I’ve been checking out Joel since you turned me on to him awhile back. Can you elaborate a bit on the “significant advantages?”

My experiences as a fledgling project manager / architect / lead have been wrought with disaster in the project planning arena. Here’s the dilemna I’ve been dealing with constantly for the last 5 months on my project:

We plan a Release. I’m working with a .NET dev shop in Mexico and I’m not completely sure about their capability. I have to guess about how long things are going to take to implement. My track record seems to be that my estimates are always low by about a factor of 3.

Here’s the issue. I give my development plan (which is already off by a factor of 3) to my project management folks. They say “jeez, the customer won’t accept this … it’s too long.” Then they wheedle me and ask if I can somehow pull a miracle to meet a date that’s more palatable. I have to do this if I want to keep my job. So we go back to the drawing board to meet some insane request. We can’t refuse, because we have mouths to feed at home.

The team works 75+ hours a weeks, and I’m stuck in MX for weeks at a time without going home. The inevitable happens. There’s no way in hell that we can meet the schedule. Eventually we go back to the customer and tell them that we’re going to be late. The customer freaks and then calls the president of my company, who tells the customer that we’ll never slip a date again … and gratuitously makes another ungrounded promise about when something will get delivered.

And the cycle repeats. Over and over again. On this project, the cycle has happened at least 8 times since January. The higher ups keep making promises, but they are not here on the ground doing the work.

There are lots of places where the above drama could be averted. I think the most critical are: I need to get much better at estimating time, or add a ton of slack to my schedules … and I have to get firm and tell the folks that pressure me to reduce my schedule that they can pretend that it will be done on their date but I’m going to keep pointing out my original date (WITH the added slack time … and I’ve got to stop worrying that it looks like WAAY too much time — my track record says that things always end up taking longer) whenever they complain about schedule slips (ala Joel). I’m ready to do this, but know that it’s going to go over like a lead balloon.

Any sage advice?