When we cannot glimpse the landscape ahead from a superior vantage point, it creates feelings of uncertainty. The recent US Presidential election, which initiated a leadership change, means many social sector organizations will face an altered landscape to fulfill their mission. A complete rewrite of a strategic plan is perhaps too much work or inappropriate at this juncture. Perhaps a scenario panning session might offer a productive output. Several enterprises used scenario planning during the pandemic when the rules were unclear, and long-term viability remained obscure. One of my favorite models is the Six Thinking Hats from Edward de Bono. I appreciate that only some ‘hats’ (mindset) will resonate with our key attributes, but completing the process delivers a holistic experience. Generative conversations can replace fear and unknowing with alignment and increased clarity.