Earlier quoted context omitted.
One thing I’ve found to be helpful is to make it clear that I won’t be mad about a long estimate If that’s how long it’s going to take then that’s how long it’s going to take. I think there’s a group of people who are used to getting lots of pushback on their estimates and so they estimate low to avoid that conflict. The future conflict of things being late is not something they have to deal with right now and maybe…
> I won’t be mad about a long estimate So... my experience with this mindset is that you won't be mad , but you'll just say "that's too long/expensive" and cancel the project entirely. Then the same project will come up again in two months with different wording, again and again, until I give you the estimate you think you can afford. And then the thing will end up taking longer than the original "too expensive" esti…
The biggest issue I have is developers making business decisions without realizing it or without saying it — saying no to something because it would take too long or be too expensive, without first asking how much time/cost can be consumed
The same occurs with estimating — they’ll give a risky estimate instead of a safe one, because they’ll unilaterally decide the stable one is unacceptable; and not bother mentioning this with their estimate, or knowing what the rest of the timelines look like.
The other half of the problem is that people tend to only want to give one number (and people typically ask for a single number), but what you really want for project planning is the median +- margin of error timelines. The 1x,2x,3x rule is just a hack to work around that unwillingness.