A digitally literate workforce is no longer a choice but an imperative in this current era as organisations seek to develop and enable innovators and shapers of the new digital reality. However, it is not enough to be just digitally literate. Digital dexterity is the new frontier, extending beyond digital literacy by providing individuals with the ability to leverage media, information and technology. In a higher education environment, a digitally dexterous workforce is vital to facilitate innovation in learning and teaching and to keep pace with digital scholarship and research. Developing digital dexterity can be challenging due to varying levels of technological competency and buy-in from staff. The University of Wollongong Library has committed to becoming a digitally dexterous organisation. This paper presents a case study focusing on a small group of staff who developed their digital dexterity organically in a small community of practice. In seeking to reshape and upskill its workforce, an innovative learning model was piloted to encourage both individual and group engagement with applications and technologies. The model centred on personalised, flexible learning and gave staff the scope to learn any digitally focused topic. This case study showcases one example of how staff have employed this model by engaging with the digital humanities. The collective nature of the learning process and freedom to explore enabled the development of digital dexterity through the attainment of, for example, coding literacy and digital curation skills. Both of these, supplemented by improved written and oral communication skills, were acquired to support technology-enhanced learning and research and data curation in a university environment. Through the adoption of a growth mindset the group learnt from setbacks, overcame challenges, embraced self-directed learning, and employed creative thinking. Collective endeavour assisted with the development of technical competencies and adoption of new technologies. The digital dexterity initiative is a work in progress. The key takeaway that is emerging is that providing staff with the freedom to explore and innovate, work together and learn from each other to develop technological capabilities in communities of practice is effective for achieving work and cultural change.