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Representation determines how we can reason about a specific problem. Sometimes one representation helps us to find a proof more easily than others. Most current automated reasoning tools focus on reasoning within one representation. There is, therefore, a need for the development of better tools to mechanise and automate formal and logically sound changes of representation. In this paper we look at examples of representational transformations in discrete mathematics, and show how we have used tools from Isabelle's Transfer package to automate the use of these transformations in proofs. We give an overview of a general theory of transformations that we consider appropriate for thinking about the matter, and we explain how it relates to the Transfer package. We show a few reasoning tactics we developed in Isabelle to improve the use of transformations, including the automation of search in the space of representations. We present and analyse some results of the use of these tactics.