Reskilling has become a critical corporate competency for survival and advancement in the modern era. Yet it’s a competency few organizations have built, much less mastered. While efforts have been made toward reskilling with some notable successes, the reality is, people and organizations are struggling to keep pace and often fail to plan for reskilling at all. This new reality demands the enterprise create a malleable infrastructure and growth mindset that enables always-on transformation and supports ongoing reskilling. It also calls for organizations to create cultures that foster a thirst for constant learning among employees. In this white paper, we offer suggestions for how leaders can pause to rethink and adjust outmoded, shorter-sighted efforts and attitudes about reskilling, and prepare themselves and their workforce for an undefined future.