As Principal Web Developer at Stack Overflow and a long time Tech Lead, I learnt that accurate estimates were essential in order for a company to be healthy and productive. Over the years I have spent a good deal of time developing my theories for why estimates and breakdowns are so important, and crafting my own methodology for how best to go about doing them.
Below, I attempt to distill the lessons I’ve learned so that others can experiment with and improve upon my techniques. Now, I should be clear, the advice below is what works for me. I’m sure there are different approaches that might work better for others. Feel free to share your favorite approach in the comments. …