In this study, we qualitatively evaluate how participants engaged with role-taking aimed at increasing resistance to persuasion in the context of social engineering (SE). We report on interviews conducted with a subset of participants from a larger experimental study, in which individuals were assigned to one of several roles: persuader, persuadee, or learner of literacy materials. The literacy group was included in the interviews to support benchmarking. A total of 17 participants were interviewed to explore and identify the factors that resulted in changes in their behaviour related to resistance to persuasion, whether positively or negatively. Our research indicates that enhancing resistance to persuasion goes beyond knowledge transmission; it requires thoughtful design that fosters motivation, triggers dissonance for change, and ensures personal relevance. Overconfidence could hinder progress, highlighting the need for role-taking behaviour change interventions that challenge rather than reinforce self-perceptions. The integration of these elements can support developing more effective strategies that cause real behaviour change in resilience against the manipulative use of persuasive tactics in SE.