Rule 20 of 21 · Chapter IV — Losing Well
Choose the awkward conversation over the tidy silence every time.
Why this rule exists
Silence feels like kindness and functions like neglect — the problem keeps growing while the person keeps guessing. What goes unsaid gets filled in with the worst available interpretation, usually about you. The awkwardness is a one-time cost; the silence compounds.
In practice
When you notice yourself hoping something will resolve itself, treat that as the signal to book the conversation this week. Open with the thing you are avoiding rather than circling it for ten minutes. Say the sentence you rehearsed in your head, and then stop talking so they can respond.
When it doesn't apply
Some things are not yours to raise — private matters that do not affect the work, or another leader's territory that you should route to them instead. And if you are currently angry, wait until you can have the conversation rather than perform it.