The following article is a guest opinion piece submitted to AWSP.
There is probably a conversation you didn’t have last year. A teacher whose classroom management never stabilized. A staff member whose personal circumstances made a hard year harder. A team dynamic that never got addressed before summer broke the momentum.
You told yourself it would resolve on its own, or that the timing wasn’t right, or that the person was going through enough already. Summer came and the pressure to deal with it went away with it.
Now the school year is starting again, and the same person is walking back into the same role. If the conversation didn’t happen, the problem didn’t go anywhere. It is waiting exactly where you left it, and this year will produce the same result unless something changes before the pattern repeats.
The instinct, especially in schools, is to give people room. Educators understand hardship. That is often what makes them good at this work. But there is a version of that understanding that becomes its own problem: where understanding someone’s difficulty becomes the reason nothing is ever directly addressed.
That version is not a leadership strength. It is avoidance with a more acceptable name.
Here is what this costs a school. When direct feedback is consistently deferred because of sensitivity to a teacher’s or staff member’s circumstances, the rest of the faculty is watching. They learn that circumstances can explain away performance. That difficult conversations do not actually happen. That stated expectations are not the real expectations.
The most immediate cost is usually to the person being protected. A teacher continues with a classroom management pattern that is not working, without the honest feedback that would let them change it. The kindness meant to protect them is actually depriving them of information they need, and by the time the situation can no longer be deferred, it often involves a parent complaint or a student who lost a year, rather than an early conversation that could have changed the outcome.
The distinction worth making is between empathy as understanding and empathy as permission.
Empathy as understanding says: I see this has been hard for you. That understanding changes how the conversation happens, the tone, the timing, the support offered alongside the honesty.
Empathy as permission says: because this is hard for you, I will wait until it is less hard. This is not empathy. It is the use of empathy as a shield against the leader’s own discomfort, not the teacher’s.
The most empathetic thing a school leader can do is give someone honest feedback early enough for it to matter, delivered with care and specificity and genuine investment in their ability to respond to it.
Schools that lead with empathy as their dominant style often develop a culture of exceptions. Every difficult situation has a reason. Every performance gap has an explanation. The team experiences this not as a kind culture but as an unclear one, and the teachers who hold themselves to genuine standards begin to feel their investment is not being matched by those around them.
The fix is to hold the empathy and the directness simultaneously rather than letting one cancel the other. You can say: I understand this has been a difficult period for you, and I want to support you through it. I also need to be direct with you about what I am seeing and what needs to change. Both can be true in the same conversation.
Heading into this school year, it is worth naming: is there a conversation you have been giving space to that actually needs to happen directly? What is the delay costing the person who needs to hear it?
Hary Askotzky is CEO of The PRISM Group and author of The Creator Blueprint. He brings nearly two decades of senior school administration experience to his work as an organizational architect, consulting with schools and businesses on structure, clarity, and leadership.
