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estimation vs. delivery

My Journey in Software Estimation - What a long strange trip...

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My Journey in Software Estimation - What a long strange trip...

I’ve had a long career with estimates in software projects. While it’s been a rocky journey, I now feel that I’ve gotten to the point where I truly understand how to and the value of estimation.

But before I give you the great reveal, let me share some of my history…

Estimate Newbie

I first began my career as a newbie in estimation. I fell into the trap of being as honest as a could be and I found that my estimates were often used against me. For example:

  • My bosses would often forget the “fine print” around the estimates. Words like – “this is only a guess until I get more formal requirements. Or, I’ve never done this before, so I really don’t know how long it will take” were never remembered. Imagine that?

  • People who had not a clue would weigh in on my estimates. Bosses, who were under pressure to release quickly, would cut them. And project managers, who were trying to “defend” the project, would pad them. And my developer colleagues, who always had an optimistic spin on things, their estimates would always be lower than my own. Imagine that?

  • And I always felt that nobody wanted the “truth” in estimates. That they couldn’t handle it. So, it negatively influenced me to pad/cut depending on the situation. But the key point is the inherent dishonesty I felt around all estimate discussions. Early on, it felt like a game of sorts. Where the last one that weighed in on a number…won. And the development team…generally lost. Imagine that?

But as in all things, I grew in my experience and in my career. Soon, around the late 1980’s, I became a “manager”. Which meant that I not only had to estimate for myself but for my group(s) as well. This showed me both sides of the estimation continuum and frankly, I didn’t like it much.

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