Sustainable development is a long-term endeavour involving deep uncertainty and requiring transformative change at multiple scales. To navigate such a grand challenge, new approaches have been developed in various academic fields, such as Policy Analysis and Sustainability Transitions. Two prominent approaches to strategic planning within these two fields are Decision Making under Deep Uncertainty (DMDU) and Transition Management (TM). While DMDU provides analytical concepts and tools to prepare for change (one that happens anyway, whether or not we desire it), TM offers a governance approach to condition change (one that we desire). We argue that the sustainable development agenda could benefit from an explicit cross-fertilisation across the two approaches. We will highlight the commonalities and differences between the two approaches and reflect on potential cross-connections. We argue that DMDU can benefit from the participatory process of TM, and its interventionist approach, which helps to mobilise actors and build networks for sustainability transformations. DMDU can also learn from some of the governance instruments offered by TM, such as visioning, experimentation, and social learning to better prepare for change that can only be dealt with through transformative actions. TM, on the other hand, can be enriched by analytical concepts and tools developed by and widely used in DMDU, such as tipping points and signposts, exploratory scenarios, and Exploratory Modelling, to operationalise transition pathways into actionable policy decisions. An illustrative example is used to demonstrate what a cross-connection between the two approaches might look like.