You already gave the answer yourself. You need to reflect on the topic beforehand. Something that is truly brand-new, you probably got some notification ahead of time that would have allowed you to do thinking prep. Things that are much more relevant to what you're working on or your business might be much more ad-hoc, so then that means you need to be always trying to think deeply about the work that you do and understand and evaluating all the potentials that are available.

> But I’m terrible at coming up with questions during dynamic meetings. I find that I need time to reflect on topics before I can form a clear idea of what I need to ask.

The trick is to have a set of general questions handy for all situations. "What is the meaning of life", "Is there life after death", "little endian or big endian", etc? The same thing with jokes. Just have a few ready to use on any ocassion.

Here's a really weird option, no idea if this works for anyone but me, but: go for a run before the meeting. I've found it clears my brain of all the junk that's occupying it for a few hours, and lets me hone in on the topic being discussed. It's also a bit of a self confidence boost so I don't feel as anxious about whether the question might be perceived as dumb.

Pattern match —- ask yourself “what questions have been useful at similar points in similar meetings” and ask the context-appropriate version of those questions. (If they haven’t already been answered.)

If this comes up a lot, come into meetings with a checklist and go over previous meeting notes and outcomes for “good questions” and “questions you wish you’d asked” and add them to your checklist.