There are advantages to not being bogged down by bureaucratic change management systems. :)
Almost didn't vote you down because of the last part, but you seem to be moving the goal posts a bit. Oh, moving to new OS in a month! Bah, bah not possible. Move one server to a newer version of the same OS: Oh, I'll just let that run over night and no one will notice. If the scope of your server and applications is such that you can migrate it over night unattended, then hiring people with expertise to let management know what would be the best upgrade path is not "unacceptable". It would be the professional thing to do. Unless, of course, you were more worried about your revenue stream.