My favorite question: "Is the date slipping, or has it slipped?" What you really need to do is help the person setting the deadlines plan. There are things the

My favorite question: "Is the date slipping, or has it slipped?" What you really need to do is help the person setting the deadlines plan. There are things they're doing that are synchronized with finishing the project, and there are things that simply depend on the project. Marketing may want to publish a blog post. Sales might want to promise a delivery date (or already has). Management might want to claim victory for a Q3 delivery. All of these things are outside your knowledge, and they're frequently based on your initial estimate. So, over-communicate, but also slip once, and slip hard. If you're a week out, and going to miss by a day, slip the date a week. Fuzzy, frequently communication isn't useful, because nobody can plan around that. Make sure you are clear about the moment in time you want the project manager to go from "I'm worried about date X" to "We've change the date to Y", because while it's fuzzy in your head, it needs to be clear in theirs.