Jack Cohen demonstrates how to use AI for practicing difficult feedback conversations, showing a live example of addressing defensive responses. Jack starts with a carefully structured opening: “I want to talk to you about something that I’ve noticed in a few of our meetings… The reason I want to talk to you about this is I think there are ways we can make meetings more fun, ways we can reduce the number of meetings we’re having, and as a result, some possibilities we’re not tapping for being more impactful on our users.” The AI responds defensively: “I’m always open to talking about improvements, but honestly I think our meetings are fine. I don’t see the issue. Plus I’ve got a lot on my plate.” Jack demonstrates skillful navigation of this defensiveness. Instead of pushing back, he acknowledges: “You know, I’m actually glad to hear that. I’m not glad that you have a lot on your plate, but I think this can help with how much you have on your plate.” He then gets specific about the behavior while taking ownership: “I know that I can clarify what the focus of the meeting is upfront.” When the AI doubles down (“Maybe the issue isn’t with me, but how the meetings are structured”), Jack uses another technique - finding agreement: “Yeah, you make an interesting point. There are some structural things we could change… I don’t think it’s unimportant. I just think it’s a matter of priorities.” After the practice session, Jack asks for coaching: “I want to increase my feedback skill. Give me general feedback, as well as feedback on how I respond to defensiveness.” Jack notes you can practice in different modes: “Sometimes I do it in written mode like Tal did, which gives me more time to process. Sometimes I do it in voice mode because it feels more real, like a real-time conversation – I can feel it more in my body.” ➡️ Practice your exact feedback conversation with AI playing a defensive recipient. Get the wording right, navigate resistance skillfully, then ask for coaching on your approach - all before the real conversation happens. Check out Jack Cohen’s course (not sponsored, he’s just the real deal).