How To Answer Difficult Questions

An interesting answer to a difficult question might not come to mind immediately… but you can usually make your answer interesting. Because what makes it interesting is not the answer to the question itself. It’s your unique take on whatever experience pops into your mind.

If I asked you…

Pete from Beard Strokings Avatar“What’s the strangest place you’ve travelled to?”

You might have trouble coming up with a good story to tell me?

You might have never left your home country, but you can MAKE your answer interesting. Perhaps you visited your aunt in the countryside and she made you shovel horse poo, and you realised you’re much more of a big city person than an outdoors person.

That’s not a very strange place to go, objectively. But the experience was kind of strange for you… and it made you learn something about yourself.

So what makes that response interesting to ME is that you’re sharing an experience, and I’m learning something about YOU.

Here’s another example answer to the question that I might give personally.

“Probably my trip to South Korea for 3 weeks while I was in college. The people there are so nerdy and disciplined, but when you get them drunk they’re like wild animals, because there’s so much pressure on them and they rarely get the chance to let loose. I kind of realised how easy and carefree our school life is compared to theirs, so I think I complained less after that. Also chicken feet are gross to eat.”

This isn’t a crazy story about a super strange place. It’s just what popped into my mind when you asked the question. I’ve definitely been to stranger places… I just can’t immediately think of any right now.

The point is that I shared something about myself.

Something I’d learned or realised or thought about… and you can connect with that.

Stop Searching For The “Perfect” Answer

It often trips us up when people ask us difficult questions with superlatives, like “strangest,” “best,” “most exciting,” “scariest.”

We feel like whatever pops into our head isn’t strange or exciting or scary enough, so we keep looking for the perfect answer. But this is completely counter-productive and prevents you from connecting.

If someone says “strangest place you’ve travelled to,” translate it to “strange place you’ve travelled to” and talk about the first thing that comes to mind.

And if that doesn’t give you any ideas, translate it to just “strange place” or “place you’ve travelled to,” or “strange experience.”

Then you can say, “Well I haven’t travelled there, but there’s this strange place I want to visit…” or “Well it wasn’t that strange, but it was pretty cool and I had this other kind of experience…” or “Okay it’s not a place… but I do have a strange story.”

Because I don’t care that you don’t have a strange place that you’ve travelled to. I care whether you can connect with me or not. Whether you can share something with me that makes me feel like I’m getting to know you.

That was the purpose of my question in the first place. It was simply an invitation for you to share something personal.

The beauty of this is that the next time someone asks me a similar question, I might give a totally different answer and not think about Korea at all. Because it’s not about the answer. It’s about sharing whatever the question makes me think of at the time.


So change the question if it’s too difficult… and focus on sharing something personal.

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