This book represents a three year long qualitative phenomenological study seeking to understand the attitudes and beliefs drawn from small to medium enterprises (SME) executives’ lived experiences about information technology adoption practices. A sample of 21 small and medium-sized executives and managers in the Chicago area participated in the qualitative, phenomenological study. The data and analysis highlighted critical themes in the success and failure regarding technology adoption practices in SMEs. The core themes interrelate to form the basis for identifying a solid foundation for SME executives and managers to embrace successful technology adoption and investment practices through strategic planning, consistent IT practices, and company leadership.