The article illustrates some of the strategies we are developing in the secondary analysis of Timescapes data and seeks to draw some general lessons for qualitative data analysts. We focus on three different areas of work. Across all of these we examine the potential explanatory value of working with data in a comparative way, and engage with some challenges presented by contextual specificity in the way qualitative data are generated. In the first area we consider the issue of how we situate qualitative data with reference to diversity across the population, and use an example of working between a single qualitative Timescapes data set and survey data. Understanding how qualitative data are situated offers a framework for internal comparison which maps onto wider diversity. In the second area we consider the outcome of bringing together primary researchers whose comparison of project data, as secondary analysts, allow them to ‘hear silences’ and, therefore, re-interrogate their own data within a revised conceptual framework. In the third area we describe how, as secondary analysts, we have worked across Timescapes data sets. Here we consider the challenges of undertaking secondary analysis across diverse, project specific, research contexts, and the potential of comparative working across data sets for enhancing understanding.