This doesn’t really fit with the topic of discussion but since this thread was derailed a while back I’ll respond. I had to read this a few times to see if it was serious… This sounds to me a lot like one of my favorite terms from another tradition " idiot compassion", ie compassion without wisdom. especially this part.
People are paid to perform a service and a supervisor your job is to supervise them in said service and make sure it gets done. Sure sometimes if a person is struggling you help them, and if you’ve fostered an open atmosphere of mutual support between the group you supervise, everyone helps each other in tough times, but There is a difference between being supportive and doing the work for the people to the point where they start expecting it and taking advantage of it.
This just seems to fall into the stereotype that practicing meditation turns you into mush, which in my experience does not appear to be the case, in my own practice and others I know. It has been my experience so far that peoples pre-monastic experience plays a very strong role in their monastic experience. I have used many if not all of the skills I gained in all I did in lay life so far while living at the monastery, and I believe these skills will serve me well in the future.
So I guess to tie it back, being a senior monastic does not automatically mean you know how to run a monastery properly, or how to manage others and foster positive environments, the same goes for working at a job, being promoted to supervisor because you’ve been there a long time does not mean you know how to be a leader.
good Leadership takes intuition, understanding(of human nature and more), flexibility, open mindedness, training, and experience. Being able to connect with those under you on a human level, but also maintain a level of authority and respect that is earned, in which people are willing to follow you for your qualities, not because of your position. Of course a person like this is an extreme rarity, but it’s an ideal to practice living up to.