This mixed-methods comparative case study examined the differential effectiveness of time-based versus output-based workplace management systems on employee and organizational outcomes across Spain and Uganda, representing developed and developing economy contexts respectively. Conducted between January and August 2024, the study employed stratified random sampling to survey 450 employees (225 per country) across manufacturing, service, and technology sectors, supplemented by 30 semi-structured interviews with organizational leaders. Quantitative analysis proceeded through univariate descriptive statistics, bivariate correlations and t-tests, and structural equation modeling to test hypothesized relationships and mediating effects of technological readiness, cultural power distance, and labor law flexibility. Results demonstrated that output-based management systems were associated with significantly higher employee performance (r=.312, p