> this feels like it suggest you just fall in line with the upper management while providing lip service to the plebs. As an IC I’ve always despised managers who’d be a very sympathetic ear in 1:1s but always be “part of the system” when it mattered the most

You're "part of the system" the moment you sign the employment contract for a manager position, this is literally your job to fall in line with upper management. As middle manager you can and should raise concerns to higher management, but once they take a decision, you have to apply it. Being empathetic is not playing both sides, manager's job is to apply upper management decision even if you don't fully agree. And you don't have to pretend in private to agree on everything, no one will buy that.

> manager's job is to apply upper management decision even if you don't fully agree

That is not at all true. The manager’s job is to manage employees in a way that is in the best interests of the company. I’ve met plenty of leaders through my career who are successfully able to shield their employees from an incompetent management. That is part of the job.