Group work is a common strategy of collaborative learning, practiced both inside and outside classroom. Irrespective of the subject matter, learners, either being assigned by the teachers or being self-employed, tend to carry out group work. It is evident that often learner experience various difficulties when they are involved in group work outside rather inside the class. Pertinently, this study aimed at identifying the difficulties undergraduate students face outside the class and presenting some effective ways of overcoming them. The study undertook Tuckman (1965), Connery (1998), Beebe and Masterson (2003) and Barkley et al. (2014) to elicit theoretical ground. Mixed-method research strategy was applied. Findings of the study suggested that learners witness problems in forming, storming, and performing stages. Individualism also impeded their group work. Participants of the study called for teachers' monitor to diminish problems.