Aaron Walter writes in a very good text about '7 Problems Growing Design Team Face'. I read this text as a support of what I wrote about in my post 'The problem with 'crash courses' in design thinking'.
The problems that Walter's discuss are all of a complexity and scope that is not possible to prepare for a crash course on design thinking. Anyone involved in real designerly thinking will always face fundamental questions that reach throughout an organization and has to do with organizational structure, people and processes. And to add on that, the diversity and complexity of values, visions and strategies.
This also means that any design challenge of importance will involve a team of people and that is when the issues that Walters describe emerge. Working together in a designerly way requires some common understanding of what a designerly process is. To just have a simple understanding of basic steps or phases, or of the importance of sketching or prototyping, or of iteration, is far from enough to handle these situations or the '7 problems'.
Designerly thinking is more foundational. It requires people to deeply understand the fundamentals of design, for instance what 'being in service' means or that design is about 'ultimate particulars' that require the design judgment more than any prescribed process model.