I'm trying to do you all push back on unrealistic deadlines without sounding difficult?

I push back by offering options and risks instead of a flat no. I'll say, "I can start today. Based on similar work, this takes 12 to 16 hours to do well. I can give you a draft with the key points by end of day, and the polished version Tuesday. Which do you prefer?" If the date must hold, I spell out the tradeoffs in plain language and ask for a decision. For example, "To hit Friday, we'd need to drop the deep analysis and limit QA, or add another person. Are you okay with that risk?"

I also ask what is driving the date so I can target the must haves. "What absolutely has to be in for the meeting, and what can land next week?" Then I surface priority and capacity, not attitude. "Happy to hit Friday if we pause X and Y, or if we can get Sam for four hours. Which should we deprioritize?" I follow up with a quick written recap so expectations are locked. "Confirming plan: draft by EOD with sections A and B, full version Tuesday, and we'll skip C unless we add help." This keeps the tone cooperative while making the cost of rushing visible and giving them a clear choice.

I babysit the family photo hoard and learned the pattern the hard way. At work I say, "If we want Friday we only ship the album with no captions. If we want the full set it is Monday," and I keep repeating that until someone picks. Then I write down what we picked so no one argues later.

The thing that saved me is framing tradeoffs like a custody schedule for work. I say, "To meet Friday, I can deliver A and B by Friday and C by Wednesday, or we move all to Tuesday. Which do you want?" If they insist on all by Friday, I ask what to drop or who they can lend me for help. I write a quick recap so no one forgets what we agreed. When I did not do this, I missed both the deadline and bedtime, so now it is nonnegotiable.

Right now I push back by showing the math. I say, "To hit Friday, I need 12 focused hours. Current scope is about 20. We can cut X and Y or move to Tuesday. Which do you prefer?" Then I stop talking and let them pick. Calm and factual works better than pleading.

Learned it the dumb way. I once swallowed a Thursday deadline and ended up hot gluing a prop at 3 a.m. while my cat ate the mood board. It looked fine in photos but it cracked during the meeting and we had to redo it anyway. Now I say, "I want a win, not a fire drill." "If we keep the date, quality drops here and here. If we keep the quality, the date moves to Tuesday." I follow with a short recap email so there is a record. Most people respect numbers and choices.