I’m going to have to tell my boss today that the stuff my squad has been working on is going to arrive late. To much needs to be fixed or reworked, and there is one or two things that have been missed alltogeather.

I think the biggest problem is that the thing we’ve been working on got into testing far too late — only a few days before the deadline — meaning that there was no time left for fixing things. Really, you can draft all the plans and designs you want but you really don’t know how well it will perform until the “working” code has been handed to someone else.

Another problem might have been that I didn’t push for more time upfront. It’s been difficult to do this in the place I’m working now. It’s almost like they’re on to me (or at least have their own ideas of when things should be delivered). But I’m guessing it’s still heaps better to shatter expectations by saying something will take longer upfront, then get it delivered early, rather than be optimistic about it and come up against the deadline. “Underpromise and overdeliver,” they say.

I wonder if there’s a way to have two deadlines: one the business knows about, and one for the squad. The first one is quoted to be a respectable amount of time that is significantly larger than what you really it would take to deliver the feature. That would check expectations, and leave enough time for any rework. The second is a more optimistic deadline for the squad to work towards. I think having this second deadline is important, otherwise all the work will pile up near the end of the first one and you’ll deliver late again. It’s all so deceptive though, and the thing is that you almost need to deceive yourself: you know that the second deadline is not the “real” deadline after-all.

I don’t know. I find all this estimation and managing expectations quite difficult and it’s generally not something I like doing.

In any case, we’re going to need more time. I guess I can take solice in the fact that we almost got there, maybe 70-80%. We just need to get that other 80% over the line.