What is your management operating system?

In other words, on a regular cadence, what do you do, how often do you do it, who do you do it with, and why do you do it?

For directors and above, this has proven to be one of the most revealing questions to discuss. It reveals their level of structure and organization. It reveals what they are truly responsible for. It reveals the level of detail they engage at. It reveals what they consider important and why. It reveals how they delegate to and trust others. It reveals their philosophy of how work gets done.

It also provides a structure for asking tons of related questions. “It’s interesting how little time Team X spends as a group, why is that?” “What’s the relationship between quarterly OKR planning and the monthly OKR check-in meetings?” “It looks like you’re only reviewing metrics monthly, can you talk more about that?” Any one of the pieces of this operating system is open to inquiry and discussion, as is the entire system and the relationships between the component parts.

Here, just as an example, was my operating system just before I left Squarespace: