The motivation for this paper is the need of the German National Library to massively increase its web archiving activities as the 12,000 snapshots collected per year are considered not to be enough to reflect the German web appropriately. As collecting everything which could be defined as the German web is impossible, the concept of selecting an “exemplary diversity” is introduced and substantiated by the guiding principles of relevance and diversity. The long-term goal is to find methods to (semi-)automatise the selection process and the prerequisite for this are well-defined selection criteria and sources of relevant as well as diverse topics that can be exploited. First steps to operationalise the guiding principles are outlined and supplemented by technological challenges and requirements to support the selection process as well as in the light of the advancement of web technology. Finally, the paper proposes a mix of curational and automatised measures and sources of information that should be taken into consideration to cater for a good coverage of relevance and diversity, supplemented by technological aspects regarding alternative representations of web content in web archives to be discussed to bring the content of web archives closer to the original user experience.