Traits

The performance characteristics of a Chief of Staff are higher than most comparable roles at its level. Chiefs of Staff must be comfortable operating with contradictory traits:

  1. Independent, requiring little direction, but also highly collaborative
  2. A broad thinker who can handle the details
  3. Assertive and confident while being open-minded and humble
  4. Proactive but comfortable reacting to fires
  5. Comfortable with senior executives and board members, while also approachable and fluent with entry-level staff


In addition to the contradictory traits, a Chief of Staff must also display several non-negotiable clear traits:

  1. Trustworthy (e.g., you treat confidential matters and private opinions as such)
  2. 100% reliable
  3. Willing to "touch the nerve" to get to the root of tough issues
  4. Analytical horsepower
  5. Ownership mindset


These performance requirements are intense, and the Chief of Staff role is particularly challenging as a result. Beyond these attributes, the Chief of Staff will have to navigate a handful of tricky potential pitfalls.


Common Pitfalls

1. Failing to build and maintain trust with conflicting clients

The Chief of Staff has conflicting clients. You are responsible to your manager. At the same time, like all leaders, you will learn things that you need to keep in confidence. The structure of the role lends itself to suspicion, and the Chief of Staff cannot be a spy. You have the ear of the CEO and can therefore have a disproportionate effect on someone's career. It is easy to lose trust, and a loss of trust is a problem that spreads quickly and is almost never recoverable. Each Chief of Staff and CEO will have to navigate these trust questions early on.


2. Failing to clarify your authority

Contemporary corporate culture eschews authority as a primary means to achieve goals. However, authority is still present in any hierarchical organization, and the Chief of Staff's ambiguous authority can pose material challenges.


What kind of authority does the Chief of Staff have? If someone's manager is on a plane, and you ask them to do something that is both time-sensitive and disruptive to their other priorities, will they do it? Should they do it? Whose voice do you use: yours or the CEO's? Are you the principal or the agent?


Seniority and authority are often ambiguous, and perceptions may vary widely. My recommendation is to proactively establish the Chief of Staff as an independent role vs. an "assistant to" role. Your requests or opinions are yours unless you label them as the CEO's. You should avoid over-reliance on the CEO as a source of authority. People should work with you because of who you are and not because of some implicit threat that you will escalate to the CEO. However, the latter tool is useful if used rarely and strategically.


Since your title is ambiguous, you should also figure out how to introduce yourself internally and externally — e.g., "I'm the Chief of Staff, which means I work with [person/team] to do [thing]. Right now I'm focused on [portfolio project]." This might appear to be a minor point, but it's critical to proactively shape perceptions, and how you talk about what you do matters.


3. Underestimating organizational savvy

While organizational savvy is a common developmental focus for emerging leaders, it is particularly acute for Chiefs of Staff. In an individual contributor role, the primary measure of success is the content and outcomes of your work, which are usually in your control. In the Chief of Staff role, part of your ability to create impact comes from influencing others. Do not underestimate the importance of individual relationships, and consider developing your own toolkit to motivate, persuade, nudge, and align individuals and teams.


4. Lack of courage

Courage is critical to performance in the Chief of Staff role. You will need to lay out expectations, give feedback, and have difficult conversations. Do you have the courage to talk to a senior executive when expectations are violated? Do you have the courage to tell a senior executive that his strategy doesn't make sense? Or that a direct report he thinks is great is widely viewed as underperforming?


You will also need to be comfortable providing senior executives with feedback in order to operate proficiently as a Chief of Staff. While most Chiefs of Staff struggle to give senior executives feedback, recognize that hearing feedback from you is less threatening than receiving feedback from C-suite colleagues. As long as you lead with EQ and make it clear that your goals are aligned, executives will generally appreciate it. I highly recommend Crucial Conversations and Crucial Accountability for further guidance on this topic.


5. Fearing the content

Taking on an initiative in a new domain with unfamiliar content can be daunting. Chiefs of Staff fail when they become afraid of the content. The best Chiefs of Staff lean in, do their homework, and tap into both internal and external experts to ramp up quickly.


