How to manipulate free speech guarantees.
The Trump Administration needed to deal with the problem that the colleges with the worst speech codes are conservative religious colleges. The solution was to include a hypocritical rule in the Executive Order that says private colleges will be judged only by “compliance with stated institutional policies.” Since conservative colleges openly state that they suppress free speech, they will be immune from any action (not that any Trump official would ever dare to punish a conservative college).
By contrast, if a more liberal private college aspires to protect free speech, they can have their federal funds taken away based on a Republican bureaucrat’s regulatory interpretation of the campus’ values. This Executive Order will tend to reduce free speech at private colleges, because colleges will have an incentive to remove any promises to protect free speech in order to avoid being vulnerable to federal funding cutbacks. And if private colleges have policies that provide stronger protections for free speech than the First Amendment (as many do), they can lose federal funding even if they meet First Amendment standards.