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We describe our experience of trying to develop a novel application that transforms information management (both coordination-based and personal) from stand-alone resources into resources deeply embedded in email. We explored two models for accomplishing this goal; these were to embed these resources in the email channel and to embed them in the client. Our exploration of the first model was intensive, in-depth and ultimately unsuccessful in large part due to our design process. We adopted Extreme Programming (XP) as a means to explore our second model more efficiently. This paper describes our motivations and experiences while exploring our first model before XP and then the advantages and disadvantages of turning to XP in the exploration of our second model.