I've done some freelance stuff, and I'm currently doing a PhD where my time is very much my own to manage. Consequently, I've got some experience of being on th

I've done some freelance stuff, and I'm currently doing a PhD where my time is very much my own to manage. Consequently, I've got some experience of being on the other end: being left free to my own devices, and occasionally having that backfire. Things that I think are important: * Give some small but significant (~week-level) milestones, ideally with tangible results. Then discuss these. * Check up with the worker. Not by asking vague questions about how things are going, but specific questions about stuff that interests you in their work. I once worked on three projects at once for a place. Two of them were going very well, but one of them was going very slowly because I was kind of stuck. Getting input from the boss on that one really helped -- but I'd never have asked him about it, because I reasoned he'd hired me so he didn't have to worry about it. * Help with any other stuff on their plate. Family issues, money issues, personal issues, etc. Obviously, you can't solve most stuff like this, but you can usually help. I once delivered a contract very late due to getting a wrist injury, and being unable to promptly see a doctor. * Try to keep a dialogue going about work. Whether you're happy with their performance, whether they're happy with your pay/conditions, etc. Crucially, if any of the above ideas seem like overkill, you'll find out about this, and dial them down accordingly.