Pilot training and recruitment is of fundamental importance for the aviation industry. Yet, a number of Commercial Pilot’s License (CPL) applicants trained by Approved Training Organizations (ATOs) fail their airline assessments. To provide some clarity on why this is happening, we conducted in-depth interviews with twelve industry professionals and a detailed documentary analysis was undertaken. We found that the main reasons are: (1) Lack of preparation or technical knowledge; (2) Poor communication skills; and (3) Poor display of teamwork and leadership. The paper suggests that regulation should be implemented for ATO’s to use screening processes on potential students to increase quality or Airline Pilot Standard Multi Crew-Cooperation (APS MCC) system, as an additional training system on top of what is being taught in ATOs. Regulations should further be linked with regular audits in place for smaller airlines to increase the effectiveness of their pilot assessments and recruitment processes in order to increase safety. Areas of further research as also identified.