A graduate course required for principal certification was restructured to illustrate authentic learning in partnership with local school principals. In this data driven decision-making course, students, principals, and the professor collaborated on problem-based learning tasks. At the end of the course, the aspiring principals identified school instructional needs, accessed and analyzed district student data, and made decisions that were reported to the participating schools. The graduate students valued the experiential nature of the school-university partnership. They learned the difficulty of defining a feasible evaluation question and accessing appropriate data. These aspiring principals mastered the basics of two data analysis software tools. They became confident in using data and were convinced that more effective decisions can be made when clearly defined questions are answered based upon appropriate data. All graduate students admitted to initial trepidation with the unconventional ambiguity they dealt with, but overcame it with patience and practice to achieve an understanding of authentic learning.