Erik has written a bit about his approaches in the past [1] and Graham [2] and I [3] are both currently trying different ways of visualising pains the teams have we are working in.
[1] http://erik.doernenburg.com/2009/11/making-build-pain-visibl... [2] https://github.com/kuona/kuona [3] https://github.com/cburgmer/buildviz