As I read it something circled back to remind me — we can slice and dice culture all we want. In the end, there’s a simple test: is play tolerated and even encouraged? The classic real-life example of this is Zappos: http://twurl.nl/z74spu (be sure to check out at least one of the videos).

In reviewing two of the books written by leading voices on the topic, I too noted that there were key issues that were missed http://totalexperience.corante.com/archives/2010/02/28/design_thinking_in_stereo_martin_and_brown.php

Neither author sufficiently addressed:
1. The design question: At some point, after all assumptions have been questioned, you have to determine if you’re asking the ‘right’ question. Clearly cultures that are not willing to challenge the ’status quo’ will never get to the ‘right’ question. The conditions required for shared cultures that would allow for such behaviors is deeply addressed in the book “Theory U”.
2. Finding and embracing failure: Cultures that seek to portray perfection are not comfortable looking for failures as ‘food for learning’ (there’s a whole other conversation to be had around the significance of a ‘learning culture’ as purported by Peter Senge, see esp. “The Dance of Change”).
3.Embracing dichotomies: Design is about making choices, about accommodating constraints and deciding how to address them. Many cultures are “Black and White” — such cultures miss the variety possible in shades of grey — embracing the black and white at the same time (look for readings on “paradox” especially Charles Handy’s “The Age of Paradox”)

Already part of my Design Thinking approach is ‘honoring reality’ — it’s the part that comes after the ‘appreciative inquiry’ (which is part of both the research and discovery phases of Design Thinking). This and other perspectives required for successful Design Thinking are fed by all of the readings above and more. Particularly when the focus of the Design Thinking is on redesigning the organization itself, another book to add to the list is Russell Ackoff’s “Re-Creating the Corporation”.