I've been developing software for over 20 years, and I still can't estimate how long something will take me when I've never done it before. This uncertainty needs to become more than just a stick to beat developers about the head and shoulders with. Most of the time the PMs understand this, but there have been many projects where they just don't get it. I have suffered great anxiety from being forced to give estimate…
>That's when I knew it was time to leave that team Currently in that situation. My "agile" estimate blew up by a factor of as much as 10, just because the ask was conceptually very simple, even to the domain experts I consulted. And by bad luck the way I was implementing the story it happened that the issues unfolded one-at-a-time, rather than somewhere in the beginning where we could have broken things up into more…
Shit happens. The end of a sprint is there to highlight issues like this so the business side can re-evaluate if continuing is still a good idea.
I don't want anyone on my team working nights and weekends to finish a sprint task (system going kaput is the only time I would reach out for help). Anyone letting their team work normal sprint tasks on nights/weekends is not going to keep their team very long. They will either quit or burn out and stop working.