The best leaders make it easy to bring them bad news early, when it’s still cheap to fix.

Problems have a price that rises with time, and the main thing deciding when you hear about one is how the last messenger was treated. If bringing something up early is uncomfortable, people wait, hope, and hand you a much more expensive version later. Ease of reporting is a design choice, not a personality trait.

Make the early report boring: ask what is going badly as a routine question rather than an alarm. When someone answers honestly, fix the thing and say nothing about how long it took them to say it. Do that twice and the timing improves on its own.