My response to estimating is that if you want anything accurate I’ll need time to estimate - roughly 1/4 of the estimated work should be spent estimating.

As a rule of thumb, if the work is estimated to be a day then is should take me 1/4 day to estimate. If two days then half a day to estimate. If 4 weeks then 1 week to estimate.

We normally continue with guesses that are meaningless.

What would you do if they actually gave you a week to come up with an estimate? Start drawing Gantt charts?

1/4 seems reasonable for a day or two, but I dunno… it seems like there must be some constant factor?

I’d draw a lot and probably prototype as well - I suppose the main thing is that we never get to that as we estimate but don’t do “big design upfront”