I've worked in the UX field for several years, working in a range of skills from usability testing to user research to wireframing. I'm not nitpicky on the job title - I consider all of these "UX" related jobs. What I have found in several jobs is that the manager of the team (or sometimes just me) is not very familiar with HCI, usability, information architecture, etc..."familiar" in the sense that they have done this type of work and are now managing people who are have those types of jobs. Not having a true UX manager has had the effect of my learning about design and how to make good UX decisions through somewhat painful processes of trial and error. Each time, it's like I'm starting over again and again.
So, I'm wondering if having a manager who's been there/done that already is even important at -- and if so (or not) what types of questions can I ask to help me figure out if this is the type of place or manager where I can learn and grow, or if I'm just back to starting out again?