The Chief of Staff

"You are not made a leader. You decide to become one." - Chris Fussell


I hired a Chief of Staff in January for the first time in my career.

Previously, I believed that having a Chief of Staff/Executive Assistant was a sign of weakness (i.e. you couldn’t keep up without someone helping you) and/or hubris (i.e “Look at me, I have an assistant!”). I also thought it was a poor use of capital (financial and human). I was wrong. 

I realized that my previous beliefs were incorrect for 3 reasons:

  1. A great Chief of Staff can positively impact the organization, perhaps more so than they impact the leader they are directly supporting.
  2. It’s a tremendous opportunity to develop talent in an organization, by giving them a broader view.
  3. It’s an investment, not an expense. 

Succinctly said, a Chief of Staff role is more about helping the organization than a single leader. That’s a huge responsibility. That being said, there is no real standard for how these roles are utilized. I have seen some organizations treat them as secretarial roles (get coffee, etc), others as more transactional (briefing documents and scheduling), and others as a strategic adviser. 

But, if the 3 justifications above are correct, I believe we should give more thought to defining a standard for the role.


In the book, One Mission: How Leaders Build a Team of Teams, Chris Fussell writes about his role supporting General Stanley McChrystal. When McChrystal first asked him if he wanted the role, Fussell responded:

“Sir, I don’t think anyone in our community dreams of being an aide, and it's certainly never a position that I’ve sought. That said, I’ve felt something change in our organization over the past few years - we’re running differently, and better. An opportunity to see behind the curtain and understand how this is working...well, that’s fascinating to me.”

This response highlights not only his curiosity, but his desire to have an impact in a role that may otherwise be marginalized as an ‘aide’. Aptitude is important, but attitude is even more important. And, this is the right attitude to bring to the role.

Fussell goes on to share a framework for a Chief of Staff. It is four quadrants, with each one representing a different phase of development of the individual and their impact on the organization. He suggests that the Chief of Staff starts in quadrant 1 and develop clockwise. Some will reach quadrant 4, others will not. The quadrant that one reaches does not necessarily indicate their effectiveness. The framework presciently distinguishes between responsibilities that impact the Leader vs. the Organization. See here:


While the specifics in each quadrant will vary by organization, leader, and the individual that is Chief of Staff, I believe its a great starting point for a standard.


My experiment worked out very well. The individual ‘graduated’ in October, taking a key operational role in the organization. There are 3 things that stick out about this person:

  1. His written communication skills were exceptional. Clear, concise, fact-based, and thoughtful.
  2. He earned the respect of the organization through impact, not ‘networking’.
  3. He made our team better. 

I am now convinced that the Chief of Staff role is valuable. The standard for every organization will be different, but this framework is a good place to start.

Owner vs. Employee

“Have no fear of change as such and, on the other hand, no liking for it merely for its own sake.”- Robert Moses


Robert Moses shaped New York as we know it today. He built nearly every road: the East River Drive, Major Deegan, Van Wyck, West Side Highway, Cross-Bronx Expressway, Long Island Expressway and any other you can imagine. He built 416 miles of parkways. He built every bridge: the Triborough, Verrazano, Throgs Neck, Henry Hudson, Whitestone, etc. He built Lincoln Center and the United Nations. He built 600 playgrounds in New York City. He was America’s greatest builder and he personally shaped a city that many regard as the greatest in the world. But, how?

The cost of progress was significant. Not just in the form of dollars, but the trade-offs. Moses’ plan displaced an estimated 500,000 people from their homes; this complicates his legacy. His decisions were unpopular with many, yet he persisted with his priorities. Over a period of 44 years, a combination of power, personality, and influence enabled him to accomplish something that no one else could imagine. He had an ‘owners’ mindset; he was building for the long term, thinking systemically, not tactically. Any employee of the local/state government at the time, with their myopic goal of getting elected/re-elected, could not accomplish the same priorities. They had a ‘renters’ mindset: short-term and transactional.

Owners can do things that employees cannot. Not because of their position, but because of their mindset.

Read the rest on Medium.

Disproportionate Outcomes

“Give me a place to stand, and I shall move the Earth with it” — Archimedes



I spent some time with a good friend a while back. We started taliking about some philanthropy work that he and his wife are doing for children with special needs. This resonated with me, as my wife spent a number of years of her life working at a school for children with special needs. I mentioned to my friend that we were always amazed at the progress that the children could make with the right tools and assistance. At the time, we made it a habit of giving money to the school to purchase more tools (computer equipment and other learning aids). This definitely had an impact on that school and those children. 

My friend went on to say that he was giving to an educational institution, who was training students to teach children with special needs. He added, “I always try to give where there is the most leverage”. While ‘leverage’ is perhaps an overused word, his comment was the perfect example of the true application of leverage. If you train young adults to teach children with special needs, then you can probably touch hundreds or thousands of children over a reasonable period of time. By contrast, if you give tools to one school (like I have done in the past), you only impact a much smaller population of children (i.e. those that go to that school). 

Now, giving is giving and helping is helping…and there is probably no wrong way to do it. But, for me, this was a powerful lesson in leverage. 

Read the rest on Medium