Investigative interviewing in any context is a complex area that requires specialist knowledge and skills. In the context of regulatory enforcement, corporate or workplace investigations, the complexities can be even greater. One reason for this is what is described as the ‘blurring of legal forms’ (Ashworth, Law Q Rev, 116:225–256, 2000) or the functional distinctions that exist between criminal and civil law and between regulatory breaches and ordinary wrongdoing (McGrath, Corporate and white collar crime in Ireland: a new architecture of regulatory enforcement. Manchester University Press, Manchester, 2015). Another reason why interviews in this context will be challenging is the specialist and technical knowledge often required to understand the offending. Despite the proliferation of entrants to the investigative arena there is little consistency in terms of standard or level of training and guidance for interviewers. It has been argued that ‘Regulatory criminal law is all but ignored by most criminal law texts and journals’ (Chalmers et al., Post-corroboration safeguards review report of the academic expert group. Project report. The Scottish Government, Edinburgh, 2014). This tends to ignore the emerging modes of governance for dealing with criminal wrongdoing including regulatory criminal and civil strategies (Brown and Scott, Regulation in Ireland: history, structure, style and reform, 2010). This chapter aims to address this gap by outlining the complexities and challenges involved in interviewing in the context of regulatory corporate and workplace investigations. It will provide guidance to conducting interviews in this context and discuss how concepts such as the fraud triangle and related models can be used to support interviews in this context.