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Set in 2022, this case describes the digital transformation strategy of Davivienda— a leading player in Colombia’s commercial banking and one of the companies belonging to Grupo Bolívar, a major Colombian financial conglomerate—and the bank’s upskilling and reskilling programs adopted to support that process. Through its upskilling programs, the bank provided training courses and development opportunities for employees needing updated or more advanced skillsets to continue performing their roles. By deploying reskilling programs, Davivienda sought to offer learning opportunities to employees so they could acquire new skills and move on to new roles at the bank. Yet, as new industry trends called for more agile approaches, these programs would often take more time than what the bank could afford to wait. Dealing with this concern, Miguel Cortés, Executive Chairman and CEO of Grupo Bolívar, and Javier Suarez, Davivienda’s CEO, would soon meet with Davivienda’s leadership to assess the long-term benefits of Davivienda’s upskilling and reskilling programs. How could Davivienda find a balance between strategy and culture under the existing conditions? Should the bank prioritize decisions that align more with its strategic commercial goals, even if it meant deviating from some cultural principles?