This study aims to analyze how the middle management at university handle with the order versus freedom dilemma--bureaucratic discipline, professional expertise; coordination, communication; managerial planning and individual initiative by giving a university case. A survey was applied on two different sample groups. 607 middle managers and academicians working in six different faculties and two schools in a HEI in 2014-2015 educational year compose the population of the study. Data for the study were gathered with the "Order vs. Freedom Dilemma Scale" and with semi-structured interview form "Opinions on the Order vs. Freedom Dilemma" both developed by the researcher. The findings of the study show that the choice of middle managers on order vs. freedom dilemma is mostly for order. The choice of sub-dimensions related to order and/or freedom is important and each of those sub-dimensions need continuous development. Furthermore, it is suggested that individual orientations, professional norms, ideals and professional discipline all together with the institutional structure can be improved correspondingly and become more effective in practice. Besides, supporting the staff to reach each other in a better and closer communication space is also suggested by starting an interactive, effective and sustainable communication mechanism on middle and lower levels.