Though long recognized as a leading proponent of Critical Social Theory, Jürgen Habermas has achieved limited influence in educational administration and research. I argue that this circumstance is in large part due to a gap in understanding the historical changes evident in Habermas's theorizing of 'practical discourse' as a key component of his Discourse Ethics. Once the transcendental-pragmatic reconstruction of practical discourse is better understood, this dialogic ideal and its necessary conditions can be applied to guide, assess and critique educational policymaking from a critical perspective. As additional support for applications of practical discourse to educational policymaking, I further outline and develop the value of 'rational trust' as an important means of bridging between the counterfactual nature of its ideal conditions and the real-world contingencies encountered by administrators.