This chapter introduces the TOWS model as a tool to generate alternatives during strategy formulation. Following from SWOT analysis, understanding strength, weakness, opportunity, and threat not only signals the existing condition but also the way forward. In this chapter, SWOT factors are rearranged into four scenarios where firms have strength and opportunity; weakness and opportunity; strength and threat; and weakness and threat. Explanations are embedded in the context of technology-based firms with different internal conditions to cope with opportunity versus threat. The chapter also delves into further challenges of formulating strategies toward digital transformation in different organizational contexts. Lastly, diverse models of strategy formulation are presented as options for leaders of technology ventures.