How do we model and improve technical problem solving, such as network subnetting? This paper reports an experimental study that tested three hypotheses, two derived from Kolb?s experiential learning cycle and one derived from the advance organizer technique. The two hypotheses following Kolb?s cycle were supported, and the one based on advance organizers was not supported. The results indicate that solving network subnetting problems starts concrete, becomes more abstract, and ends concrete. The lack of support for advance organizers indicates that they are not a good fit for technical problem solving, or that they need to be designed differently for it. We draw some implications for research and practice. We also call for additional research to extend Kolb?s cycle to other knowledge intensive problem solving domains.