Given recent demographic changes, adapting the office environments of older knowledge workers to their needs has become increasingly important in supporting an extension of working life. In this paper, we present a case study research of older knowledge workers in Romania, with the goal of gaining bottom-up insights that support the ideation, design, and development of features for a smart work environment. Utilizing a multi-method approach, we combine (1) contextual interviews and observations, (2) an analysis of needs and frictions for deriving insights, (3) an ideation workshop for eliciting potential features, (4) an online survey among experts for evaluating the final feature ideas, and (5) early stage prototyping of selected feature ideas. Following this comprehensive yet efficient approach, we were able to gain a rich understanding of the work realities and contexts of older knowledge workers and to transform that understanding into a concrete set of prioritized feature ideas.