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I think the estimate I'll give depends on who is asking. When my boss asks how long something will take, I lowball it, because if I gave myself plenty of time in the estimate, it might sound like I'm planning to work really slow. There's not much risk in underestimating, either. It's easier to ask for more time once you are half done with something. The fact that you're already half done puts you in a stronger position.

I think I can estimate much better when I feel free to say any number at all, that I just don't know, or even that the project is not worth doing.

I don't think managers should take estimates at face value, but consider the tone and the context and make their own estimate. Or, perhaps, not ask the employees to do their own estimating at all. It seems like the burden should be on the manager, and he/she may have to be creative. At my last company, they were crazy about making developers estimate every little thing, and it created an oppressive atmosphere that contributed to me leaving. For the reasons in the article, accurate estimating is almost the same as doing the work itself. And the estimate feels like a promise, one made without complete knowledge and in awkward circumstances.

"I tend to make pretty good estimates in my own consulting for two reasons: I usually bill on a "not to exceed" basis and I keep really good records of how long things have taken me in the past."

You have every incentive to judge accurately, because there is tremendous risk in making a commitment with too much uncertainty. You'd be better off not signing a contract than risking a wildly optimistic estimate, so naturally, you're only going to take projects where you can estimate pretty well.



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