Complex domains require cognitive work for which current approaches to training may be ill-suited. To improve training for cognitive work, Klein and Baxter have proposed Cognitive Transformation Theory (CTT), a learning theory that characterizes sensemaking processes as essential to the development of expertise. The objectives of this research were to compare CTT with the instructional strategies of two expert air traffic control instructors to evaluate the relevance of CTT’s four teaching practices, propose refinements to CTT, and identify potential instructional strategies to serve as guidance for the application of CTT. Data were collected using cognitive task analysis methods, including course observation, artifact examination, and knowledge elicitation with two instructors and seven of their students. Data were coded using categories derived from theory and patterns emergent within the data. Results suggest that many of the instructional strategies used were consistent with the teaching practices of CTT and that learning was aligned with the active sensemaking claims of CTT. An integrated set of instructional strategies and a few refinements to CTT are advanced to further its application to training in complex domains. Although this set of strategies may benefit current training practices, further research is needed to evaluate their effectiveness.