Triangle Estimates

I estimate using time, not points. I do this even though I have mostly worked on product development teams inside of companies and not as a contractor for clients.

But, estimation on product development is not as high-stakes an activity as it is if you are billing based on it. The judgement of a successful product development project is based on whether it moves some business needle, not whether it was under budget. The margin on successful product development dwarfs reasonable overruns. There is also a lot of appetite for risk, where we know that we’ll win some and lose some.

That’s not true if the work is for clients. If they pay by the hour, they expect the estimate to be accurate. But there are very few (if any) big software projects that can be accurately estimated. When you’re wrong, you either have to eat it or have a very difficult conversation.

I don’t have a good answer, but I would start with triangle (or three-point) estimates. To use them, you estimate a most-likely estimate and then a best and worst case on either side. The three numbers describe a distribution (see the wikipedia page for how to combine them). The result is an estimate with a error range and a confidence interval. I would recommend sharing that instead of a single number.

The only task management system that I have seen that offers this option is DevStride, which carries three-point estimates throughout its system.