According to IBM’s Institute for Business Value report, 5 Trends for 2022 and Beyond, digital transformation is a top priority for many organizations. Yet, many firms fall short of building robust digital talent pipelines that are needed to support digital strategies and transformations. This paper offers a three-pronged strategy for helping firms develop digital expertise. The three components include: 1) hiring expertise that is needed immediately, 2) engaging on-demand leaders, and 3) developing digital expertise and culture for the long term. Page 3 offers 14 questions firms can use to a) determine what digital expertise is needed and b) how required digital experience will vary depending on the organizational role. For example, when determining digital talent needs, firms can ask questions such as: How do digital opportunities and threats drive our overall strategy? Compared with our peers, how digitally enabled are we today? Which emerging technologies are most likely to disrupt our business model, and do we have the knowledge to adapt to those disruptions? Regarding roles, firms can ask: In which roles are digital capabilities critical to implementing all or part of our strategy? Which leadership roles do we need to ensure are filled for the long term by people with strong digital capabilities? Other ideas are discussed that can help organizations develop and refine their digital talent strategy.