Cardinal social rule is to never make someone feel like an idiot. Perpetually have to assume that everyone is deathly afraid of being perceived in this way. Preempt the interaction by letting them know that stupid questions don't exist. Briefly jest about how they're already in a better position compared to when you were in their shoes. Slip in an anecdote about something embarrassing that happened to you with a level of unreactive casualness that indirectly signals to their brain that it's safe to relax. Chuckle in response to any semblance of an amusing remark. Liberally administer daps when you start to notice them entering conversational flow state