In 2018, the University of Wollongong (UOW) launched The Future-Ready Library strategy. The inevitable question arose: How does one become ‘future-ready’? The answer lies, in part, in proactively engaging with evolving technologies and improving individual staff digital dexterities. Coinciding with release of The Future-Ready Library strategy, the Digital Literacy Workplace Program was put in place to foster upskilling opportunities for Library staff. One of the outcomes of this program was the creation of a local Digital Humanities Community of Practice in 2018. This article focuses on the transformative journey of the Community of Practice in developing staff digital dexterity through the completion of mini projects. These mini projects incorporated both hard and soft skillsets to develop agile, future-focused, T-shaped professionals. While initially directed at developing digital dexterity and increased knowledge of the Digital Humanities, the Community of Practice recognized the need for adoption of a broader, more strategic approach, to support clients and staff in this area. This resulted in the launch of the Digital Scholarship Strategy project in 2020. The project group was tasked with scoping the feasibility of initiating a Library-led roll-out across the organization, or a tighter focused implementation within the UOW Library operational environment. The expedited move to online teaching and learning as a result of the COVID-19 pandemic highlighted the timeliness and applicability of these initiatives.