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When we praise and glorify the team working late to meet speculative estimates, we destroy life and corrupt the culture of the company.
Just start referring to “estimates” as lies. “How long will that take?” “Well, if I had to lie, a week?”
Alternative to estimates: do the most important thing until either it ships or it is no longer the most important thing.
Kent Beck
In preparing for [projects] I have always found that [estimates] are useless, but [estimating] is indispensable.
General Dwight D. Eisenhower
It’s better to be roughly right than precisely wrong
Maynard Keynes

We keep on estimating and planning according to those estimates, expecting to meet deadlines and firing the wise fools that question the practice, and report the actual numbers that are not accepted by management. However…

Insanity: Doing the same thing over and over and expecting different results.
Albert Einstein
Ask, “Is the estimate useful?” rather than “Is the estimate right or wrong?”
Chris Matts

Watch out for:

Estimates become targets.
Esther Derby

Use yesterday’s weather, which implies “results from the past give guarantees for the future”.

Collect metrics about the real system, like average lead time distribution, cumulative flow diagram, average throughput, and predictability.

Thou shalt not treat estimates as commitments.

Setting deadlines and promises based on estimates is dysfunctional.

The problem with estimates isn’t so much the concept of estimates themselves—because they are fine if we know that they are estimates—but that the way we treat them in software is not like an estimate. They drive deadlines and they drive promises and because of this, we get all kinds of problems.