Why are developers expected to estimate tasks at all?
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This management tendency is the worst part of being a developer. Software development is not carpentry. Almost everything a developer writes is unique, they have never built that particular thing before. We are not cabinet makers repeating a variation of something we've built hundreds of times before.
In my ideal world, management would simply tell me which task they want me to work on next and then as it proceeds ask for a regular update of what percentage of completion it is at. It would then be the manager's responsibility to extrapolate my likely completion date, learn my accuracy over time, adjust to it and manage expectations of upper management.
If developers have to be the ones carefully calculating estimates and managing expectations then there's really no purpose to middle-management. The developer might as well be speaking directly to the client if the only value added by managers is to pass estimates from one hand to the other and then brow beat developers when things don't work out.
