Capitalizing on the power of qualitative approach in drawing out the multiple layers of meaning entrenched in subjective realities, this phenomenological inquiry described the lived experiences of 12 Filipino medical technology deans, as they face their struggles in managing their organization. An in-depth, semi-structured one-on-one interview which lasted for 1-2 h was conducted. Field texts were transcribed and analyzed using a repertory grid and through constant comparative analyses, an interesting model and a set of conceptual themes about deanship struggles were emerged. The 3-D model of deanship struggles, which is a product of the sharing of the respondents, provides a panorama of how Filipino medical technology deans balance (i) superiority and relationality; (ii) rule and role; (iii) obligation and allocation; (iv) personal and professional life; and (v) scholarship and leadership in an educational milieu of (i) prudence; (ii) transparency; (iii) justice; (iv) productivity; and (v) excellence using the gifts of (i) understanding; (ii) flexibility; (iii) bargaining; (iv) hard work; and (v) risk taking. Findings in this paper provide a valuable lens through which the Filipino medical technology deans' mindset as organizational managers could be viewed and understood