Earlier quoted context omitted.
"How long will X take?" "I don't know, I've never done X before." "Yeah, yeah. It doesn't have to be perfect analysis, just a rough idea for scheduling. Not written in stone, ha ha." "Uh, a week?" "Okay, great, so if I say 8 days you should have it done by then?" "Yeah, I hope so." "Great, thanks." Day 3: actually doing X requires unforeseen Y and Z which will each take a month. "We need to add Y and Z to the schedul…
"A week" is a terrible estimate for complex things that have components that you can't foresee. If you lose "a day" on some problem outside of your control (compiling starts to fail and it turns out someone checked in some code into your branch by mistake), you've basically wasted 20% of your estimate. Never say a week when there's the chance something will require a month because you didn't understand it. You need t…
"I don't know why, but I don't feel comfortable guessing less because I don't fully understand X."
"Okay, that's not a good way to estimate. Why don't you spend some time to come up with a plan for X and we can estimate it after that. When can I have the plan?"