I had an interview two days ago… One of the questions stumped me.
The manager asked "Tell me about some challenges you've faced."
Now, I know from reading Ask A Manager (AAM) that the subtext is "work challenges that can be related to the position we're talking about." So, even if I broke my toe and yet needed to climb a mountain to rescue an old granny and her dog before they were evicted, that isn't what he's looking for…
Also from reading AAM, I know that I should not bring up any interpersonal or political issues, and most of my "challenges" over the years have been interpersonal (manager interaction).
And, finally, I'm a typical introvert; we need time to think. This wasn't a question I had prepared for because it wasn't a question I expected. Maybe that surprises you, but it wasn't a question I'd been asked before.
To stall for time (and get context), I asked "First, can you tell me how you define 'challenge'?", But he replied "How do you define 'challenge'"?
A difficult situation that you overcame?
Think, think, don't take too long, think…
I came up with a situation early in my last job where a project prompted me to try a new tool and use it to build a solution. (Growth! Ingenuity! Not doing things the traditional way!)
And then he asked for another example. Gack.
I dug around and picked a time when I was asked to work part time with another team. He asked what made that a challenge. (I bit my lip (metaphorically), did not say "Seriously? You have to ask?", and came up with an answer.
If he had asked for a third example, I had nothing.
Two and a half hours later, at home, I still had nothing. I realized that my biggest challenge was in trying to come up with responses to the "challenge" question.
Is this the new "weaknesses" question? Is there a recommended way to answer? Should I rethink my definition of "challenge"? Should I just hope no one ever asks this question again? (That's actually not an unreasonable hope.)
I solve problems for a living. It's what I do.
I don't think of these as challenges; I think of them as my job.
"Normal" isn't a "challenge".
Still, there may be hope if I rethink the definition I had in my head. I looked up definitions of "challenging" last night. (Aside: don't look up "challenge"; the definitions and connotations don't work).
I found these two:
testing one's abilities; demanding
difficult in a way that is usually interesting or enjoyable
If I combine those, I get testing one's abilities in a way that is usually interesting or enjoyable, which describes most of the projects I've worked on. That could give me a wealth of stories.
Unless I'm asked "what made it a challenge?", I might be all right with this plan. If the interviewer has a different definition in his head, will he allow "it was something I'd never done before" as a "good enough" reason? Or will he worry that I'm equating "new" with "challenging"? I don't think managers want people to think that way.
Should "challenging" be unusual?
Am I over-thinking this?
vlbrown-mzydt 
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