Since ages, theorists have been hypothesising that skill in speaking can be measured positively corelated with the Contextual Intellectual (CI). As Aristotle said, Man is a civic animal (1), and he uses intelligence based on the context or event or any other situation, not on the Intellectual Quotient (IQ) levels. Contextual Intelligence (CI) is, although, considered the tacit ability or knowledge and can be measured over language abilities and skills. This research article targets to assess speaking skills by using CI at undergraduate level. 30 undergraduate heterogenous students have been tested if they could use or develop CI to speak freely and clearly in L2 classrooms and labs. To assess Speaking skills, CEFR speaking Skills rubrics have been adopted. Speaking Skills and Contextual Intelligence (CI) have been identified and notified separately after taking outputs of the stipulated aspects from experimental group. Analysing and assessing speaking skills by CI have been embedded with the CEFR rubrics. Stern Berg’s Triarchic Model (3) (Creativity 1999) and Lang’s Cognitive Psychology Models (12) (1971) have been formulated to test the reliability of the empirical date to assess the tacit knowledge of the heterogenous group. Investigational Words/phrases: Assess, Contextual Intelligence, Empirical Data, Speaking Skills, Tacit ability