Well, it is this exact question that got me interested in the topic. The answer to your question is, “we don’t know.” The research in this area (strategy implementation) is still in its infancy, and there is even less research on the “barriers to strategy implementation.” One possible explanation is that organizations are extremely social complex entities–at least this is how I perceive them. Therefore, organizational actors, systems, processes, policies, structures, and cultures are interrelated and interdependent. It seems many business leaders do not recognize this complex and systemic nature of their organizations. Companies invest huge amount of resources in developing strategies, but they don’t seem to spend enough time thinking about “what could make these strategies fail.”

By the way, thanks for introducing the phrase “advocatus diaboli” to my vocabulary 🙂