This document discusses executing digital strategy in a multi-generational workplace. It notes there are different generations currently in the workforce with different preferences for communication and technology adoption. Younger generations are more comfortable with new technologies and prefer instant communication, while older generations prefer more formal communication and are less comfortable with new technologies. The document recommends having executive leadership, a steering council, technology champions, and all-staff engagement to help drive cultural change and adoption of new digital strategies. These groups can help socialize new technologies, train other employees, and promote a culture of innovation. However, legacy systems and cultural differences between generations also introduce challenges to digital transformations.