Complexity manifests in no clearer arena than women's political leadership and overall empowerment. The nature of the leadership journey, comprised of multiple events and milestones, paired with environmental factors like COVID-19, adds to this complexity. This chapter tackles the challenges of measuring program impact in advancing women's leadership by discussing the Vital Voices Global Partnership (VVGP) approach. Using an adapted contribution mapping and analysis tool, VVGP identified contributions at three levels: programmatic, individual, and community. The tool allowed VVGP to collect evidence about VVGP's contributions to improved political leadership and the overall VVGP model's theory of change (TOC).One of democracy, human rights, and governance (DRG) programming's many complex objectives is the goal of women's empowerment, including supporting women in leadership positions so that their voices are included in efforts to advance human rights and equal access to elected offices. Measuring the impact of this goal is challenging because of its complexity, which arises because the leadership voyage is not linear and continuously evolves, with the leader taking multiple pathways and reaching outcomes as her vision is executed. Furthermore, in the trajectory of leadership and success, power over, within, and for are essential to change. Moreover, learning from previous work is limited due to the added challenge of holistically evaluating program interventions' contributions and attributions to changes in women's political leadership. This chapter tackles improving the measurement of complex programs to advance women's political leadership by discussing