This dissertation advances research on evaluation (RoE) through a trio of studies focusing on the role of context and the innovative use of Linguistic Inquiry and Word Count (LIWC) software in formative evaluation in a qualitative research project. The first article extends Coryn et al. (2017) and elucidates how various contextual dimensions--evaluator, stakeholder, organizational/program, and historical/political--impact the quality and outcomes of evaluations. It underscores the intricate relationship between these dimensions and the evaluation process. The second study leverages LIWC to scrutinize the potential interviewer effects on data collection quality, particularly focusing on the authenticity and emotional tone of interview responses. It intriguingly finds that the demographic alignment between interviewer and interviewee does not significantly alter these LIWC summary variables, challenging assumptions about demographic influences on data quality. The third article expands the application of LIWC to identify linguistic patterns that signal the richness of data, aiming to refine data collection methodologies. This article advances formative evaluation techniques by demonstrating how LIWC can uncover nuanced linguistic indicators of data quality. Collectively, this dissertation highlights the critical role of contextual understanding in RoE and establishes LIWC as a formidable tool for improving the ethical and effective evaluation of qualitative research. The dissertation advocates for a nuanced, context-aware, and technologically informed approach to evaluation that promises to elevate the standards and efficacy of formative evaluation of qualitative research. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]