Interviews with stakeholders can be a useful method for identifying user needs and establishing requirements. However, interviews are also problematic. They are time consuming and may result in insufficient, irrelevant or invalid data. Our goal is to re-examine the methodology of interview design, to determine how various contextual factors affect the success of interviews in requirements engineering. We present a case study of a Web conferencing system used by a support group for spousal caregivers of people with dementia. Two sets of interviews were conducted to identify requirements for a new version of the system. Both sets of interviews had the same information elicitation goals, but each used different interview tactics. A comparison of the participants? responses to each format offers insights into the relationship between the interview context and the relative success of each interview technique for eliciting the desired information. As a result of what we learned, we propose a framework to help analysts design interviews and chose tactics based on the context of the elicitation process. We call this the contextual risk analysis framework.