This workshop addresses the need for effective evaluation of trainings in digital competence, a critical challenge across Europe. While current evaluation methods are limited, the Digital Competency Training Assessment Model (DTCAM) offers an expanded framework incorporating behavioral changes, organizational conditions, and sustainability criteria. Central to this approach is the Digital Training Companion (DTC), a web application utilizing data science for ongoing, structured monitoring and assessment. The DTC supports formative assessment, data-driven feedback, and self-regulation for trainers, multiplicators, and students. This workshop explores the theoretical underpinnings of DTCAM, provides hands-on experience with the DTC, and examines its application in real-world settings. Results from an exploratory field study will be presented, demonstrating the DTC's potential to improve digital teaching competence transfer and motivation. The workshop aims to equip participants with the knowledge and skills to implement the DTC in their own contexts, ultimately fostering sustainable improvements in teaching and learning, and contributing to the European agenda for digital competence in education.