The problem of retention of college students who are under prepared for the academic demands of college will be addressed by looking at the skills and needs of "high profile" or high risk students. I will use critical and creative thinking concepts as a framework for defining relevant skills and motivation, and I will present an original model for developing structures for transformational dialogue to occur as well as offer suggestions for how to measure change through observable student actions. In this way, student needs and skill development can be assessed more effectively and authentic learning formats can be woven into the fabric of holistic outreach interventions.Contact cct@umb.edu for access to full text