Any smart person can learn the content. Remember that in most organizations, as soon as people get good at their job, they are often promoted into new roles in which they are not fully competent. We're all figuring it out to some degree, so there's no reason the Chief of Staff role would be any different.


6. Failing to effectively switch contexts

The diversity of content combined with the broad scope and responsibility can be overwhelming. In a single day, a Chief of Staff might handle topics that traverse a half-dozen departments, external partners, and sensitive internal issues — as large and abstract as long-term planning, to as small and as detailed as the seating arrangement at a board dinner. It is both difficult and completely necessary to figure out how to organize your portfolio, personal systems, and time to enable deep work on big projects while maintaining a diverse array of processes and attending to people matters. Individuals who cannot manage their time or who struggle with frequent context switching should not attempt Chief of Staff roles.


7. Failing to transition from consultant to leader

The Chief of Staff portfolio often starts out with consultative work. Transitioning to leading and owning a project or domain can be a difficult mindset shift, particularly for individuals with limited operating experience. Failure to make the transition often shows up as traditional leadership gaps — e.g., asking for too much detail, a lack of a strategic vision, a reliance on others for critical thinking, or getting stuck in too much analysis. However, these gaps can be easy to miss at first. Chiefs of Staff need to recognize what role they are playing across their portfolio and ensure they aren't consulting when they need to be leading.


8. Failing to set themselves up to get constructive feedback

As Chief of Staff, you will make mistakes in front of the most senior people in your organization, which presents a fantastic opportunity for feedback. However, since you might work with many individuals in a limited capacity, it can sometimes be difficult to get enough data points to elicit meaningful feedback from multiple executives. In addition, if the Chief of Staff role is scoped poorly, the functions of the role will limit feedback. For example, it will be hard to get meaningful feedback on your strategic thinking skills if you spend 50% of your time setting up meetings. Partnering with executives on your portfolio project can help set yourself up to receive valuable developmental feedback.



Despite its potential pitfalls, the Chief of Staff role can be incredibly rewarding. I explain how to make the role work for your career in the final article in this series.

The Chief of Staff Guide — Part 2: Shaping the Role

July 22nd, 2018

This is the second article in a four-part series. In the first article, I provided an introduction to the Chief of Staff role and discussed how it varies by company stage and role independence.


Creating Value

The structure of the Chief of Staff role affords two unique ways to create value:


1. Informational

As Chief of Staff, your knowledge of what's happening in your organization is probably second only to the CEO. Not only do you have broad content knowledge across departments, but you also understand how the CEO and executive team think and know what's top of mind. As a result, the Chief of Staff can connect dots across projects, people, and departments to improve decision-making and make the organization work better. Beyond sharing facts, the Chief of Staff can add value by integrating explicit knowledge of the business with exposure to topical business issues in order to provide relevant insights or feedback. For example, a Chief of Staff might combine knowledge of the current state of the technology roadmap with prior exposure to previous technology trade-off conversations to help a team frame and prioritize their upcoming technology requests. The Chief of Staff's informational reservoir enables these multifactorial insights.

2. Positional

The Chief of Staff has the implicit — and often explicit — blessing of the CEO and senior leadership team, which gives you air cover to dive into issues across the organization. As I cover in the Pitfalls section, this closeness to the CEO is a double-edged sword that Chiefs of Staff must carefully navigate. While I highly discourage the use of positional authority, the Chief of Staff can help eliminate roadblocks, motivate behavior, and overcome resistance by signaling that a particular topic is important to the organization. This positional benefit also works to your advantage externally: if the CEO trusts you, then outsiders should trust you too, which gives you an excuse to get involved in senior-level dialogue with external leaders.

The combination of informational advantages with positional benefits enables the Chief of Staff to act as an extreme owner who is empowered to solve problems and make unique contributions across the organization. The core responsibilities of a Chief of Staff reflect these sources of value.



