9 tips for estimating software project proposals

Alan Tai
11 min readAug 5, 2022
Tom Hanks and the fortune teller machine in the movie “Big” (Source: 20th Century Studios)
Tom Hanks and the fortune teller machine in the movie “Big” (Source: 20th Century Studios)

QuickDraw is the 2D graphics library written entirely by Bill Atkinson in the 1980s. Andy Hertzfeld considers it the single most significant component of the original Macintosh technology. It consists of a total of 17,101 lines of code in assembly language. During a magazine interview, Bill remembered that he worked on it on and off for four years. Steve Jobs told the magazine reporter that it was 24 person-years Apple had invested in QuickDraw.

MacPaint (Source: https://www.computerhistory.org/)
MacPaint (Source: https://www.computerhistory.org/)

Is that how we cope with the impossible project deadlines due to poor estimates which are sometimes off by a factor of 3 to 10? How could we estimate more accurately such that we don’t have to hire 10x engineers to rescue the project?

All software project proposals I helped to create involved a certain degree of risk and pressure. The risk and pressure come from multiple sources — the business environment is chaotic, the project schedules are so compressed, the budgets and people assignments are so constrained, and at the same time, we want our offers to be as competitive as possible. For Software Engineers who are asked for the first time to provide estimates for a project proposal, it is like being asked to overcome…

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Alan Tai
Alan Tai

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