This paper describes a comprehensive, well-tested approach to managing residents with vexing noncognitive performance and attitudinal difficulties. Frustrations surrounding such cases often stem from inadequately defining and acknowledging the boundaries of faculty and resident prerogatives. Conceptual order is brought to these ill-structured problems by dividing nonroutine assessment into two cycles; a work-up cycle for suspected problems in which the resident is the primary decision maker, and a probation cycle for more serious issues in which faculty are the primary decision makers. By replacing adversarial positioning with a "let's find out" approach, the model encourages faculty to raise suspected issues early while supporting resident autonomy and professional responsibility. Finally, it recognizes the absolute discretion of faculty to judge trainee performance, to impose special requirements, or to terminate a resident's contract for cognitive or noncognitive deficiencies. Application of the model is illustrated through sample dialogues.