Timing is Everything

Never give upward feedback when your boss is stressed, rushed, or in front of others. The best moments are:

• During scheduled one-on-ones — the expected forum for honest conversation
• After a win — success puts people in a receptive, open-minded state
• When they explicitly ask — be ready with honest input for these moments

Avoid Friday afternoons, the day before a big presentation, or any moment when your boss is visibly under pressure from above. Context decides whether the same words land as helpful or hostile.