I have recently taken it upon myself to coach and help prepare editors on how to become better administrators. To do so, I have developed a four phase system (described in the introduction section) that helps to cover all the aspects needed and to discover strengths and weaknesses more effectively.
I will use this page as a glossary of questions and to update/keep track of new methods. Feel free to make comments on the talk page about this, and to suggest changes and additions.
Generally, the phases should be given in chronological order. Questions in Phases 1 and 2 should be given three at a time, while questions in Phase 3 should be given one at a time. After coaching several users, I have determined that it is best to limit the number of questions a user can respond to in one day. This allows the coachee to develop over time. I suggest a maximum of five questions a day in phases one and two, one section a day (including followup questions) for phase three, and at least a month for phase four (about 58 days if done fully). Of course coaching can be done slower than this and is more beneficial if conducted at one's own pace.
I will be implementing Balloonman's footprints strategy as well. This will come in phases one and four.
- Phase one deals with questions designed to let the coach know what the coachee's best contributions are, and what their general strengths and weaknesses are. (3 days minimum)
- Phase two is all about policy. The admin coach will ask several series of questions dealing with policy, or will give lectures or advice based on administration. They will then critique the coachee's responses and provide help in areas where the coachee needs it as shown by the responses. (17 days minimum)
- Phase three has to do with Wikiphilosophy (inclusionism/deletionism, orthodoxy on Wikipedia, etc.). The coach will ask several questions about Wikiphilosophies and controversial areas of Wikipedia policy. (11 days minimum)
- Phase four is a phase in which coachees explore other areas of editing and areas that they may come across as an admin. The coach will provide minimal guidance in this phase, and should only answer questions rather than pose questions to the coachee. (approximately 30 days minimum)