I don't think being a seasoned pro helps with a lot of the riddles. There's been so many times when I've been given the solution and just responded with
Some examples:
Judi Dench = Bench
Tip your wings = Bank
I can't think of any more off hand
It's just a case of stepping back and seeing if anything fits. One person might go fifty times and still not see it, where as another person may visit once, and realise the clue immediately.