Designing approaches to support knowledge intensive work has been documented to be critical and costly. Research has shown that knowledge workers frequently evaluate KM efforts as missing the mark. They are too often left without the help they need for constructing knowledge-based solutions. Knowledge workers point to failures not so much in retrieving topically-perfect-information but rather to communication gaps, such as systems that do not address work demands and informing needs in complex, changing, and sometimes elusive situations. This research used an interviewing approach informed by Dervin's Sense-Making Methodology. The aim was to allow digging deeply to understand hidden depths of informing practices that rarely have come to light in user studies. The ultimate aim is to design systems that support knowledge creation anchored to knowledge worker informing practices and to the situationality of these practices. The purpose of this paper is to present an exemplar study focusing on the challenges of doing user research in such a way that it usefully informs the design of knowledge management systems intended for use in knowledge-intensive work in the for-profit context. Sense-Making Methodology is presented as an alternative and more powerful approach to studying knowledge creation work.