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.