Always Multiply Your Estimates by π (2013)

People tend to want to hear or give the shortest estimate that seemingly sounds feasible.

I don't do that anymore. I try to push estimates as high as possible and then collaboratively cut down on requirements/promises/features to match an expected (time) budget.

This often leads to more pragmatic work items and sensible prioritization from the start. And it is an opportunity for general communication and understanding the value of things.

My theory is that this has to do with our difficulty dealing with delayed gratification.

Tell people a short number now = immediate praise, long term pain.

Tell people a higher estimate, immediate negative; finish in time = delayed gratification.

I agree but you can often miss out on work if you do this as a freelancer.

Last potential customer I spoke with I did this. They were insulted by my estimate and practically hung up the phone on me.

We can't read the mind of that potential customer. Did they want cheap, fast labor? Probably. Do you optimize for that? I assume not. You might have dodged a bullet or maybe there was a communication issue.

I will sometimes give an estimate in multiple ways -- "This takes about four weeks for the engineering work, but unless we remove all other priorities it will take about 3 months to complete."

A lot of the time when you are working the delays aren't just the uncertainty of an individual task; it's that you're working on several projects at once, you're attending meetings, etc, so that you might only average 2 hours / day working on a particular task or you might not be able to start a task for several weeks (depending on whether you work sequentially or in parallel).

You still need a realistic, achievable estimate for that first time, in case management calls your bluff, but distinguishing between "the amount of effort this will take" and "how long it will be before it is complete" can help set realistic expectations while making it harder for management to mistakenly think you need two months to complete a task that could be done in two weeks.

Oh yes, the ETA should always be significantly higher than the work estimate. I sometimes say I work in my sleep.