This thesis presents a toolkit that aims to increase cognitive proximity among strategic designers and senior decision makers. In keeping with the general aim of the research program CRISP - PSS 101, these tools aim to establish a shared language and shared understanding (overlap in mental models) among these disparate actors. Such sharedness is crucial in their collaborative efforts when developing new value propositions or when involved in strategic innovation. However, appropriate tools for heterogeneous network communication and collaboration at a strategic level appear to be missing. In addition, it is suggested that designers have an added value by providing senior decision makers with new frames that help them perceive their business environment as well as the strategic activities in a new way. A better understanding of, for instance, the social reality of their customers will help them identify latent needs, explore new business opportunities and develop new propositions. This yields two main questions: (1) how to support strategic designers in their interaction with senior decision makers to establish a common ground? And (2) how can strategic designers help senior decision makers develop new mental models of their business ecosystem? These two questions are intricately linked as they provide the ends as well as the means for interaction. The research takes an explorative approach, starting with developing a tentative conceptual framework of “what is going on”. This framework is grounded in preliminary observations and a literature study, which focuses on strategic thinking for dynamic business ecosystems (e.g. Product Service Systems) and theoretical concepts concerning social meaning-making like: cognitive proximity, mental models, sensemaking, frames and metaphors. The findings from this literature study are presented in a conceptual model and used to define a set of design guidelines that serve as the foundation for the design and application of the toolkit. The central premise of the design guidelines is formed by the concept of metaphor. Metaphors have the intrinsic quality to bridge communication and generate new understanding. This notion of metaphor is operationalized with a number of complementary concepts, like: causality, open-ended, generative, transferable, embodied and recognizable. The toolkit includes two types of artifacts: diagrams and three-dimensional objects (i.e. tangible). The diagrams primarily intend to support communication in one-to-one conversations or small group meetings, whereas the three-dimensional objects support communication in workshop sessions for larger groups. These symbolic artifacts (i.e. metaphors) are in fact the stimuli that prompt sensemaking, which consequently stimulates mental model development and generate shared understanding. The application of the toolkit is examined in a variety of empirical studies. These studies include interactions between Behzad Rezaei, a strategic design consultant, and senior decision makers from public and private sector organizations. The toolkit is deployed in the early stages of a client-consultant relationship to facilitate the first encounters between Behzad and senior decision makers. Most of the data was collected through observations during workshops and meetings. The observations focused on how the tools were used during the meetings and workshops and how they affect the interaction between the strategic designer and senior decision makers. Subsequently an evaluative interview is conducted to reflect upon the application of the toolkit and to concatenate the results of the empirical studies. The results show how the toolkit fulfills several roles to serve a variety of purposes: it facilitates communication, supports frame creation, initiates sensemaking, develops understanding and stimulates sensegiving. The toolkit not only increases proximity between strategic designers and senior decision makers, but once senior decision makers succeed in their sensegiving attempts, the toolkit also amplifies proximity between strategic designers and other organizational members. These results are analyzed through three lenses (i.e. dimensions): cognitive, physical and socio-material. The aim of the analysis is to extract principles that may contribute to subsequent research or tool development. From the analysis a number of principles emerge that seem to enhance the interaction between actors (i.e. strategic designers and senior decision makers, and senior decision makers and their organizational members) and their hermeneutic interaction with the world (i.e. business ecosystem). These principles include bridging metaphors, generative metaphors (i.e. analogies), memes, shared display, mapping, multimodality, transparency, coordination, reflection (i.e. perspective taking and making) and malleability. In particular multimodality, mapping and malleability seem fundamental for stimulating and facilitating activities like reflective conversational interactions, perspective taking and making, boundary crossing, strategic sensemaking and sensegiving. Consequently these activities promote the development and alignment of mental models in such a way that they help actors establish a common ground. Moreover, the principles portray two processes that form the answer to the key questions above. The first process involves the alignment of mental models to create cognitive overlap; it corresponds with the first question. It encompasses processes like coordination and embodiment. The second process relates to the second question, it concerns the shaping or development of mental models to increase their accuracy. It involves methods and activities like: (re)framing, sensemaking, reflective dialogue.