Objectives Knowledge transfer is recognized as a key determinant of organizational competitiveness. Existing literature on the transfer of knowledge and skills imply diminutive return on investment in training and development due to the low application of learned knowledge to the work environment. Following devolution of health services provision to new counties in Kenya in 2013, Strathmore Business School designed an experiential facility improvement project-based leadership training programme for healthcare managers in the new counties. Selected healthcare management teams participated in the leadership training to improve health systems performance in the devolved counties in Kenya.Despite similar training, the projects implementation contexts were different, leading to different implementation completion rates. The aim of this study was to investigate the reasons for this disparity and then recommend solutions. Design A qualitative study using semi-structured interviews. A thematic framework approach was used in data analysis. Setting and participants Thirty-nine projects team constituting; 33 successful and 6 unsuccessful project teams, were purposively selected based on their project implementation success rates at the end of the leadership training. The managers had undertaken a team-based institutional improvement project. The prioritized projects were housed within; 23 public, 10 faith-based and 6 private health facilities in 19 counties in Kenya. Results Our findings indicate projects completion rates were influenced by (training design, work environment climate, trainee characteristics, team-based coaching and, leveraging on occurring opportunities). Transfer barriers were (inadequate management support, inadequate support, high staff-turn over, misalignment of board’s verses manager’s priorities, lack of technical expertise, endemic strikes, negative politics and, poor communication). Recommendations (needs-driven curriculum, effective allocation and efficient utilization of resources, proper prioritization, effective communication, longitudinal coaching and, work-teams recruitment). Conclusion The findings reveal that unless training interventions are informed by a need-driven curriculum customized to real-world work teams, the potential knowledge and skill transfer can be thwarted.