
Source: Wikipedia
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Planning poker, trademarked by Mike Cohn, is a modernizing of a 50+-year-old estimating process known as Wideband Delphi. Estimating is not far from the dark arts, and attempts to make the process serious and exacting are ill advised. James Grenning devised planning poker as a quick and entertaining way to come to consensus on estimating stories in agile. I've found it can help dramatically minimize the tedium of estimating through a large stack of stories.
A typical point scale might be 1, 2, 3, 5, 8, 13. Resist larger scales--toss the higher-value cards. You might replace them with one card that says "too big."
You might want to include a few additional cards: 0, ? ("I don't have clue"), and infinity. The value of adding a 0 card is debatable (nothing is free, and even if development is "free," testing a story is never free), but you may find some usefulness in having it: Sometimes, completing one story automatically includes another. Or, a story might simply represent a milepost achieved.
The wikipedia site provides good detail on the steps involved, but I highly suggest you make your own rules and stick to them. The section on anchoring is particularly useful: part of the reason James devised planning poker was to counteract the heavy influence on estimates coming from one individual. Make sure that when people divulge their card selection, they aren't watching and waiting on certain other individuals to show theirs first!
Before starting the meeting, figure out how long you'd like to spend estimating. If your backlog of stories looks pretty good, and there's a good understanding of the project by most people in the room (obviously not always the case), you might find that 5 minutes per story works well. Appoint a facilitator who can keep time and help keep the estimating session on track.
If the product you're building is less well-known to the participants, this process will take considerably longer, maybe 10-15 minutes per story. Do the planning poker estimates, regardless, and plan on doing them again during a quicker second meeting. If you feel like you are bogging down on a story, and understanding of it is not "critical path," set it aside, and plan to come back to it after other stories are visited.
For a backlog of not-well-understood stories, you will probably want a couple sessions. Some stories will need to be set aside to split or researched offline. Some stories will need to be revisited by the customer. One of the best things to do is give people time to go off and think about things (and having at least one night between sessions is always a good idea).
Still, you want to avoid investing too much time in estimation. The more time you invest, the higher the expectation that the numbers coming out of it are anywhere near perfect. Estimates are guesses!
Instead, the estimation meeting is best seen as a way to ensure that we have good, appropriately sized stories that are fairly well understood by everyone involved. The consensus mechanism in planning poker will quickly let you know if this is not the case. Getting confidence from a good ballpark project plan is almost a bonus!







