From Rule-Based Decision-Making to Dilemma-Oriented Leadership

Type: Article
Topics: Leadership Development, School Administrator Magazine

September 01, 2026

How an ethical quandary about expectations and trade-offs played out in the work of a school leader
A Black man in suit smiling and talkingBrian Gaston, a senior manager at EdEthics at Stanford University, sought to start a charter school network focused on Black and Latinx communities amid anti-DEI sentiment in Texas. PHOTO COURTESY OF THE SOCIAL INNOVATION AND CHANGE INITIATIVE AT THE HARVARD KENNEDY SCHOOL

In today’s hyperpolarized political climate, superintendents and other education leaders face ethical dilemmas borne of conflicts between their own and others’ deeply held beliefs. These dilemmas may arise around responses to national or global events, curricular choices, parental rights or school closures, among other issues of the day.

To protect themselves, education leaders often rely on preexisting policies or rules to shut down conflict — even sometimes their own internal conflict — and pretend that no other choice is possible. However, risk reduction does not always equate to harm reduction. Many current challenges carry costs due to conflicting values that precedent-based decision-making cannot resolve.

To navigate this complexity, we recommend that education leaders shift from a rule-based leadership approach to a dilemma-oriented leadership approach, which we illustrate through an examination of our lead author’s recent ethical dilemma.

Brian’s Dilemma

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