In this chapter, the comparison of the NATO and the ILO reveals similar administrative styles despite them having almost nothing in common in structural terms. While NATO’s servant style is not particularly astounding, given its policy area, mandate, and functional design, the ILO’s case is puzzling. Despite it being an organization with rather broad autonomy, (normative) authority, and high legitimacy, the ILO’s IPA regularly behaves very passively when it comes to putting its own stance on the IO’s outputs. We show that their similar servant styles can traced back high internal challenges and to the perception of not particularly pronounced external pressures. In conjunction, the constraints arising from the former and the sense of security stemming from the latter render more entrepreneurial behaviour neither possible nor necessary.