Every morning I take a couple of minutes to talk to him, make sure he knows where he's going and that he has the tools (technological and social) to get there.
About once a week, we have a wrap-up meeting to cover what we've accomplished, what's blocking us, and where we're going. This usually doesn't take more than 10 minutes and we'll skip it by mutual agreement if we both feel we're up to date and don't have anything in particular to talk about.
About once a month or so we have a 30-60 minute session over tea or coffee to just discuss communication at work, strategies, his morale, and how he feels he's doing in terms of happiness and making progress toward his personal goals.
Sometimes special situations come up through the course of work and we'll have impromptu sessions to talk about them as necessary.