This article reports on the theoretical and empirical development of a four-stage model intended for developing management cognition in the area of creative problem solving that was piloted with a doctoral student who holds a managerial position in a college. Using a single subject case study design that employs experience sampling methodology, the models flips the order of the teach-then-assess approach: Stage 1 examined the student’s approach to solving problems at work through collecting two weeks of survey responses on her smartphone at work. Stage 2 scaffolded the student’s approach to creative problem solving with a focused discussion of research on the role affect plays in problem solving. Stage 3 gave the student time to reflect upon this research by journaling for five days, followed by a discussion with faculty members. Finally, Stage 4 repeated examining the student’s approach to problem solving through a survey on her smartphone and presented the student with an analysis of the two rounds of ESM data, and how it differed depending on solving a “new” versus “prevalent” problem (i.e., Stage 1 & Stage 4) and her journal entries. This time she derived new ways to solve organizational problems. Student data from these four stages is compared to extant literature and analyzing creative problem solving practices with real-time data collection methods is discussed