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.