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Why is it that highly trained and seasoned executives fail? On the surface, this doesn’t make sense because they are very successful; yet research in the organization sciences provides no shortage of evidence to prove just that. From the classic Mann Gulch fire disaster of Weick’s famous collapse of sensemaking study, to studies of myopia of learning, escalation of commitment, threat-rigidity, dominant logic, the architecture of simplicity, the Icarus Paradox, to core competencies turning into core rigidities, and navigating new competitive markets using “old” cognitive maps, and many more such examples point to a ubiquitous phenomenon where highly trained and experienced professionals find themselves “stuck” in the heat of battle, unable to move and progress. On the one hand, for some, there is a desperate need for change, but are unable to do so, due to their trained incapacities. On the other hand, some simply cannot see the need for change, and continue with their “business as usual” mentality. For both, their visions of the world shrink, they have a tendency to cling onto their past habitual practices and oversimplify the complexity of the situation. In moments like these: DROP YOUR TOOLS and UNLEARN! This book chapter introduces a framework (grounded in clinical psychology) that has had consistent success in helping seasoned executives and key decision-makers open up the alternatives whenever they find themselves stuck with complexity.