AI can help us communicate more effectively, yet it can also make communication feel less authentic--school leaders must navigate carefully.

“My boss probably used AI”: What school leaders need to know about AI, authenticity, and trust


AI can help us communicate more effectively, yet it can also make communication feel less authentic--school leaders must navigate carefully

Key points:

A friend recently told me he had received a promotion. He was delighted, of course, and mentioned that his boss wrote some very positive comments about him in an email.

Then he added, almost as an afterthought, “I think he used AI.”

He laughed and shrugged. “Well, it doesn’t matter. I got the promotion.”

I laughed too, but his comment made me think.

Why did the possibility that AI had helped write those words seem to reduce their value? His boss still observed his work, made the decision to promote him, and recognized qualities that deserved praise. If AI simply helped him articulate those thoughts more clearly, had the message somehow become less authentic?

This is a question school leaders increasingly need to consider.

The efficiency dilemma in leadership

AI is increasingly part of everyday leadership work, from drafting emails and reports to organizing ideas. Used thoughtfully, it can reduce administrative burden.

But when AI enters more personal communication—feedback, recognition, recommendations, and appraisals—the question is no longer simply:

Did you use AI?

A more important question is:

What did you ask AI to do?

AI-assisted expression vs. AI-substituted judgment

There is a significant difference between AI-assisted expression and AI-substituted judgment.

Imagine a school leader who knows why a teacher deserves recognition. She has observed their practice, relationships with students, support for colleagues, and professional growth. She knows what she wants to say but uses AI to express it more clearly.

The words may be AI-assisted. The judgment is still human.

Now imagine a leader asking AI to generate an appraisal of an employee they barely know, accepting praise or targets they have not independently formed or verified.

Here, AI is no longer simply helping with the writing; it is beginning to substitute for professional judgment.

A document written entirely by a human is not necessarily thoughtful. A document refined with AI assistance is not necessarily thoughtless.

Authenticity may have more to do with where the thinking occurred than with who typed the words.

The paradox of polished language

AI can help us communicate more effectively, yet it can also make communication feel less authentic. A beautifully written message from a head teacher may now leave a teacher wondering: Did they write this, or did they just put my name into ChatGPT?

That matters because recognition carries weight when people feel genuinely noticed.

Consider this:

Thank you for your tireless dedication and unwavering commitment to our students.

There is nothing wrong with the sentence, but it could describe almost anyone. Compare it with a message referring to how a teacher reassured a nervous parent, adapted a lesson for a struggling student, or supported a colleague.

One contains polished praise. The other contains evidence that someone noticed.

Specificity builds trust; polish alone does not.

Redefining authenticity

Authenticity cannot simply mean typing every character ourselves. Leaders have always received help communicating; AI changes the scale and sophistication of that assistance.

What matters is whether the leader retains ownership of the message.

There is a considerable difference between asking AI:

Can you help me express this more clearly?

and asking:

Tell me what I think about this person.

One supports human thinking.
 The other risks replacing it.

Three questions before you press generate

Before using AI to draft an appraisal, recommendation, recognition email, or other personal communication, three questions may help.

1. Could I explain the evidence behind these words without looking at the screen?
If I describe a teacher as innovative, collaborative, or highly effective, what have I actually observed? AI can help with the vocabulary, but the evidence should come from the leader.

2. Am I asking AI to express my thinking, or to do the thinking I have avoided?
Struggling to phrase a judgment is different from struggling to form one. AI may help with the first; the second requires human observation and professional judgment.

3. Would I stand behind every sentence if the person asked me about it face-to-face?
AI can produce persuasive language, but leaders remain responsible for every word they send under their name.

Responsible AI use requires more than accurate output. It also requires ensuring that the human judgment and relationship represented by those words are genuine.

Where authenticity lives

This brings me back to my friend.

Perhaps his boss did use AI. I do not know.

But AI did not observe his work.

AI did not decide that he deserved greater responsibility.

AI did not choose to promote him.

His boss did.

If AI helped his boss find better words to explain a judgment he had already made, perhaps those words were not less sincere because a machine helped shape them.

The value of his promotion was never in the syntax of the letter.

It was in the human judgment behind it.

As AI becomes increasingly embedded in professional life, authenticity may need a slightly different definition. It may no longer be particularly useful to ask:

Did a human write every word?

We may need to ask instead:

Did a human do the thinking? Did a human make the judgment? And is a human willing to stand behind the words?

That is where authenticity now lives.

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