Tonight was one of those evenings when everything seemed to 'click'. I was fairly pleased with the gesture and proportions. I managed to get a decent indication of the values too, rather than getting too niggly with the contour - which is the trap I usually fall into.
I generally work sight-size (various sites listed under "Resources" give a good explanation of what this approach entails). My procedure starts with marking the top and bottom of the figure on the page. I then try to find the gesture by looking for a "rhythm" or "movement" which describes how the weight of the figure is transferred through the pose. I mark this with a flowing line through the length of the figure.
I then try to mark in the tilts of the main masses of the torso, before working on the contour (ie the outline). For me this is the part where I start to get too fiddly. The contour is not really the most important part of a figure drawing and it certainly doesn't need to be tackled in any detail at this fairly early stage. A better approach is to leave the contour and start looking for the shadow line. From where I was sitting, most of the pose was in shadow, save for a couple of places on the shoulders and arms.
I usually don't get much further than getting the shadow pattern massed in. Very occasionally I'll get to the point of being able to put in some indication of the background and start work on the halftones and modelling. Tonight I didn't, but I'm still fairly pleased with the results.