Hmm.. this reminds me of a design presentation I saw a while back that talked about using the "6 Thinking Hats" approach. Basically, after creating a number of designs, a facilitator walks team members through six different ways of thinking about a design. I guess it covers the same ideas as "walking both sides of the street", but it was suggested that 6 hats is easier to apply when dealing with non design personnel.

Quick googling got me this page: http://www.idspace-project.org/index.php?option=com_content&...