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Even with claude I have the issue that if I give it what I think an issue is it will tunnel vision on that. I'd appreciate more pushback when I am wrong when I am trying to work through a problem. Trying to add some uncertainty to the tone of my request can help but is often not enough.
If you want a partial solution:
I often write lengthy essays, which LLMs praise by default. I know that at least part of this is sycophancy. What I usually do is copy and paste it, but then claim that this isn't my work, it's something I found on the internet, and then ask for critique.
I suspect that something along these lines will work for you. If you want models that do relatively well at pointing out issues without you prompting, Gemini 2.5 Pro, o3 and now GPT-5-Thinking seem to be better than the norm.
My last experience with this was having it help me figure out a home repair issue. I am not handy at ALL but I thought I knew what might be wrong with a broken garage door opener, but only in a very general way and I was not sure how to effect the repair. It was able to help me get everything fixed through a mix of describing the issue and supplying plenty of photos, but everytime I gave my current guess of the state of the situation it would affirm me even though I was only right about 2/3 of the time.
Hmm.. I'm not sure what to do in that situation. My best guess is to plead utter uncertainty, and ask it to formulate the most probable issues in the order of likelihood.
Asking for a ranked list sounds like a great solution, sometimes it is wrong even when its not being sycophantic (which I don't mind its not magic and the information I am giving as someone with no clue what I am doing is imperfect at best) so that sounds like a two birds one stone kind of fix.
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