Interventions tailored to individual smoker characteristics have increasingly received attention in the tobacco control literature. The majority of tailored interventions are generated by computers and administered with printed materials or web-based programs. The purpose of this study was to examine the tailoring activities of community lay health influencers who were trained to perform face-to-face brief tobacco cessation interventions. Eighty participants of a large-scale, randomized controlled trial completed a 6-week qualitative follow-up interview. A majority of participants (86%) reported that they made adjustments in their intervention behaviors based on individual smoker characteristics, their relationship with the smoker, and/or setting. Situational contexts (i.e., location and timing) primarily played a role after targeted smokers were selected. The findings suggest that lay health influencers benefit from a training curriculum that emphasizes a motivational, person-centered approach to brief cessation interventions. Recommendations for future tobacco cessation intervention trainings are presented.