Introduction: As young healthcare professionals (HCPs) enter the workforce, they find challenges adapting as academic training and workplace settings often do not mirror each other. Mentorship is a possible solution to help bridge this transition. The aim of this study was to gather information from HCPs with regards to their views towards mentorship as a strategy to help in the transition of newly qualified HCPs from study to work. Methods: Two 3-hour interactive workshops entitled “Bridging the Study-Work Chasm” were organised, and participants were invited to complete a survey voluntarily after the workshop. The survey comprised questions regarding the benefits of mentorship, qualification of mentors, time commitment for mentoring, elements of an effective mentorship programme, and barriers to its effectiveness. The anonymised responses were analysed descriptively. Results: Fifty-two out of 62 participants from various healthcare backgrounds completed the survey. 96.2% of respondents felt a study-work chasm exists in the healthcare workplace with 90.4% indicating that a mentorship programme would help to bridge the chasm. More than 70% of participants agreed or strongly agreed that mentoring would boost confidence, reduce anxiety, and aid in study-work transition. It was identified that to produce a more effective mentorship programme, time commitment, training, and proper organisation of the programme would be necessary. Conclusion: It was perceived that a mentorship programme can help to bridge the study-work chasm in the healthcare landscape in Singapore, and will best serve mentors and mentees by committing the proper time and training to ensure its effectiveness.