Learning object currently leads the instructional technologist towards more flexible delivery content and online learning. It has triggered discussion about how they should be designed and used. However, most of the learning object related works were mainly focused on the technical-related issues leaving behind the importance of pedagogical factors and issues pertaining to effective learning. In fact, there are further advantages to be gained in the effectiveness of the use of learning object in supporting learning. The paper examines the attributes of learning object in providing a customized and flexible learning environment that is grounded in generative learning environment. The cognitive and pedagogical relationships between generative learning and higher order thinking skills (HOTS) are reviewed. A conceptual model, GLOOTT model, is proposed for the design and development of a pedagogically-enriched Web-based learning system to promote HOTS.