You find out from the calendar invite. Your manager committed the team to a date in a meeting you were not in, and now there is a kickoff Thursday for work you know takes eleven weeks. Two options are already forming in your head, and both are bad. Say nothing and burn the team, or push back and get filed under difficult.
Managing up gets read as flattery, and the version I teach is closer to translation.
Half of the relationship is your job
John Gabarro and John Kotter wrote the piece that named this problem in 1980, and Harvard Business Review has been reprinting it ever since under the title "Managing Your Boss" [1]. Their argument was that the relationship is mutual dependence between two people who both have limits, and that half of the work belongs to you. You are expected to understand your manager's goals, pressures, and working style, to know your own, and to build the relationship on both.
Leaders decide in four currencies: revenue, cost, risk, and speed. If your update does not touch one of them, it drifts past them no matter how good the work underneath it is. That is the whole skill, and it does not require you to agree with anybody. It requires you to say the true thing in the language the decision gets made in.
Read the history before you spend credibility
Before you spend credibility, read the history. Amy Edmondson's 1999 study in Administrative Science Quarterly looked at 51 work teams inside a manufacturing company and introduced a term that has since been flattened into a slogan: team psychological safety, a shared belief among team members that the team is safe for interpersonal risk taking [2]. Her finding was that teams with it engaged in more learning behavior, and that the learning carried through to performance.
The part that matters for you is that it describes a property of the team, not a property of your nerve. Whether the last three people who pushed back at your company are still in good standing is evidence, and you are allowed to use it to decide how much to spend and how fast.
Bring the trade-off, not the objection
When you do push back, bring the trade-off instead of the objection. "The team is overwhelmed" is true and it will lose, because it is a statement about your team, and the person across from you is managing a company.
The phrase I put in the Power Phrases library for exactly this room is one sentence: the trade-off is speed versus alignment, and I recommend this option because it keeps us on strategy without slipping timelines. Name the trade-off, name your recommendation, name the reason. That is the same objection with a decision attached, and it lands in a way that "the team is overwhelmed" never will.