Well, that's the problem right there. An estimate is not a promise. It should not be treated as such.
If he really needs an estimate he'll tell me to start digging into it right away, and I'll let him know after a bit of time how it's going. If there are still large uncertainties and my boss still wants this completed by some specific date, we might try to explore alternative solutions.
In the above case, I didn't get that time I would need, they wanted the estimate to include that time I would need to dig into it. But that's above my estimation powers. I didn't even know if what they asked was possible at all.
They went and asked someone else who did guess some number of weeks, but the work never got priority so we still don't know.
Yeah that ain't gonna fly with me.
Did you say that
1) Without knowing further best case is it takes N time, worst case M time, and if there are certain obstacles it could be completely unfeasible. 2) To get more accurate time and to understand whether it's feasible I would need O time to figure that out first, and I can give you the more accurate estimate then.
The problem is when we assume everything is a known. I try not to do that and I try to set that expectation with my manager. If everything had an easy answer we wouldn't need highly paid problem solvers.