Designing documents, such as writing a technical paper, manual or WWW home pages, starts with a goal in mind but often does not simply proceed in a top-down problem solving style. The document design process consists of a cycle of interpretation, modification and understanding. It requires both generating parts (words, sentences, and paragraphs) and structuring them while exploring what to write. Our research aims at supporting this collage or trial-and-error style of writing as design, drawing on the concepts of re ec- tion in action and hermeneutics. We propose representational talkback", which is feedback from intermedi- ate situations that emerge during writing. We postulate that by providing writers with appropriate representations to amplify this talkback, we enhance their writing process. This paper presents a theoretical framework of our approach and reports a user study using a prototype system ART (Amplifying Representational Talkback) to understand what types of talkback are necessary during writing and possible representations for them.