Core Responsibilities

While every role is different, the core duties of a Chief of Staff generally fit into three categories, each of which allows the Chief of Staff to uniquely increase the effectiveness of the organization.

  1. Process: Assess, redesign, and manage key corporate processes.
  2. People: Take the pulse of internal teams and address or advise on issues.
  3. Portfolio: Own a portfolio of projects that drive the business forward.



1. Process

Organizational processes break as a company grows. A bad process is generally better than no process, but a good process can provide an executive team with significant leverage. Process is especially helpful for staff teams because it reduces daily friction (e.g., Who must approve compensation bands for a new job type? When are we deciding who needs to present at the board meeting? How do we determine whether my new initiative gets funding?). In growing organizations, the Chief of Staff might redesign processes every 6-12 months as teams and needs evolve. At the same time, building and running processes provides the Chief of Staff with an unprecedented window into how companies operate.


Chiefs of Staff are often responsible for the following corporate processes:

  1. Senior leadership meetings
  2. Staff meetings
  3. Board meetings
  4. Planning processes
  5. Performance management processes
  6. Cross-functional processes
  7. Internal communications


Senior leadership meetings

Companies typically have a weekly meeting of C-level executives to discuss, debate, and decide major topics ranging from broad strategic matters to specific confidential issues.


While the administrative task of managing the agenda often provides leverage for the CEO, the larger opportunity is for the Chief of Staff to help set the agenda. This is one of the dominant sources of influence for a Chief of Staff and is one of the greatest benefits for the company. By managing the agenda of the organization's most senior leadership team, the Chief of Staff decides what gets discussed. You can nudge the organization toward issues that need additional attention based on your broad view of the business. For example, you can use a C-level presentation as a forcing function to get a team to clarify their strategy or galvanize an important decision. The Chief of Staff can also help individuals tee up the right type of dialogue in these C-level conversations. On the other hand, for objectives that are on plan, a presentation at the senior leadership meeting can give that team a well-deserved boost.


In addition, rapidly growing teams sometimes forget to bring important topics to the executive team for discussion. This can become a chronic problem, especially for topics that appear elective but require explicit discussion (e.g., compensation and benefits philosophy, company culture, and employee feedback). The Chief of Staff should work with leaders to bring these topics to the forefront on a regular basis.


Staff meetings

The staff meeting is typically a biweekly or monthly meeting for VPs and sometimes director-level leaders as well. The goals of this meeting are to keep the broader leadership team informed of organizational priorities, review progress against priorities, and solicit input on key issues. The Chief of Staff often manages the agenda, runs the meeting, and will occasionally handle important follow-up items. The Chief of Staff can steer the organization toward specific topics by setting the agenda and managing discussion the time on each topic.


Board meetings

The CEO owns the board meeting, and the Chief of Staff typically serves in two capacities.


First, the Chief of Staff can own the process of producing board materials. This administrative function requires laying out detailed timelines and check-ins with all contributors, integrating the materials, and producing a final deck that is consistent across all departments in both format and content. The Chief of Staff should meet with executives early to co-create a high-level presentation draft, work through deck iterations, host live practice sessions to provide feedback, and ultimately edit and own the final materials.


The more strategic source of value is in enabling the company to tell a coherent narrative that focuses the board's attention on the key business issues. Recognize that experienced executives are such experts in their space that many need help crafting narratives to external audiences who aren't steeped in their content. Since you understand a department's content but also see the larger picture, you are uniquely positioned to serve as a thought partner to contributing executives. A Chief of Staff should up-level the content to make it appropriate for the board by removing irrelevant information in some places and asking for more detail in others. The Chief of Staff might also remember prior board feedback on a given topic and use that insight to help executives preempt board questions. The Chief of Staff provides the critical eye that executives need to refine their individual narratives (e.g., "Your comment states that retention improved year over year, but the graph tells a different story, and another team is taking credit for the same improvement.") as well as the overall narrative (e.g., "Why is 75% of your presentation about customer retention when it wasn't on the top 10 priorities list we shared with the board at the beginning of the year?").


