Two of the biggest issues facing large organizations today are knowledge transfer from the retiring Baby Boomers to their younger replacements, the Gamers, and the retention of those younger employees. Retirees are replaced by people 34 years old or younger who think, learn, believe, respond, and work differently further increasing the cultural gap that must be traversed in order to successfully transfer knowledge. This younger demographic is raised on technology and may not remember a time when there were no computers, video games, mobile devices, and the Internet. Large organizations aspiring to stay relevant must learn to take advantage of these unique traits. For organization that utilize repetitive work processes involving ruggedized handheld computing tools, both of these issues mentioned can be remediated through the adoption of modern technology. Some ruggedized handheld device manufacturers, however, have been hesitant to embrace consumer-implemented solutions such as the removal of all physical keys in order to incorporate touchscreen only input. Using Baby Boomer and Gamer-aged workers from a large transportation company experienced with ruggedized handheld devices, a time and error evaluation was performed to determine which input type is best by generation. This study found that moving from physical keyed devices to ruggedized handhelds with touchscreens only is a productive move for an industrial workforce but it’s the Boomers who stand to benefit from this change the most, not the Gamers. This study also identified near future requirements for the next iteration of ruggedized handheld devices based on the expectations of members of the current and future workforce. Results showed that participants from all generations selected a device that followed the touchscreen only model for data input. Experienced users from all generations preferred a smaller device with a large screen size. Lastly, Lean and Six Sigma were combined and their benefits explored in an effort of implementing manufacturing quality tools into a global, service-based, logistics organization. These tools and principles were used to improve the quality and timeliness of selecting and implementing a new ruggedized handheld device for the line-level workers on a global scale.