The future will be replete with Artificial Intelligence (AI) based agents closely collaborating with humans. Although it is challenging to construct such systems for real-world conditions, the Intelligent Tutoring System (ITS) community has proposed several techniques to work closely with students. However, there is a need to extend these systems outside the controlled environment of the classroom. More recently, Human-Aware Planning (HAP) community has developed generalized AI techniques for collaborating with humans and providing personalized support or guidance to the collaborators. In this thesis, the take learning from the ITS community is extend to construct such human-aware systems for real-world domains and evaluate them with real stakeholders. First, the applicability of HAP to ITS is demonstrated, by modeling the behavior in a classroom and a state-of-the-art tutoring system called Dragoon. Then these techniques are extended to provide decision support to a human teammate and evaluate the effectiveness of the framework through ablation studies to support students in constructing their plan of study (\ipos). The results show that these techniques are helpful and can support users in their tasks. In the third section of the thesis, an ITS scenario of asking questions (or problems) in active environments is modeled by constructing questions to elicit a human teammate's model of understanding. The framework is evaluated through a user study, where the results show that the queries can be used for eliciting the human teammate's mental model.