At University of Wollongong (UOW) Library we have a long standing and authentic commitment to supporting professional development. A regular series of professional development, learning and sharing sessions are an established part of our staff culture and part of our organizational DNA. Our development activities have often been a vehicle for facilitating organic learning as evidenced by the Digital Dexterity Program for Library Staff. This paper discusses the history and benefits of this program, and its continued evolution toward developing future ready Library staff