Student staff members are critical to the success of student life divisions in higher education. Resident assistants, orientation leaders, and other student leaders are at the forefront of work with additional students. As such, their development and effectiveness in their roles are of the utmost importance. A specific tool and technique to foster development is the use of Individualized Accountability Plans (IAPs) that are grounded in the theoretical perspectives of Kegan’s (1994) Orders of Consciousness and Baxter Magolda’s (2004) self-authorship. IAPs help student staff and their supervisors co-create action plans to inform their work, and decide how each staff member will be held accountable. Co-creating a plan of this nature is a developmental practice of its own—akin to Baxter Magolda’s (2004) Learning Partnerships Model. This chapter describes the philosophical and theoretical background of IAPs, a process of implementing IAPs, possible approaches to assess effectiveness of IAPs, and recommendations to develop further the IAP process.