To answer this question, it’s important to know that every situation is different. Every company is different. Every individual is different. What’s not different is how long you should wait to deliver feedback, especially if it’s critical and difficult.
Give the feedback as soon as you can.
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Rip That Band-Aid Off
Giving feedback is hard. Giving critical or constructive feedback is even harder, but don’t overthink it. Yes, it’s important to approach the feedback with empathy and think about how to say what you want to say, but don’t let it get in the way of delivering the feedback.
Put yourself in the other person’s shoes. If I was doing something incorrectly or poorly, but didn’t find out for a month, I would feel like an idiot! (That has actually happened to me). I was embarrassed that I’d been doing something wrong for so long and lost trust in my manager for not telling me sooner. We eventually patched things up, but it made me worry I was doing something poorly without knowing.