I tend to to put a theming around a group of characters names. Like one group would be Crow, Raven, and Rook. And another group would be Tabu, Shadow, and Mistique. People who do plant magic are named after plants. Etc.
The weirdest one was trying to name the older sibling of someone named Nono. I was almost going to go with Sisi, as a bad Spanish joke, but it sounded too close to sissy. But ended up calling him Ottavo, because Nono means 9th in Italian and Ottavo means 8th.
I am not very good with coming up with titles tho, and I usually end up with something that just sounds off.