i've been a manager for about 14 months now and the feedback conversations still make me sweat. i was a good IC because i could do the work. now i have to tell someone they're not doing the work well, and somehow also keep them motivated and trusting me. nobody taught me how to do this.
here's what i've actually landed on after a bunch of awkward conversations:
be specific about behavior, not character. "your last three PRs had no tests and two of them broke staging" lands differently than "you're not being careful." one gives them something to fix. the other just makes them defensive.
say what you need to say in the first 90 seconds. don't warm up for five minutes about how you value them and then drop the thing. they sense it coming and spend the whole warmup period anxiety-spiraling. just get to it, kindly but quickly.
ask what's getting in the way before you assume they don't care. three times i've had this conversation and found out there was something real happening: a health thing, a scope confusion, something at home. not always. but enough to ask first.
write it down after. for both of you. a one-line recap email or a note in your 1:1 doc. "we agreed you'd add unit tests starting next sprint" is just a reference point, not a paper trail for PIP. but having nothing written means they can misremember it and you can misremember it.
the thing that still trips me up: when i can feel the person is hurt. my instinct is to backpedal and over-soften. but that actually makes it worse because then they don't know what they're being asked to change. i'm still working on this part.
anyone who's been doing this longer: do you find it gets easier with the same person over time? or does it depend on the person?