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I do what john suggested as well. Although for me I assign a mixture of bugs and projects with tasks to a bunch of developers. I have a special "not assigned" context for bugs that should be assigned to someone later on. I have noticed that if I assign too much on any one person, the speed of development slows down. If he is only working on a couple of things he can really focus on that and he knows Im tracking it closely and the task also seem more important. I have a folder for a particular milestone. I move projects and tasks out of that folder. I flag stuff that must be fixed for next release. Everything not flagged is desirable but not a must. If I notice that one guy is not in top shape that morning I might give him a couple of easy tasks that he can finish off in short time. That puts him into a flow and kick starts him so I can assign a tougher task later on. I am a bit sly that way perhaps but it really works. I assign using skype, email and just talking. I also play with on-hold contexts, naming conventions, "won't fix projects" and record a history in the notes section of each action item. I live mostly in planning mode for this. My approach has a lot of micro management to it but works well for me.