Apologies to Management

Management at my company hates me for being likeable. Many of them are my friends. My proudest moment was when someone said to the director “that guy is really, really smart, isn’t he?” to which she replied somewhat ironically, “yeah, we’re trying to rein that in.” She has since quit, but her replacement feels the same way about me. As does my new supervisor, who has often invited me out for drinks.
Earlier this week, management had a closed-door meeting discussing the possibility of requiring employees to work over Christmas vacation. Most employees didn’t pick up on that message, but I know how to read people, and I knew it was a consideration. I sent an email to the entire department, proactively warning of the dangers of making such a request, and at the very least, if the option is on the table, to come out and say it now, instead of dropping it on people the week of Christmas.
As it well should, the email caused an instant panic. Many of the more resigned employees laughed it off— not because they didn’t think it would happen, but that they would expect no better than to have Christmas cancelled. The newer employees started looking for the signs that it was an option, and started seeing them.

My boss called a meeting with me.

He started the meeting with explicit instructions: this meeting was purely for documentation purposes, to record that I had been made aware of the company’s email etiquette policy. He listed the reasons why the email was not appropriate. He asked me, as he is bureaucratically required to do, what my side of the story was. I gave it to him, he wrote down his notes, and then gave the response that the director had already fed him to give. I pushed back, pushing him to tell me outright if cancelling Christmas was being considered, and he replied, “that’s a fair question, I’m just saying that’s a question that you relay to me, not replying to the whole team.”
“Well, I think we’ve resolved the communication issue. I will parlay all grievances to you directly. I’m giving you one now– I’m not speaking for myself; I’m telling you as management, our department can not afford to rely on employees coming in on Christmas.”
“That’s a valid concern,” he reiterates, “I just want you to understand that you need to bring these to my attention, and not to the team.”

I really like the guy. I specifically asked to work with him. But this isn’t personal. This is me, the employee, fully aware that what I tell him is going on record. I say it again, as my concern had not been addressed.
“I am not saying this in my own defense, nor as an individual employee. I’m asking on the behalf of the team, has the planning been put into action that if we do not provide the results you need, that it will be demanded that we work over the holidays?”

He looked down at the table, mumbling almost incomprehensibly, “okay, it’s just how you communicate it.”

He looks up at me, begging me with his eyes not to do this to him. The meeting was a policy-mandated reprimand, not him criticizing me personally. But I'm not attacking him personally either; I'm attacking management. I just wait for a response. Finally, he meekly closes his book and says, “okay, I’ll send you a write-up of our meeting for the records,” and stands up.

Sorry Chris, it wasn’t personal. For what its worth, I’ve stood up against nearly every authority figure in our department and never once reached an accord. I understand why. The fact is, they’re just here because it’s a living. Words matter, and when I criticize management, it hurts.

He made it very clear how much it hurt for the director to read my email, outright asking her, “are you planning on taking away Christmas?” She never wanted to be that person, and still doesn’t. He never wanted to be the guy on his side of the table, reprimanding someone for standing up for what he thought was right. But he is the guy on the other side of the table.

His job as a supervisor is to keep me quiet, and I respect that. My job is to speak out, and I take pride in my job.