Critical listening is comparing what is heard to some standard or cognitive evidence. The creative listener analyses the statements and facts throughout this process to generate critical judgments. This highly intentional endeavor requires a questioning and analytical mentality to conclude or act on the judgments formed through creative listening. The capacity to make knowledgeable judgments while hearing analytically to discern both qualities and faults is the goal of critical listening. The main goal is pedagogical and concerns designing and testing a tool that could measure students’ critical listening skill improvement during a speech course program. A total number of N = 170 learners participated in qualitative-experimental studies in which we developed a t-test and program to develop and assess critical listening skills. Results show that students’ listening skills improved in specific aspects of critical listening at both times. Effects were more significant in the second round due to adjustments to the program curriculum and the assessment tool. Results support the impact of the intervention by modest to high effect sizes and the construct validity of the assessment tool. We consider the improvement found in the current study a vital beginning and recommend that listening skills become an integral part of the curriculum at the undergraduate level. It would be essential to do a follow-up measurement to verify if the learners retain the critical listening skills beyond the current course and use their spontaneously inappropriate real-life situations.