My first three years, I always dreaded the observations as I saw any shortcoming as a failure on my part. I'd often find myself prepping the "perfect lesson" to line up with the official meeting in order to show I was both cutting-edge, but also traditional in my approach with proper pedagogy. They all went decently...but I never really felt thrilled by any of them. When you know you're being fake just to be judged, you don't learn about yourself, and your bosses don't really learn anything about you.
The past two years have been a little different. With my newer/alternate method of teaching, I've found myself being less apologetic about my strategies. Since, I'm not just copying the curriculum, or strictly sticking to material inherited from others. By showing off materials and plans I've made personally, I feel much more comfortable with an administrator stopping by. They could stop by any period if they're like...my door is always open. In fact, I'd say I'd almost prefer it as it would give me a chance to show-off and talk about my tinkering with other professionals. Rarely are students "impressed" or critical, so it'd be nice to have a real conversation with another adult. My pre-observation yesterday went very well; it wasn't so much a conversation about me, but about teaching in general. My principal and I both sent ideas back and forth and I think we both felt we gained something from the conversation. It's a big change from three years ago.
But like I said...it's once a year. Due to union rules, state regulations, and other obstacles (mainly time), I'm only given feedback and conversation time every 180 school days. I'm not sure I really want to be judged more frequently (if you watch anyone long enough, you're bound to find plenty of flaws) but I think I'm at the point where I wouldn't mind it. In fact, having more observations would de-stigmatize the sole annual observation making observations more instructive and less punitive. Teachers are always complaining about never being treated like professionals, and others are always complaining about teachers never being held accountable...maybe a few more observations would solve this problem. Unless you're a car or a cavity, getting checked once per year doesn't do much good.