Witness intermediaries facilitate communication between legal actors and children or other vulnerable populations, and sometimes intermediaries assist in investigative interviews. This research explored the skills of investigative interviewers and intermediaries (who either had experience acting in that role or were eligible to do so) in identifying problematic questions during interviews. Forty-one participants (18 interviewers, 23 eligible or experienced intermediaries) listened to excerpts from interviews with three alleged victims of sexual or physical abuse which contained a mix of appropriate and inappropriate questions. Participants paused the audio whenever they wished to make a comment and also completed a knowledge test on questioning best practices. Interviewers identified more problematic questions and scored higher on the knowledge test than intermediaries. Whereas interviewers were primarily concerned with the extent to which the interview involved open-ended questioning, intermediaries focused on the extent to which questioning involved supports and clear scaffolding. The findings suggest that well-trained interviewers are equipped to handle most questioning issues with children independently; however, intermediaries’ attentiveness to question scaffolding suggests they might aid communication with interviewees facing more pronounced communication challenges (e.g., developmental delay).