I Hope You Fail

How obsession with tactical success prevents strategic success.

“Matt, sometimes I doubt your commitment to Sparkle Motion…” Of course my scrum master didn’t actually reference Donnie Darko, it was just my brain coping at the absurdity of it all. My team had failed. We had missed our sprint commitments again, and he was pissed off. This was the third or fourth conversation we’d had and they were pretty similar. The scrum master would explain to me the importance of following The Plan and I would explain that I didn’t give two shits about his Plan.

His solution it seemed was to sell me again on The Plan, only louder. After a bit of polite listening I decided to take a different tact, “look, what you are asking for is for my team to tell the future. How long is this work going to take? That is never going to be 100% accurate. Just how much certainty do you want in our estimates?” He took a moment wondering if this was some sort of trap. (It was.)

“Ninety-five percent? Cool, a one in twenty chance to be wrong. Optimistic, but let’s go with it. How many user stories do we pick up a sprint? Ten? Let’s assume ten to make the math easy. The problem is now that we take that one in twenty chance ten times, meaning (quick math) my team will miss their estimates about forty percent of sprints. Even if you think that engineers will estimate high as often as they estimate low (hah!), that’s still about one in five sprints we’ll overestimate — best case.” The scrum master considered it, and we didn’t…