We all know how much safer you can feel when you have a knowledgeable waiter/waitress. I will be explaining the things to look for by telling you about one of the best servers I have had in my life.
The first hint that your servers are really knowledgeable is if they have an immediate recognition of what celiac is. For example, when I mentioned to Maggie, my waitress at Zaytinya, that I was celiac, she immediately acknowledged that she was familiar with celiac. Maggie mentioned that her sister had extreme sensitivity. She told us about the food items on the menu that possibly could be cross-contaminated and which items we should order instead. For example, Maggie said that the flatbread was very crumbly and would get everywhere and that she would let the kitchen know to not bring the bread to the table. I didn't even have to tell her about cross-contamination!
She then told me how to find the gluten-free items on the menu and which items the chefs could convert to gluten-free. She also gave us her recommendations on what she thought were the tastiest options.
Additionally, she offered to give me a plate of cucumber and carrot slices instead of the bread so that I could put the hummus and other spreads on something flat. She also checked in on us often to make sure that I felt comfortable with the food.
Another good sign for servers is when they are willing to answer all of your questions and don't get annoyed. In Maggie's case, she anticipated all the questions I might ask about the surfaces and grills that could cause cross-contamination.