Volume 3: Playing midfield, not middle management

a16z is launching a Chief of Staff bootcamp, and the Chief of Staff is going mainstream. The rise of the Chief of Staff title is diagnostic of how the world has shifted.

Organizations were built around predictable inputs, fixed expertise, and clear lanes, which make sense in a kind world. In wicked conditions, predictable inputs become persistent ambiguity, fixed expertise gives way to adaptive systems, and clear lanes evolve into dynamic control of time and space.

The internet was the first major catalyst pulling us out of post-war equilibrium. AI is a powerful accelerant, pushing the balance further in wicked’s favor.

Wicked conditions force organizations to reorganize around interaction rather than architecture. Organizations now demand fluid coordination, upping the ante on glue.

Chief of Staff is proof organizations are feeling the need without knowing how to name it. Soccer named it years ago: the midfielder that scores few goals or assists but covers more surface area than anyone else, and now you see players wearing those cute little GPS vests under their jerseys.

Team sports and chess are games of strategy, where glue is essential. Organizations are messier than team sports and chess, which helps glue hide.

The generalist nature of the Staff line of work dates back to the original General Staff created in the early 19th century. The military formalized the distinguishing focus: line advances the core mission. Staff provides specialized support. Every corporation still uses this vocabulary today. I’m borrowing that from “From Hierarchy To Intelligence” by Jack Dorsey, legendary cultural anthropologist.

Chief of Staff is the most sophisticated organizational expression of an entire function that’s fundamentally different from line roles. Staff is more a way of life.

The world has spent decades optimizing for specialist depth. The rise of the Chief of Staff is the market’s correction.

The Chief of Staff title is often treated like a VIP access badge. Content is dominated by big, visible moments. Highlight reels.

But like all others, Chief of Staff is just a title. If anyone understands that most, ironically it’s the person who is drawn to the function for its generalist nature.

Chief of Staff content gravitates towards scoring goals or highlight reels, while glue work is ecological: the system produces both the problem and the solution. It happens everywhere all the time inside a system.

For every read of a board member’s face, there’s 10 reads of a non-board member’s face. For every founder and CEO feeling fuzzy, there’s 10 regulars feeling the same.

Both team sports and organizations measure goals, but only team sports measure surface area covered. Why not organizations?

Leadership runs through every work function. The glue role is fundamentally a support player, and calls for a different expression of leadership: from the back, like an elder elephant.

Anyone living this way of life would have an inexhaustible supply of micro-moments, measuring the surface area covered. Stacked on top of each other and the collection of micro-moments equals the board member’s face read, just at a different resolution.

Show me the elder elephants: the ones who dive into the mess with a junior and show a way out. I want to hear from the people who just happen to pop up when something is amiss, or ask that one question that clicks everything into place or recall that one thing from like five months ago that didn’t mean anything until that very moment. Talk to me about how you noticed someone else’s skill and positioned them to flex. The best feeling is when you orchestrate a system that knows something the parts do not. That’s the content I want.

The OKRs that performance baddies flex online serve a purpose, no doubt. But it’s the micro-moments of every passing day that define a company’s culture.

Culture is how an organization turns cause into effect and how the Staff function accomplishes the force multiplication it was designed for.

Once embedded into culture, it compounds and gets better over time, like a good balsamic vinegar.