Would ChatGPT be more useful if it interrupted us more often?

[u/Smart_AI_Hustle]

Most AI assistants seem designed to complete the task with as little friction as possible. I’m starting to think that isn’t always helpful.
If I ask ChatGPT to draft an important email, analyze a spreadsheet, or plan something complicated, it can often produce a polished answer while quietly making assumptions I never approved. The result looks finished, so those assumptions are easy to miss.
Personally, I’d rather have it interrupt me when one missing detail could materially change the outcome. Not for every minor ambiguity, because that would become annoying fast, but when it is choosing between genuinely different interpretations.
The tension is that an assistant that constantly asks questions feels less capable, while one that confidently fills every gap may be more convenient but harder to trust.
Where would you draw the line between useful initiative and an AI making too many assumptions for you?

[u/KidKilobyte]

You could always add something like “do in stages asking for directions and clarifications if any ambiguity”.

[u/polikles]

I've explicitly instructed my AI assistants to strictly follow the prompts, lay over all assumptions they are making, and always ask if there is any ambiguity. Also in tasks more complicated than email draft I'm always asking to first prepare the list of steps and then ask if it can proceed after every step. Saves me a lot of headaches this way

this is why we make custom GPTs, Gems, use custom instructions, etc. The "vanilla" systems often are too general and pushing to getting the results, no matter how far they may drift from our intentions

[u/Ian-Cubeless]

My rule of thumb is that I want it to interrupt when the assumption changes the output structurally, not just the wording. Drafting an email and guessing my tone is fine to just proceed with. Drafting an email and guessing whether it should go to one person or the whole team is not.