It seems lazy. It is easier to repeatedly ask why than to come up with hypotheses and statements, but maybe this is just the difference between using the socratic method well and badly.
It seems condescending. Once you realize that your conversation partner is using the socratic method, the questions begin to seem pedantic and not genuine. It is particularly bad when I know the practitioner knows the answer to their question. If I don't know the answer, it is frustrating, if I do know the answer, it feels like we are wasting time.
I can't seem to break my colleagues out of this conversation method. Even after expressing that I don't enjoy it, they seem to genuinely feel that it is a better way to discuss technical challenges. How can I convince them otherwise?
The Socratic method has a time and place: symposia. People there were rich, well fed, drunk and came to converse and learn. People who come to the workplace are not rich, usually on a frustrating diet and need to earn money. Sometimes the one who has the information should just divulge it, especially when they don't have a formal mentor-mentee relationship with you.
> It is easier to repeatedly ask why
That doesn't sound like a proper application of the method. SM questions are guided and thus dishonest: the one asking already has an opinionated answer. Just chaining "whys'" doesn't lead to a useful answer, especially if you're already on the wrong track - more "whys'" will just derail the conversation further.
> It seems condescending
Everything consentual goes. It sounds like you're not consenting.
> It is particularly bad when I know the practitioner knows the answer to their question
Now we're back to SM. Earlier it sounded like your colleagues where not following SM (unguided whys'). That is a frequent and imho valid criticism of SM. To be fair, please keep in mind that it was invented in the infancy of philosophy. We have come two millennia since then. Your colleagues don't sound like very smart people.
> Even after expressing that I don't enjoy it
Changing topics from philosophy to labour law, that's harassment.
> How can I convince them otherwise?
Talk to your manager.