When I first heard of estimating work items – let’s call them stories – with Story Points I was like “WOW!! That’s amazing!! No more question about how long it will take! Just estimating the relative effort, it really is a good idea!”

Then I discovered Planning Poker, and again was amazed by how it can solve Asshole Driven Development issues (me being the asshole most of the time). I immediately decided to apply it with the team I was in charge of. We did ONE session, and everybody agreed that we were wasting our time. Yet we learnt a couple of things then:

• We could easily treat small stories, the ones worth 1 or 2 points
• We could not easily decide about big stories, and almost always decided to break them into smaller stories

All around the Web you’ll see that people recommend not to use the bigger cards of your planning poker deck, and to only keep the 1/2, 1, 2, 3 ones or so.

So we decided to give a try to T-shirt-size estimates, which was basically like keeping only 3 cards in our deck : S, M and L. We did ONE session, and everybody agreed that we were wasting out time. Yet we learnt a couple of things then:

• We could easily treat small stories, the S-sized ones
• We could not easily decide about big stories, and almost always decided to break them into smaller stories

Now here is the thing : we had a product to build and we wanted to now how long it would take to build some of the pieces of it (we are not discussing why here). We realized that we could not give any (accurate) estimate to answer that very question unless the pieces were small enough.

So we decided to always work on small-enough pieces of work. Obvious.

Now if for some reason you believe that you need estimates, what you can try with your team, during your next Sprint Planning Meeting, is a session of Indian Planning Poker. You actually only need one card in your Planning Poker hand: the thumbs-up card. Stick the thumbs-up card on your forehead if the story is small enough, or as small as usual, and not if not…and tell me about the results.