How do you all push back on unrealistic deadlines without sounding difficult?

The trick is to turn pushback into options framed by data. When you get a two day request, reply within the hour with a brief estimate, the minimum viable scope you can hit, and the risk of keeping the date.

Example: "For the homepage refresh I estimate 32 hours total across wireframes 10h, visual design 12h, review 4h, iteration 4h, handoff 2h." "With two days across time zones I can deliver annotated wireframes and a baseline style by EOD Friday, with responsive states and final polish by next Wednesday." Follow with a question that asks for a decision: "Do you want the two day version, or should we move the deadline to get the full scope?" That keeps you neutral and makes your manager own the tradeoff, and a short Monday capacity note helps prevent surprises. Use this email template: Subject: Scope and timeline options for [Project]. Body: I have [X] hours before [date and time in UTC]. Full scope is about [Y] hours covering wireframes, visual design, review, iteration, and handoff. Risks of holding [date] include quality drop, rework, and missing asset lead times. Our printer needs three business days for proofs, and courier pickup here closes at 3 pm. Option A delivers [reduced scope] by [date]. Option B keeps full scope by [later date]. Please confirm which you prefer so I can plan dependencies and, since I do not have client access, can you communicate the choice to the client?

Stop negotiating against yourself. Give a time-based estimate and a scope-based alternative. Name the risk in one line. Keep it about outcomes, not effort. Call out the timezone math so two days is one and change.

Example email: Based on the current scope, the earliest delivery is next Wednesday. If we must hit Friday, I can deliver screens A and B with placeholder copy and move C to next sprint. Risk if we force full scope by Friday is rework and defects, which will push the following release. Please confirm which option you prefer so I can prioritize and notify stakeholders. Since I do not have client contact, can you relay this framing to them and loop me in on decisions?

Back when we burned comps to a CD and FedExed proofs, the deadline magically included shipping days. We learned to say the quiet part out loud. Try, I need X days for quality and approvals, otherwise we ship a coaster.

Set boundaries kindly and though they might still press your time.

It's tough out there and but pushing back usually just brands you as the problem without fixing anything.

Been there. After my split I had to start timeboxing work around custody days, and the only thing that stuck was blunt tradeoffs in writing. I send a calm note that says what fits, what slips, and what breaks if we pretend the calendar is elastic. Half the time they still push, so I add the part where I will stop at 6 and pick it up tomorrow. Exact words I use: To hit Friday, I can deliver X and Y, but Z moves to next week or goes lo-fi. It is not negative to say doing everything means doing nothing well.

Back in the day, we'd develop film over a week and nobody complained about rush jobs. These days, I tell my boss, hey, if you want it fast, good, or cheap, pick two - can't have all three. Makes 'em chuckle while getting the point across.

Start by documenting everything. Track your hours and the actual time tasks take and then present that data when deadlines come up. Use phrases like "Based on past projects, this would typically require X days to ensure quality." That way, it's not personal, it's factual.

If your manager keeps agreeing to tight turnarounds, suggest a quick call to clarify scope before committing. Say something like "To meet this deadline, we'd need to cut features A and B - does that work?" It puts the ball back in their court. And always follow up emails with a summary of agreements to cover yourself.

In my experience, if this persists, it might be time to look for a place that values realistic planning. Small teams can be great, but not if they're chaotic. Protect your boundaries or burnout is inevitable.