The Chief of Staff usually attends the main session of the board meeting. In some organizations, the Chief of Staff will attend a committee meeting but almost never attends the approvals session. Board meeting minutes are the responsibility of the company secretary, and for legal reasons the Chief of Staff should not take notes during board meetings.


Working with the board is an incredible opportunity for a novice Chief of Staff to learn what matters in an organization, how to communicate the company's activities and perspectives, and how smart outsiders with inside information think about your business.


Planning processes

Organizations typically need a variety of planning processes, including annual strategic planning, annual financial budgeting and planning, and quarterly priority setting and alignment. A company might also have processes for technology planning, real estate, and recruiting, among others. The Chief of Staff should fully understand all of these processes, and in some cases own or support these processes in partnership with department leaders.


Performance management processes

Performance management processes reflect the idiosyncrasies of a company's leadership structure and business model. Broadly, the Chief of Staff should ensure the right systems are in place to measure progress and address variance. You should think about the company's goals, determine who is responsible for each objective, evaluate the processes to achieve those outcomes, and look for deviations from expectation. For example, the Chief of Staff might own the top-level KPI/metric reporting dashboards in partnership with the CFO and department leaders. I have also seen Chiefs of Staff manage processes related to monthly financial and operational performance, recruiting, sales, and real estate. While managing the performance of the core operational drivers of the business is generally best owned by the CEO, CFO, or COO, the Chief of Staff can set up the macro processes, instrument metrics, and create reporting and accountability mechanisms.


Cross-functional processes

Ongoing cross-functional processes can be challenging, particularly when multiple departments attempt to co-own a process and struggle to arbitrate differences. A neutral Chief of Staff can help design and run cross-functional processes, provided these processes do not require significant domain expertise. Cross-functional compliance or security meetings, for example, are generally best left to their respective domain leaders. Chiefs of Staff have successfully managed cross-functional processes to design new services (i.e., nexus of operations, finance, technology, and marketing), launch new products (i.e., nexus of marketing/PR, internal communications, technology, and operations), and manage complex deals (i.e., nexus of sales, operations, and finance).


Internal communications

A Chief of Staff can, at a minimum, proactively develop an approach to internal communications, which is a common gap in growing organizations. Since you will have your ear to the ground, you can also advise the CEO and executive team on specific communication gaps. In some organizations, I've seen Chiefs of Staff go so far as to create and operate an internal communications function.


It's worth noting that better process often helps create better decisions. By laying out who needs to make different types of decisions and with what information, the Chief of Staff can improve organizational decision-making. In some cases, the Chief of Staff might even take decisions off executives' plates and empower their teams to decide on their own. In other cases, important decisions are made by the wrong people, and the Chief of Staff can change the decision architecture to reflect the correct set of constituents. Driving clarity on ownership, decision authority, and the process to get from question to answer can be a force multiplier for a growing company. In addition, your exposure to the decision-making style of the executive team will help you advise department leaders on how to frame decisions that are ultimately owned by the senior team.



For general advice on corporate process and management systems, I recommend Growing Pains and High Output Management.



2. People

The Chief of Staff is uniquely positioned to improve the organization by improving the functioning of its people.


First, the Chief of Staff should constantly take the pulse of the organization. Some CEOs ask Chiefs of Staff to formally meet with the leaders of key functions on a regular basis to discuss headwinds, tailwinds, and hot topics. Formal or informal, knowing how people are doing at all levels of the organization is important to success in the role. Create systems that allow you to check in with teams you don't see too often. This might involve travel to a different region or corporate division, or simply a quarterly lunch schedule with various team members with whom you don't frequently interact. Ask yourself: Who is doing well and who is struggling? Where are people stuck? Where are people out of the loop? By keeping your ear to the ground, you will become aware of issues and often resolve them without involving the senior team. You will serve as a connector and fill in gaps in information, and you will get people the resources they need to achieve their goals.


