Evolving social and industry practices, standards and expectations make it clear that the further education and training (FET) sector must help students acquire the knowledge, skills and attitudes that enhance their competency and prepare them for an increasingly complex and digital world. This phenomenological study shares leaders' experiences of managing digital technology change throughout the COVID-19 pandemic that led to the acquisition of the digital skills, qualities and dispositions necessary to support the development of an educator digital mindset for some individuals, but not for all. We also reveal novel insights into how these leaders positioned their organisations for successful strategic change by supporting their educators' engagement in the creative and effective use of digital technology in their chosen discipline, craft or professional area of expertise. We conclude that successful technology change can lead to constructive peer support and resources, create learning spaces that strengthen digital mindsets and professional identity, promote student retention and create successful digital technology-practitioners.