Even if you update the estimate based on data, too many managers still want to know, “When will it be done?” Emphasis on done.
And, while managers might not remember the assumptions you offered with your estimate, they remember that date. I find that maddening.
However, while I tend not to like estimates in the small, I do like ballpark estimates or gross estimates. And, I've changed how I refer to those kinds of estimates.
I now use the word forecast.
Everyone I've met understands weather forecasts. They understand the forecast for the work close in time is probably more accurate than the work farther away. I don't have to explain my date ranges.
I'm not sure why estimates anchor people's expectations. I'm not sure why they appear to not understand probabilities. However, this is my experience.
I'm not going to blame people for being human. I'll change my words to get a better outcome and manage risks m ore easily.
That's my experience: estimates anchor people's expectations. Forecasts appear to include uncertainty.
If I can have a better conversation about the uncertainties, I'll take that every time.