Depending on the maturity of the leadership team, the Chief of Staff can also help resolve disputes. In general, the Chief of Staff should try to flag disputes to the relevant parties and encourage them to resolve it, and only get more involved if they are unable to handle it themselves. The mere act of highlighting a dispute is often sufficient to prompt a resolution. This is particularly true for situations where paralinguistics and interpersonal style are the primary cause of internal friction. The Chief of Staff generally knows most employees and can be helpful on these matters. Regardless, the Chief of Staff should generally function primarily as an advisor and advocate than as an arbiter or peacemaker. If the Chief of Staff is spending a significant amount of time resolving disputes, there are likely deeper problems with the people, process, or both.


Finally, the Chief of Staff generally has the positional ability to join meetings and observe how things are going first-hand. You might do this for learning purposes or because you suspect there are issues that would benefit from your neutral assessment. As a trusted advisor to the CEO and senior team, the Chief of Staff can be instrumental in informing the executive team's perspectives related to people. The Chief of Staff can talk to people with an external lens, dissect different viewpoints, and synthesize perspectives across domains. Herein also lies one of the largest pitfalls of the Chief of Staff role — trust — which I will address in the Pitfalls section.



3. Portfolio

Typically, the largest part of the Chief of Staff role is a portfolio of initiatives.


The CEO will generally populate the Chief of Staff's portfolio in the first 6-9 months. In rapidly scaling organizations, the Chief of Staff typically begins by developing the foundational organizational processes discussed above. However, most Chiefs of Staff begin to have the freedom to shape their portfolio in short order.


Since you have a wide lens on the organization, you will see dozens of potential projects or domains to add to your portfolio. While selecting priorities is important in any role, deliberately crafting the right portfolio is critical to success as a Chief of Staff. The opportunities are endless, and the Chief of Staff's vantage point will afford more options than any other role.


I will share a personal example to illustrate this challenge. About six months into my tenure I drafted a list of ten potential portfolio initiatives:

  • Three were early ideas that appeared fun but were strategically unimportant, so I avoided them. When later pursued by others, these ideas all ended up as dead-ends.
  • Two were big projects that I thought needed dedicated owners instead of Chief of Staff support. We eventually hired leaders in these areas and they were successful.
  • Three were clean-up projects that I could have taken on but didn't. They would have provided me with good learning but had limited upside for the organization. They continued to flounder for a while and were eventually absorbed into other roles.
  • Two looked like game-changing opportunities for the organization but were in domains I knew nothing about (more on this pitfall later). I ended up taking one on of them, which I eventually evolved into my initial post-Chief of Staff role. It had a significant positive impact on the trajectory of the organization and my career.


As you can tell, I could have easily selected fun projects that would have likely led to dead-ends, attempted to take on meaty domains that ultimately needed dedicated owners, or tackled clean-up projects that wouldn't have driven top organizational priorities. Selecting the right portfolio is critical.


Your portfolio should optimize for three factors:

  1. Impact for the company, often by solving gaps or turbocharging important initiatives
  2. Impactability (i.e., the degree to which you can make progress)
  3. Benefit to your professional development and career path


Here's how I would go about evaluating each factor:

1. Company Impact
Set aside your current skills and abilities and determine what business outcomes would have the most impact for your company. Some Chiefs of Staff meticulously analyze each business driver and contemplate future possibilities. A faster method is to look for gaps, which typically come in two categories: gaps in current priorities and gaps in future priorities.


Current priorities

Look for corporate priorities that lack sufficient investment or attention. These areas might currently be unmanaged or undermanaged, or they might lack a natural owner altogether. If you look at an organizational priority and struggle to see how the team will achieve it, you may have uncovered a valuable gap worth filling. In addition, you should consider areas that are well-covered but might benefit from extra time or attention — opportunities to turbocharge key company priorities. In addition, ask your senior team for suggestions on gaps to fill or initiatives to accelerate.


