Scholarship on life cycles of teacher development posits that teachers progress through specific stages with specific developmental needs. However, this scholarship rests on studies over traditional ten-month, semester, or quarterly education cycles and does not accommodate alternative teaching frequencies or durations. This study applies this literature to military instructors teaching a two-week course, twelve to fourteen iterations per year to inform faculty development. It finds that instructors develop according to the number of iterations taught, and it also identifies the parallel formation of a team identity. Both of these timelines can be accelerated through targeted developmental events to enhance teaching effectiveness.