If you have a question, just ask it. If you want to have a 5, 10, or 30 min, discussion, ask for that.
I'd prefer a long form question with all the communication from your side fully expressed, then I can ponder on it and multiplex it between my dozen other things.
Still.. the question is out there. At least when it's written out, you can know if it's a worthwhile question. Or ask some quick follow-ups that they hadn't thought to nail down first.
And as a blanket rule of thumb, don't send people chat messages that you wouldn't want to see displayed to an arbitrary meeting full of people. :)
Niceites are, well, nice. They help to make sure everyone remembers we’re all human beings rather than question answering machines, but we are also talking to get a job done. Unless you’re actually a good friend of mine if you drop me a message asking me how my weekend was, I know that you’re just lining up to ask me a question, but now I have to do The Dance to work out what it’s going to be about, whether I have time for it, and if I’m even the right person to ask.
> Them: "Hi"
> ...
> Me: "What's up"
> ...
> Them: "Do you have 5 minutes to join this conversation?"
> ...
is awful.
1) He/she is in a meeting, they have a choice - to or not to reply
2) If their screen is shared, I am not disturbing the meeting attendees making them read what I typed, and what comes in the notification pop-up
3) Gives enough time for the other person to switch context
4) Ignore me for an indefinite amount of time and continue their work
If the other person responds, my second comment would be with full details.