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It’s entirely situational.
I feel really uncomfortable receiving criticism, but that is mostly a me-problem. While you’ll probably get along better by being nicer about it, you’re not obligated to walk on eggshells with anyone. Some strategies if you do decide you want to try and soften the blow anyway are the “compliment sandwich” and being constructive/improvement focused rather than dwelling on what went wrong (exampe: “here’s how you could improve this…”). Hope this helps.
Sometimes you don’t. Sometimes you ask yourself if it’s necessary to give the person criticism. You also ask yourself what kind of power imbalance exists between you two. And you also ask yourself if this person truly needs to be part of your life.
Context needed. I’ve never been in a situation in which I felt a need to give someone constructive criticism at random.
It depends on the person and the issue. Some things don’t need to be said. Some things do need to be said, but in the right way.
I straight up say things exactly as it is cause one way or another they’re going to overthink my words and be reminded of it by their own brain when they see the exact same pattern I had told them. Once the information leaves my moth I am no longer responsible of how the person interpret it, it’s on them.
You call them out anyway.
“Handle with kid gloves” I believe is the term. I would approach them with the things they did right first and then give my thoughts on how the other areas (that need improvement) can be improved.
If it’s feedback that you feel is important and necessary to share, and you want it to be received constructively, you can try reshaping the delivery so it’s not delivered as a criticism.
You don’t unless you absolutely have to. As I’ve gotten older I don’t bother criticizing someone like this unless it’s severe. It’s nit because I’m a pushover it’s because it’s not worth my energy.