Future priorities

Juxtapose the broader vision and long-term goals of the company with current priorities and short-term activities. What is really important but nobody is talking about? What is going to be on the corporate priorities list in 2-3 years? These areas might arise from thinking strategically about industry movements and the competitive landscape, or simply by thinking about what the company needs to do to achieve its goals in the medium to long-term. Consider the top strategic questions within each domain or department and how they will evolve in the next few quarters. Following your curiosity should lead you to gaps between current investments and the future state. These gaps are often prime projects to consider in your portfolio evaluation.



2. Impactability
After identifying high impact initiatives, the next step is to carefully determine where you can have impact. These considerations will be specific to your own skills and abilities, current organizational resources, and the risk of each initiative.


Be wary of projects that sound like "This person isn't doing his job, can you help him do it?" These initiatives will likely score low on impactability and are typically a recipe for failure. In addition, carefully consider the pros and cons of any initiative that requires you to build a major function or new department. There is a big difference between developing an HR process and running an HR team. Some core functions require technical expertise that a Chief of Staff is generally not well-positioned to band-aid. Factor in these considerations to evaluate impactability.


3. Professional development and career path
Your portfolio will serve as your primary opportunity to proactively drive your professional development. Consider development opportunities in terms of content areas (e.g., knowledge of marketing or familiarity with HR issues) and skill/ability areas (e.g., soft skills, such as managing ambiguity or negotiation tactics, or hard skills, such as financial modeling or data analysis). Ask your senior team colleagues for recommendations on what might be most beneficial for you.


You should also have hypotheses about your career path that you can test through your portfolio. Would you rather strategize about businesses or be accountable for operating outcomes? Do you prefer to operate at the 30,000-foot level or be on the ground wrangling day-to-day issues? Do you like investor-facing work? Sales? Managing conflict? Don't ask your CEO to guess. Try to shape your portfolio so that you can deliberately test your career hypotheses while simultaneously adding value to your organization.


Finally, make sure your portfolio has a cap, as it is easy to take on too much work. Great work comes from having time to go deep and focus on a specific problem, so try to stay focused but flexible and responsive to the organization's highest needs.



Now that I have articulated how the Chief of Staff role works, I turn my attention in the next article to the common pitfalls endemic to the position.

The Chief of Staff Guide — Part 1: Intro

May 12th, 2018

This is the first article in a four-part series about the Chief of Staff role. In subsequent articles, I explore how to shape the role, how to avoid common pitfalls, and how it advances your professional development.


Over the past 5 years, I've received many calls for advice about Chief of Staff roles.


I've formulated reflections on how to make the most of the role through conversations with individuals contemplating the role for the first time, CEOs considering hiring a Chief of Staff, and current Chiefs of Staff looking for guidance. This guide is intended to help any of these constituents, though for linguistic simplicity I've written this to current and prospective Chiefs of Staff.


Serving as Chief of Staff can be a career-changing experience. But it's not for everyone. It's a difficult role, and no two Chiefs of Staff have the same journey. It's highly dependent on the fit between the Chief of Staff, the company, and the CEO. You will gain broad company exposure and C-level visibility far above your pay grade, but risk operating as a glorified assistant if the role is poorly designed. You will have internal air cover to help the organization achieve its most ambitious goals, but the work of developing and maintaining the trust to do that borders on Sisyphean. It's a high beta role — higher risk, higher reward. The role is what you make it, and this guide is designed to help you make it successful.


Drawing on my experience, as well as the experiences of other Chiefs of Staff, I will address three major topics:

  1. How to shape the role
  2. How to avoid common pitfalls
  3. How to manage your career path


What is a Chief of Staff?

The Chief of Staff title is attached to a range of roles spanning from primarily administrative to highly strategic. Some Chiefs of Staff are executive assistants with aide-de-camp responsibilities, while others operate as senior executives with broad oversight. The liberal use of this level-less title causes confusion for those considering the role.


I will focus on Chief of Staff roles that are primarily strategic — not roles that use the title to reflect "assistant-to" responsibilities (e.g., an executive assistant who attends meetings and ensures follow-ups are completed). As with any role, the Chief of Staff needs to enable his or her boss — typically the CEO — to be successful. However, the Chief of Staff has additional conflicting customers, including the executive team and the company as a whole. As I will explore, the Chief of Staff will need to dynamically interpret this broad mandate in the context of his or her own organization.


