A colleague sent the email she had been building toward for months.
Clear expectations. Specific next steps. Everything she needed one staff member to finally hear, written down in one place.
What came back was a reply. Polished. Complete. The right length, the right tone, every box checked.
And generated by AI. She could feel it right away... the smoothness where the friction should have been, words that technically answered her email without ever truly answering it.
Months of conversations built up this moment, and the response told her nothing about whether any of it had landed. So she asked me the real question. How do you lead someone who will not put in the reflection time?
The task was the thinking
I told her this first. The reply was never the thing she needed. What she needed was evidence that this person had sat with the feedback and turned it over, and the email was only ever the container that evidence was supposed to show up in.
But she sent that ask in an email. And “respond to this email” is a task software can finish in nine seconds.
So it did.
The staff member may not have skipped the assignment out of defiance. They may have genuinely believed the assignment was to send something back. (Most people have never been told that the point of a reflection is the reflecting, not the artifact. Go figure!) The deliverable got completed. The work it was supposed to represent never happened.
Some work cannot live on the page anymore
This is the part that shifted for all of us this year, quietly, and most leaders have not adjusted for it.
Anything you can request in writing can now be returned in writing with no human mind in between. When the written response is what you are grading, the person can step out of the loop entirely and you would never know. You end up assessing their software and calling it their work.
So you move it.
Reflection you need to witness has to happen somewhere it cannot be generated for them. A conversation. A question you did not send ahead. A “walk me through your thinking on the second point” that has to be answered in the room, in real time, with you watching them find the words.
You cannot outsource your way through a conversation. That is the entire reason it works.
A generic reply is still information
She had been too frustrated to see it, but that email was still telling her something. It was data.
If she names it plainly, “this read as generic, and what I need is your actual thinking, not a polished response,” one of two things happens. Either the person engages, and she gets the reflection she was after. Or they do not, and the disengagement stops being a feeling she carries around and becomes a pattern she can point to.
Even the second outcome is a win. A vague frustration has turned into something she can name, and that is the conversation finally getting honest.
The reframe
Leadership is partly a question of where you put the work. Put reflection somewhere it can be handed off, and someone, eventually, will hand it off. The move is to stop accepting proof that was never theirs to give, and to put the thinking somewhere only they can do it.
A question for you
Where in your leadership are you accepting the deliverable, when what you actually needed was the thinking behind it?
A small ask, if this resonated.
The leaders who read this newsletter tend to know other leaders who would read it too. The people quietly doing the work. The ones who think carefully before they speak. The ones who notice what the room missed.
If someone like that came to mind while you were reading, send this their way.
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