In my experience, which comes from both sides of the table, the two are not necessarily mutually exclusive. The fact is that servers have a vested interest in both making the customer happy, and in making the chef happy. Guests pay servers' bills, but chefs can make servers' lives hell! The customer is happy when he receives a meal that pleases his palate. The chef is happy when his food cost is under budget (a very rare occurence), but also when the dishes that he creates please the majority of palates. If the server gets the notion that your palate is not particularly developed, he will try to sell you whatever he has been told to, or whatever is the most expensive. But if your server has an idea that you have a sophisticated palate, he will steer you towards the chef's "babies"-- those dishes that the chef has lost sleep in perfecting, and that might well be gone tomorrow. I think the best approach for getting the best meal is to develop a sense of trust. On your first visit, you can ask the server which dishes the restaurant specializes in, and order one of those. These dishes are most likely to be "crowd pleasers", but if they are executed well, on the next visit you might ask your server what he would order if he were dining here that night. This is the question guaranteed to deliver the most varied and creative responses. My finest moments as a server were those when a guest trusted me to choose his meal-- I would consult with the chef, and all of us- customer, server, and chef- were always happy at the end.