While I will confine my discussion of the Chief of Staff role to those serving as a strategic (vs. administrative) partner to a CEO or other senior executive, the role still varies by two principal factors: the stage of the company and the independence of the role.



Chiefs of Staff are often hired into rapidly growing organizations. During periods of intense growth, the fundamental structure of an organization shifts, and almost everything that worked in the prior structure breaks. Organizational structures need to change, decision-making authority becomes unclear, scope and turf issues arise, new people are needed at multiple levels, and basic processes across the organization — from financial planning to code releases — need to be created and destroyed. As these fundamental structures evolve, a Chief of Staff can help manage growing pains by designing and running a new "operating system" for the organization. Chiefs of Staff also exist in more established and slower-growth organizations, but I don't know enough to represent that end of the spectrum.



The second factor that defines the role is the level of independence the Chief of Staff enjoys. At one extreme is the bodyman model, where the Chief of Staff travels with the CEO, attends most of the CEO's meetings, prepares briefs, takes notes, and acts on follow-up items. This conjoined model lends itself to a more administrative focus. At the other end of the spectrum is the solo model in which the CEO and Chief of Staff primarily function independently. They might spend a few hours together each week, but they won't travel or attend many meetings together, and the Chief of Staff primarily sets his or her own agenda. There are many gradations between these two extremes.

This series will primarily focus on the strategically oriented, primarily independent Chief of Staff role at high-growth companies, which was my experience and the experience of many of my ex-Chief of Staff colleagues. In this capacity, you might expect to serve in the Chief of Staff role for 2-3 years before moving on to other responsibilities — more on this in the Career Path article.


In the next article, I describe how the Chief of Staff creates value and the primary duties that reflect this value. I also provide guidance on how to shape the role to maximize impact across the Chief of Staff's broad range of duties.

Forget the Medical Chatbots. Let’s use AI to Fix Healthcare Administration.

December 21st, 2017

I am puzzled by the interest in AI medical diagnosis chatbots. Dozen of startups are tackling one of the most difficult technical problems — clinical diagnosis — with fairly immature technology and no real business model. It's even more intriguing when you realize there are billion dollar opportunities in administrative process automation, which is a massive pain point for almost every medical practice in the country. It's also much simpler than algorithmic medical diagnosis.


using artificial intelligence (AI) for healthcare administration


Context: We're Spending Hundreds of Billions of Dollars on Automatable Clerical Work

Unless you've worked at a provider organization or insurer, you probably aren't familiar with the colossal administrative engine that makes our healthcare system tick.


Let's start with the basics. We spend about $3.4 trillion annually on healthcare in the United States. About one third, or $1 trillion, is spent at hospitals. About 25% of all hospital spending — over 1% of GDP — doesn't go to care delivery. Instead, these dollars — about $250 billion, or $750 per American per year — fund hospital administration (per a 2014 Health Affairs study).


Some of those expenses are necessary. Hospitals are complex organizations that require many non-clinical staff. However, a large portion of that expense is clerical work that adds no value for the patient.


Keep in mind that the $250 billion figure only covers hospital-based administrative expenses.


About 25% to 30% of healthcare spending is on ambulatory and outpatient care, which includes most healthcare services that occur outside the hospital, such as primary care, specialty care, outpatient surgeries, and diagnostic services. Benchmarks suggest that at least 20% of all ambulatory spending goes toward administrative support staff. In fact, the average primary care provider in a private practice is supported by almost five non-clinical staff (per Medical Group Management Association benchmarks). Ambulatory and outpatient administrative expenses add another ~$170B in costs each year.


