I will try to list out all the breakdown of the task, using use cases.
I will include all the sunny path & rainy path (when something goes wrong, what should we do)
Remember, listing down those alternate course (rainy path) is very important, because more than 50% of our time spent on it.
Most of the time, our superior only consider sunny path (take for example, login system, they will think they login system is basically user key in username & password, and they expect you to finish in 5 mins, but they never consider, what if user key in wrong, or do something funny). It our job to let them know the alternate course, and the time it takes.
Negotiation always need mutual understanding.
After giving the realistic estimation, you just try your best to achieve it. I won't suggest you work around the clock, just because you superior has a bad estimation. Just do it at your own pace, which won't affect your health.
Perhaps another alternative is, try advise him to drop certain features. This is one of the techniques used in Agile methodology. Focus on must-have feature first, and try to include the good-to-have features in the next edition.
Summary:
- show him the breakdown of the taskn and time estimation for each of the subtask. Don't simply tell him "I can't do" without anything back you up. It will makes you look bad.
- advise him to drop those
good-to-have features.