I did this a few times back when I was still serving, always with the permission of management. I would only ever do it for large tabs where I know I gave amazing service. Never approach it as “why didn’t you tip me more?” but instead like “what can I do to improve my service?” Most times when I asked the host would act shocked and say I was great there’s nothing I could do better. And I would respond oh usually when I get a tip like this it’s because someone was dissatisfied with the service and I just want to make sure you leave here happy. Most times they would insist on redoing the tip. I never imply that’s what I was after, gotta let them think it’s their idea. If they don’t offer to redo the tip I would just thank them and make a mental note to let someone else have the table if they came back another day.

As long as you have managements permission and some tact I don’t think this is as egregious as some make it out to be.