Holacracy Community of Practice Archive, 2015-2019 Community Holacracy Web Site

Getting people to self manage is always a challenge unless they are naturally that way.
In my small business (8 years traditional, 1 year Holacracy)  I too have struggled with the temptation to "force" my people to practice specific habits compatible with self management. I'm the founder and lead link of our single circle organization. I end up doing most of the work anyway and getting part time staff members to see themselves as partners has been a frustrating process.
But in the end, I think the best way to engender the required internal sense of responsibility is to simply refuse to do their jobs for them. When they come to me for permission or guidance on a project that is their responsibility, I remind them that it is theirs.
I also sometimes allow my frustration to show. When I feel that they are trolling for reassurance from "the boss" or failing to properly plan and organize their projects, I let them know that Holacracy gives them the authority to make decisions in order to save ME time. I NEED them to take the responsibility they were given and to stop checking in with me for every tiny thing. I have my own work to do, after all.
I also let them know if I feel that their personal productivity system needs improvement. I reiterate the desired outcome and offer to coach them on their system if they need it, but I only insist on compliance in areas that interface with the rest of the staff. For instance, if a person has trouble being on time, I will remind them that timeliness is part of their job and ask if they need help with that. I insist that official In-boxes be regularly cleaned out; and if I notice that they tend to use their In-Box for storage, I will offer to provide other storage solutions for them. I insist that they keep their schedules available through our shared google calendar, but I do not micro-manage which hours they choose to be available to work. 
I also try hard to make the tactical meetings a safe space for anyone to broach any tension and to use the system to solve problems that otherwise would be left unsolved. 
I hope that helps a little. I'm sure it's different with a larger organization.