Enabling blended learning scenarios that foster participation and interaction is an important consideration in the design of executive training programs. To investigate this design process, our study focuses on two aspects that are present in such scenarios, namely (1) participant engagement and (2) privacy expectations. This paper presents the pilot deployment of a digital tool within a blended learning scenario implemented by UNCTAD for an executive training program aimed at policymakers and government officials. Our main contribution is a detailed analysis of insights gathered through an observational study with participants from Latin America and the Caribbean. By interpolating data from digital logs, questionnaires, observations, and interviews, our results show that the two aspects investigated play a significant role in fostering interaction among participants. As an outcome of this study, we formulate two hypotheses regarding the design of privacy-preserving blended learning scenarios for validation in future work.