Expertise is vital to any organization’s competitive advantage in the highly competitive landscape. However, as technology continues to evolve and emerge, organizations find themselves in a near-constant state of transformation. Moreover, the rapid pace of technological innovation is outpacing any previous era and contributes to an already complex transforming workplace. As the transformation continues to unfold, the workforce must be equipped to perform in the new operational environment. In other words, the workforce must also transform to keep pace with the workplace. Unfortunately, current methods used to develop expertise are inefficient and consequently require a tremendous amount of time and effort. For example, scholars agree that reaching an expert level of mastery requires more than 10,000 hours and up to ten years to achieve. Therefore, developing expertise within the workforce for the transformed workplace requires Human Resource Development professions to design and implement innovative solutions capable of overcoming these and other challenges created by ever-present transformation. Moreover, innovative and emerging technologies, such as artificial intelligence, are quickly being adopted in the workplace, including in the fields of medicine (Allen, 2018; Harrington & Johnson, 2019) and business (Schneider & Leyer, 2019). These highly complex and emerging technologies provide organizations the power to push beyond the limitations of human performance. Likewise, these technologies provide the potential to outpace the ongoing technological evolution. Human Resource Development professionals must employ innovative strategies that transcend disciplines to harness the power offered by machines as well as circumvent the extremely long lead times to efficiently develop expertise. These innovations must fundamentally disrupt the current methods of expertise development to increase efficiency. Consequently, this begs the question: As humans traverse toward and through the continually transforming workplace, how is the needed expertise developed to equip humans to interact and help organizations establish and maintain their competitive advantage? This question is at the heart of this chapter as the author addresses what is known about developing expertise, innovative and emerging technology, and the possibilities of greater connectedness in the digitally transformed workplace.