If only 25% of this $420B in annual expense is automatable or augmentable clerical work, we arrive at a total opportunity of over $100B in annual costs. Though some of those costs are outsourced offshore, the domestic clerical burden is enormous. Nearly 60,000 Americans work as medical transcriptionists, over 200,000 are medical records technicians, and another 630,000 act as medical assistants (per the Bureau of Labor Statistics). I didn't even include the administration expenses incurred at insurance companies, pharmacies, home health, nursing homes, device suppliers, or in government — which makes up the other ~40% of healthcare spending.



Enter AI

While outpatient practices are rife with operational inefficiencies, I'm going to focus on three clerical (i.e., non-clinical) areas where AI — or its simpler cousin, Robotic Process Automation — can yield the most value.


1. Revenue Cycle & Credentialing

Revenue cycle management (RCM) is the core of getting paid in healthcare. It's a very complex topic with many opportunities for automation. RCM tools offload some of the complexity to rules engines but still leave a lot of manual processing to humans. In addition, credentialing a clinician with an insurance company — a process in which the insurer validates that the provider is eligible to render care as an in-network provider — is a tedious and time-consuming exercise that adds to a practice's administrative load.



  • Coding & Claim Generation: Practice staff have to create electronic claims after each visit based on the notes in the electronic medical record. They have to scrub each claim based on a series of rules to ensure it will get adjudicated correctly by the insurance company, and these rules can change at any time without advance notice.
  • Denials & Appeals: Resubmit rejected claims. Often involves calling insurance companies, reviewing coverage documentation, and consulting coding guidelines to select the appropriate codes for each insurance company.
  • Credentialing: Submitting detailed personal and educational histories for every billing provider to each insurance company every few years.



2. Insurance Administration

In addition to submitting claims for payment, practice staff spend a lot of time helping patients and clinicians navigate the insurance system.

  • Evaluating Insurance Coverage: A patient receives a referral from her PCP to a cardiologist. The practice staff call the insurance company to confirm the cardiologist is in-network and accepting new patients.
  • Managing Insurance Authorizations: A patient receives a referral from his PCP for an abdominal CT to rule out appendicitis. In order for the insurance company to cover it, a practice administrator needs to log into a portal and provide documentation. Alternatively, an insurance company might call the practice to conduct a "peer-to-peer" (P2P) with a clinician. During a P2P, a clinician needs to explain why a patient needs a particular service. A similar process is required for pharmacy denials for off-formulary prescriptions (e.g., "Yes, this patient needs the Tier 3 medication because she had an allergic reaction to the Tier 1 preferred option.").
  • Explaining Insurance Benefits: A patient does not understand his benefit design, and the practice staff needs to explain it to him, along with providing an out-of-pocket cost estimate for his high deductible health plan.



3. Document Management

A significant portion of clerical overhead is spent managing documents, including responding to medical records requests, triaging incoming documents, and completing medical and administrative forms.



  • Chart Extraction: A law firm requests medical records for a patient. Practice staff need to identify the patient and excise sensitive information from the medical records (e.g., mental health history). Then they need to mail or fax the records and generate an invoice.
  • Document Triage: During a 30 minute period, six specialist reports, two radiology reports, and twenty medication refill requests arrive via fax. Practice staff have to classify each document (CT scan or CT angiogram?), triage what's time sensitive, and route each document to the correct patient's chart, often by matching names and dates of birth. If a name or date of birth is inaccurate, they have to destroy the document, contact the sender, and request a new set of records to avoid a HIPAA violation. If the fax is illegible, they have to contact the sender to have the document re-sent.
  • Form Generation: A patient needs their PCP to complete a four-page FMLA form, a referral for FSA reimbursement, or a back to school form. Support staff take a pass at filling out the form, and pass it to the PCP to complete the clinical components.



In addition to lowering the cost of care, automating clerical aspects of physician practices would help reduce errors, speed up access to care, and shift our spending to higher-impact roles — reskilling medical billers as care navigators, home health aides, and health coaches. Moreover, there are countless clinically-focused AI opportunities, such as augmenting population health outreach, extracting relevant clinical data from medical records, and facilitating care coordination.


So, chatbots might be fun, but there's probably a real business to be built automating the clerical operating system of the medical economy.