Here’s a great question to ask in conversation with others, as a crowdwork question, or (to yourself) when writing bits:
So what was surprising about that?
In the real world, it’s a great way to trick someone into being interesting. Surprise is at the heart of comedy and interestingness; it’s showing us an outlier, something weird, and/or a break in a pattern.
In How to Write Usefully, entrepreneur and author Paul Graham explains why this question works so well:
So what's interesting? For me, interesting means surprise…When friends came back from faraway places, it wasn't just out of politeness that I asked what they saw. I really wanted to know. And I found the best way to get information out of them was to ask what surprised them. How was the place different from what they expected? This is an extremely useful question. You can ask it of the most unobservant people, and it will extract information they didn't even know they were recording.
Surprises are things that you not only didn't know, but that contradict things you thought you knew. And so they're the most valuable sort of fact you can get. They're like a food that's not merely healthy, but counteracts the unhealthy effects of things you've already eaten.
The trick is to use yourself as a proxy for the reader. You should only write about things you've thought about a lot. And anything you come across that surprises you, who've thought about the topic a lot, will probably surprise most readers.
Translated for standup: If it surprises you, it will surprise the audience. And surprise is key to getting laughs. A good punchline is one you don’t see coming.
Graham also wrote a good tip on the importance of being at least a little bit contrarian:
Let's start with a test: Do you have any opinions that you would be reluctant to express in front of a group of your peers?
If the answer is no, you might want to stop and think about that. If everything you believe is something you're supposed to believe, could that possibly be a coincidence?
Odds are it isn't. Odds are you just think whatever you're told.
Many great standup bits come from playing devil’s advocate/arguing against conventional wisdom. Combine these two ideas (i.e. be a contrarian in a surprising way) and you’re on your way to a good bit.