There is a growing body of research suggesting that CAD does not, has not, facilitated the advances in designing that should by now be evident. The history of CAD is replete with claims that CAD improves designing and it is a common claim in the publicity of CAD vendors. However, the reality appears to be somewhat different with claims by Musta'amal, Norman and Hodgson (2008), Lawson (2002) and Walther, Robertson and Radcliffe (2007) that CAD does not in fact improve designing to anywhere near the extent that we would like to believe. This is particularly relevant in the context of Design and Technology. This paper investigates the reasons why this may be so by referring to the literature on designerly thinking (Middleton, 1999; Oxman, 1999; Newell & Simon, 1972; Schon & Wiggins, 1992; Suwa, Gero & Purcell, 1998; and Verstijnen, van Leeuwen, Goldschmidt, Hamel, & Hennessey, 1998) and then suggests a manner by which the designing of students using CAD can be enhanced through an alternative pedagogical approach applicable to Design and Technology (D & T). The results of a trial intervention aimed at testing this pedagogical approach will be presented.