The design and implementation of questioning, specifically in regards towards a higher level of thinking, is a common practice in many secondary social science classrooms (Bickmore & Parker, 2012). Questioning can help the teacher develop critical thinking concepts, scaffold discussions, and prod students towards an elevated level of cognition (Yang, Newby & Bill, 2005). It can also aid in guiding group discourse and help students in developing a rational understanding of a problem or concept (Byun, Lee, & Cerreto, 2014; Godfrey & Grayman, 2014). Yet many educators may feel limited or not prepared in their conception and ability towards this practice. The confusion is merited, in some respects, as questioning is a skill not easily mastered or understood. This article explores and defines "question: as an interrogorative, an abstract, a rhetorical inquiry, a point of part of a controversy and debate. Regarding structure, a question can be defined as both well-fitted, with clear and expected outcomes, or as ill-fitted, or lacking expected outcomes. The ill-fitted type of structure, usually described as an open ended question, is generally seen as more productive towards achieving higher order thinking (Byun, Lee, & Cerreto, 2014). Towards a group or class, such teacher led questioning can help in developing critical thinking dialogues where respondents engage in civil discourse on a variety of topics, some possibly controversial in nature. This dialogue can be beneficial to students in many ways. To engage in dialogue of opposing views needs to involve a multimodal perspective utilizing both active and passive learning styles. If the process is respectful and engaged, students can develop new and different information as compared to their own perspective or lens. Such are necessary learning activities for the critical analysis of topics relevant to today as well as the skills needed in discussing these issues in a civil, behaved manner. The author maintains that teacher concerns about disruption and blow back are very real and can carry negative repercussions, however critical thinking and student dialogues are such powerful tools for young adults and children that educators still need to try. America is changing, and educators need to help students in understanding that even if the older generation my be uncomfortable in doing so.