Swedish police are implementing a new model for investigative interviewing. Previous research has highlighted that investigative interviewing is difficult to operationalize and teach to recruits. This study aimed to understand what Swedish police teachers value as important interpersonal skills for investigative interviewing as well as what strategies and struggles these teachers face when teaching recruits. Interviews were conducted with six experienced interviewing teachers at Swedish police training programs. Data were analyzed using thematic analysis. The teachers described that taking the interviewee’s perspective and accepting responsibility to build rapport, as well as social and situational flexibility were important skills for interviewers to process. When describing their strategies and struggles in teaching, the teachers described the need to bridge theory and practice, train flexibility through diverse scenarios, adjust to students’ social maturity and ability to self-reflect, and work with limited resources. This study also highlights how interviewing teachers express a need for adequate time and resources to be able to help recruits develop the necessary skills for interviewing.