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Strategic management is traditionally seen as an exclusive managerial task rather than inclusive where accountability is reserved for top managers. However, contemporary strategy management practices increasingly pay attention to equality, diversity, and inclusion (EDI) by engaging with broader internal and external stakeholders via more open business models such as ecosystems. Hence, central to our examination is the concept of openness disposition, which in the context of strategic management refers to the tendency of individuals, collectives, and managers to make strategy transparent, participatory, and/or inclusive, or look for closure. While openness in strategy is regarded as a positive means of contemporary management, fostering diversity, creativity, innovation, and empowerment, there are some researched downsides too. The purpose of this chapter is to address the openness puzzle in strategy and gain a deeper understanding of the dilemmas of bottom-up strategy initiatives, and investigate the associated dilemmas, if any in the context of manufacturing small and medium enterprises (SMEs). We contribute to addressing the performative effects of the dynamic expansion and contraction in openness within the SME strategy process while using the concept of openness dilemmas, tensions, and disposition. Using the Management Control Theory, this chapter will combine theory with SME practitioners’ experiences of bottom-up strategy initiatives to increase EDI in their organisations. Based on findings that emerged from a four-year longitudinal multiple case study research with 10 European SMEs, we found that bottom-up strategy exercises are more interactive. They consider a greater number of views, increase legitimacy, and EDI at the workplace, and yield more process benefits, but are time-consuming and difficult to organise that require special attention to the capability, reciprocity, and credibility dimensions.