Objective Mentorship programmes have been shown to boost camaraderie, enlightenment and positive motivation, as well as, generate a mentoring culture in the workplace. There is limited literature focusing on medical mentorship programmes in Trinidad and Tobago. The research team plans to implement and evaluate a year-long mentorship programme within the Eastern Regional Health Authority on the island. Prior to this undertaking, a pilot study was conducted at the Sangre Grande Hospital to identify potential obstacles. Methods The pilot was conducted between September 1st and November 30th, 2020 with participants being recruited from three departments at the Sangre Grande Hospital. Mentors were pre-selected and mentees matched based on responses from a pre-pilot study questionnaire. Participants were required to complete a questionnaire once per month during the three-month pilot to evaluate programme effectiveness. Descriptive statistics were used to analyze data. Results Participants included five mentors and seven mentees. This resulted in an overall participation rate of 15%. Post-mentorship questionnaire indicated that time commitment was a major challenge in participation. Even though each participant was required to complete a monthly feedback questionnaire at the end of each month, there was only a 38% mentee and 33% mentor feedback response rate. Conclusion Implementation of a mentorship programme may face many challenges including obtaining participants and feedback during the programme. For the planned continuation and expansion of this mentorship programme, modifications would be made to increase participation rates and encourage feedback.