Ran across an interview at InfoQ about using poker playing to help with software estimation. Looking at the planning poker site, it seems a bit gimmicky and hokey and reminds me a lot of the the CRC cards approach (BTW, I think my next job title will be agile consultant). I have never really done a project using CRC but I don’t think that I, or most of my co-workers, would have the patience for it. Same thing goes for the poker planning idea.
I’ve never found getting estimates to tasks to be that big of an issue when planning projects. If you can break tasks down into reasonably sized chunks, I find that good developers are usually pretty good at determining how long it will take. The big problem with planning projects is trying to prioritize tasks and determine what needs to go into each release, not so much the estimation of how long it will take.
All that being said, I think Tim McCune would love it. Maybe he can get Yahoo to adapt it.