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A quick search of the headlines of major newspapers reveals a treasure trove of technology procurement gone wrong. While the private sector seems to adopt and implement new technology seamlessly and quickly to deliver for customers, the government struggles to accomplish technology purchases and integrations with the same ease. As governments in the United States are looking to retain their current workforce and attract the next generation of workers, the technological capabilities and ethos of governments will be paramount. With nearly every industry being transformed by technology and Generation T being the first generation to have an ingrained “technology first” mindset, the ability of governments to attract these workers depends, in large part, on the ability to transform their government technology culture, policies, and practices.

In this chapter, the authors examine the administrative branch and observe two key components at the root of most technology failures: poor organizational structure in the bureaucracy and the lack of an empowered Chief Information/Technology Officer. Building upon case studies from Massachusetts and California, this chapter looks at the factors related to failure or success to understand the technology procurement culture. The chapter concludes by presenting four key “best practice” principles of public policy and administration that can be implemented by almost any governmental entity to improve their acquisition and implementation of technology.