Estimation is really hard, especially if you're dealing with new challenges, new people, and new expectations. Throwing moving targets (unplanned changes) into the mix, as you noticed, makes estimation even more difficult.
The thing is, it very rarely is the case that a wrong estimate will sink a project. Things get delivered late all the time. No one dies. Most stakeholders aren't like two year olds throwing a tantrum because an unforeseen problem delays a deliverable by a few days (admittedly some are close).
The actual definition of failure also needs to be considered. Is it considered a failure because a project manager ended a colored gantt bar at a particular date and the actual time was longer? Or is it a failure because the customer cancelled the contract because a deliverable was not available on the agreed-upon date? Or is it something far more nebulous, like a slow death march towards a misguided goal that burns everyone out and compels them to sip artisanal coffee and daydream about leaving instead of grinding onwards and hitting targets?
Ultimately, people "don't care" because accurate estimates are not the most critical problem on their mind. Most of the time an accurate answer to "When will it [the deliverable] be done?" has about as much gravitas as guessing the number of jellybeans in a jar at a kid's birthday party.
Doing a retrospective and analyzing what went wrong when a project delivery slipped expectations is certainly reasonable but it so easily slips into a blame storm and/or people making commitments that aren't realistic. Getting straight answers from folks for this kind of analysis requires a level of psychological safety that just isn't present in most workplaces.
Internal estimates are a political tool, not a technical, financial or scientific one: First, decide if you want to do it or not. Then do the estimate, high if you don't want to do it, low if you do want to do it.
Any kind of reality doesn't factor into it.
In the Word example, somebody really thought this project was worthwhile for some reason, so they gave a very low estimate to get things started. As soon as money has been spent on a project, it isn't likely to be cancelled as easily, so you are safe to continue even if you exceed your original estimate. In the worst case, you need a few excuses.
External estimates, i.e. estimates you use for writing up a contract with an external customer, are different. Those actually do matter, depending on the wording of the contract. But a smart contractor will try to get the contract into a shape such that the above for the internal estimate does apply.
Estimation is really hard, especially if you're dealing with new challenges, new people, and new expectations. Throwing moving targets (unplanned changes) into the mix, as you noticed, makes estimation even more difficult.
The thing is, it very rarely is the case that a wrong estimate will sink a project. Things get delivered late all the time. No one dies. Most stakeholders aren't like two year olds throwing a tantrum because an unforeseen problem delays a deliverable by a few days (admittedly some are close).
The actual definition of failure also needs to be considered. Is it considered a failure because a project manager ended a colored gantt bar at a particular date and the actual time was longer? Or is it a failure because the customer cancelled the contract because a deliverable was not available on the agreed-upon date? Or is it something far more nebulous, like a slow death march towards a misguided goal that burns everyone out and compels them to sip artisanal coffee and daydream about leaving instead of grinding onwards and hitting targets?
Ultimately, people "don't care" because accurate estimates are not the most critical problem on their mind. Most of the time an accurate answer to "When will it [the deliverable] be done?" has about as much gravitas as guessing the number of jellybeans in a jar at a kid's birthday party.
Doing a retrospective and analyzing what went wrong when a project delivery slipped expectations is certainly reasonable but it so easily slips into a blame storm and/or people making commitments that aren't realistic. Getting straight answers from folks for this kind of analysis requires a level of psychological safety that just isn't present in most workplaces.