Introduction: Performing a clinical procedure requires the integration of technical clinical skills with effective communication skills. We report our study to explore the feasibility of a technique to teach and assess the skill of urethral catheterization. Experimental: A qualitative structured observation and interview based assessment of the participants for the said skill. 70 Residents, postgraduates and duty doctors performed the skill of urethral catheterization in real clinical situation.Procedures were observed, video recorded and assessed by tutors from an observation corner. Participants received immediate feedback from the tutors and patients as well. Group interviews explored the response of the participants, patients and the tutors. Results: The situation provided a real clinical situation. It was feasible to teach and assess in terms of time, facility and resources within the institution. Participants found the opportunity to integrate communication and technical skills valuable, challenging and an appropriate learning experience. Immediate feedback was especially highly valued. Conclusions: This study describes and demonstrates the feasibility of teaching and assessing skill of urethral catheterization.