Anytime I hear questions like "most challenging blah" I interpret it to mean "an interesting and challening blah". Don't get caught up in trying to think about the actual most challenging thing you did, just pick something that was difficult. Pick something you succeeded at in the end, and make sure it isn't boring: interesting is a key word here.
When I ask questions I'm listening for specific details as well. Describing in brief the full stack of an app isn't interesting. Pick a hard part and say what you did.
For example, when asked said question, I could respond:
I worked on a financial trading system. We had several computers spread across various exchanges and needed to coordinate messages on multiple networks. The user needed a UI that responded quickly with many instruments open.
yawn says nothing, compare to:
On a finance project we had a real problem with writing tests. Multiple networks, and erratic markets, lead to some absolutely crazy scenarios. I had no choice but to somehow simulate this world in our tests. This lead to a YAML+M4 driven domain specific language that could create exchanges, behave as a user, and simulate acausal network activity (yes, that actually happened!).
Started out teaching English at Embry-Riddle.
Graded 10,000 essays.
Lesson learned.
Became a mathematics teacher.
Discovered computing.
Never looked back.
Location
Houston TX
Education
Stetson University: B.A., M.A. in English; M.S. in mathematics
Anytime I hear questions like "most challenging blah" I interpret it to mean "an interesting and challening blah". Don't get caught up in trying to think about the actual most challenging thing you did, just pick something that was difficult. Pick something you succeeded at in the end, and make sure it isn't boring: interesting is a key word here.
When I ask questions I'm listening for specific details as well. Describing in brief the full stack of an app isn't interesting. Pick a hard part and say what you did.
For example, when asked said question, I could respond:
yawn says nothing, compare to:
M4, wow! (I never met a macro I didn't like.)