During the Re-imagine 2018 conference held at Birmingham City University, one of the several discussion streams was tasked with identifying issues faced by current middle leaders in further education. The purpose of the ongoing discussions was to then re-imagine a future where middle leaders could meet these challenges, develop plans the further education sector they imagined and provide a space to make suggestions for action. This paper distils these extensive conversations and casts a spotlight over several areas of significance. The paper offers an idealised approach towards a utopian goal for middle leaders in Further education while drawing attention to real and current problems. Beyond its utopian goals, the paper further draws attention to pertinent current issues that given appropriate support and autonomy, middle leaders may wish to explore and seek to engage in ongoing discussions for the benefit of learners in the sector.