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In September 2021, Simone Badioli, the CEO of AEFFE SpA, met with an external consultant, Giulia, and a few company directors to lay out a plan for the upcoming future. After two years of forced telework due to the COVID-19 pandemic, AEFFE had to make important decisions: whether to stably provide its employees with a Smart Working (SW) policy or not, and whether an eventual policy should be homogeneously applied to all the various organizational areas or be tuned to their different needs. The case requires students to evaluate the business or change case for SW in general and at AEFFE in particular. It also asks students to draw a possible policy for AEFFE that regulates the access and use of SW. The case allows for a critical evaluation of SW applicability across different settings and functional areas. It leads students to reflect upon the potential costs and benefits of flexibility while wrestling with questions about business strategy, inclusion, cultural change and heritage, organizational aspects of creativity, and companies' responsibilities to various stakeholders. Students also engage in critical appraisals regarding what 'smart' working means in any given context and explore the challenges of implementing new ways of working in companies where the cultural premises of prior success are deeply embedded in the organizational walls.