For the Ford Motor Company and the United Automobile Workers Union, fifty‐six pivotal events over three decades add up to a transformation in organizational and institutional arrangements. Compared to much of the literature on critical moments, which involves micro analysis of turning points in a single negotiation, this is a meso and macro study where deeply embedded cultural assumptions were “on the table” and, where effectively resolved, constituted an organizational or institutional pivot. Many pivotal events were planned, either as part of a formal negotiation or a large‐scale change initiative, requiring intentionally orchestrated critical moments. Others were unplanned and called for improvisational critical moments. The pivotal events also included situations where transformative potential was present, but the results fell short of the potential—a circumstance (noting what could have happened, but didn’t) that is not usually documented in the literature on critical moments. Not all critical moments in negotiations result in a pivotal event, let alone an organizational or institutional transformation, but this paper documents ways to connect the dots across these micro, meso, and macro levels of analysis.