How do you stop yourself from giving textbook answers to messy problems?

It is so easy to fall into expert mode and just blurt out the most precise answer without checking the context. Most of the time, people do not need a complex technical breakdown they just want a quick workaround that fits their current mess.

When I am on the receiving end of those perfect answers, it honestly just makes me feel more stuck.

Do you usually ask follow-up questions right away or do you try to guess what their actual bottleneck is?