Constructive Feedback to the Boss
I have never found this to be a successful or productive endeavor. Unless the boss's behavior is immoral, unethical or illegal, I have found that no matter how tactful or constructive the feedback these communications usually do not go well.
This is an obvious testament to the vocational endeavors I have pursued, coupled with the industry's typical leadership style.
I’ve had bosses in the past that no matter how good constructive feedback was, it was not taken well and nothing would change.
I have a boss at this time you can take constructive criticism to, with a suggestion on how to improve. I find he has a very open mind. Several times after constructive debate we have agreed on a good compromise.
As said by Carrie Stinson it depends on the boss.
I think it depends on the boss and how receptive they are to receiving feedback. It is true that professionals who have a high level of experience and who have worked their way to upper level management may not feel that a direct report has any business telling them what to do. However, the feedback may not be presented clearly in regards to how something their boss is doing is affecting their personal or team's performance. I also would say that any leader who is doing something illegal or unethical is going to be receptive to any feedback from a direct report.
I have actually had a little success in this area. I find that when I come prepared, approach in a more casual manner, and then explain the effects, I have no problems in at least being "heard" by my supervisors! Whether or not anything changes is a different story, but I do feel at least a little better having been heard!
TB