Good upper management avoids surprises and keeps managers in the loop on what we are doing. The amount of context we think we are over-communicating is usually the right amount.
In a work context, surprises are generally not great. The general rule is not to throw anything to your manager that catches them off guard.
Thus, we need to keep our manager in the loop on what we are doing and what decisions we are making. We should proactively give the right amount of context. From our perspective, it may seem we are over-communicating, but usually it is the right amount, especially when working remotely.
Lenny gives an example of how he sends a weekly update to his manager titled "State of Lenny" with three sections:
- His current priorities.
- Blockers he needs the manager's help with.
- Things on his mind currently that week.
Wes Kao also mentioned that we can structure our communication so that someone who already understands it can get the gist and someone who doesn't can continue reading through asynchronous communication.