HOW? Spend as much time as you can with people relevant to the design topic. Establish their trust in order to visit and/or participate in their natural habitat and witness specific activities.
WHY? This is a good way to achieve a deep firsthand understanding of habits, rituals, natural language, and meanings around relevant activities and artifacts.
(e.g. In exploring opportunities for internet enabled devices, an IDEO team spent time with families from different ethnic, economic, and educational backgrounds to learn about their daily patterns.)