Using systems that work isn’t necessarily rigidity; it’s just smart! When you're at the same theater, with scores of full-time staff, and your cast and SM team are the main source of turn-over, it makes sense to use the same proven methods. Interns/apprentices may have to adjust to your style if it's not how they were taught, but they may find your ways click for them in a way others don't, so going with what's comfortable for them isn't always doing them a favor.
I find that freelancing definitely keeps me flexible, but I don’t consciously change my style, since in my mind style is mostly about personality. An example of style might be that I never yell at actors, I try to keep things positive, even when telling them things they don’t want to hear. My priorities do change though, to meet the expectations of the theater or director. How soon we use props, or take line notes, or tell actors they’re blocking is off, are based on the director. Who communicates crew call times, leads production meetings, or schedules the design run, can vary by theater.
The ways I use my team, beyond the basics of coffee making, sharp pencils, and copies, is based on the strengths of the people involved. Some people just aren't as good at pre-sets or handling script changes. But I do expect that if I give someone a project, it will be done unless they tell me otherwise. I expect them to ask me questions if they don’t understand, rather than just moving forward blindly. And there are probably a dozen little things I'll ask of my team, couched in phrases like “just humor me..,” or “I’ll sleep better if…” or “this sounds crazy, but please” that I’ve learned through experience just work better a certain way.