Gamblers Fallacy

There are eight people at this table. Four engineers, a product manager, a Scrum Master, a VP of Engineering, and a Director of Product who is visiting from the floor above and has brought her laptop, which she is not quite looking at. The calendar invite said "Sprint Planning" and blocked two hours. It is currently running at two hours forty minutes and nobody has acknowledged this.

On the screen at the front of the room there is a spreadsheet. The spreadsheet has a column called Velocity and a column called Points Remaining and a column called Sprints To Go and a column called Projected Completion. The Projected Completion column says October 14.

Nobody in this room believes October 14.

The VP of Engineering, whose name is James, has been looking at a slightly different version of this spreadsheet for six months. Every two weeks the Projected Completion date moves. Not dramatically — two days here, a week there, occasionally a fortnight when a sprint goes badly sideways. The date has moved, in aggregate, eleven weeks since the project started. James has learned to present the date in a tone that suggests it is stable. He has become, without intending to, an expert in the performance of confidence he does not feel.

The Director of Product, whose name is Miriam, knows the date is wrong. She has been in this industry for fourteen years. She has attended hundreds of sprint reviews. She has heard the date presented in exactly this tone — measured, considered, slightly defensive — at least forty times before. The date was wrong forty of those times. She is already doing the mental arithmetic for her own planning: take whatever James says and add eight weeks.

The engineers know the date is wrong. The one sitting closest to the door — her name is Fatima, she has been on the project since week one — privately believes the project is at least sixteen weeks from completion. She has not said this out loud because the last time she said something like it, in a retrospective three months ago, the conversation became uncomfortable in a way that took two weeks to fully dissipate.

The Scrum Master knows the date is probably wrong. He is twenty-six years old and this is his second job and he has not yet developed the vocabulary to say so in a way that will be heard rather than dismissed.

The product manager knows the date is wrong and has already sent a Slack message to a peer in another department that says, essentially, don't count on October 14.

Eight people in a room. Every one of them knows, to varying degrees and with varying specificity, that what is written on the screen does not correspond to reality. Nobody says so. The meeting continues. October 14 becomes the plan.

This is not a dysfunctional team. This is a normal team. This is every team. This is the planning meeting that happens every two weeks at thousands of companies across the industry, in slightly different rooms with slightly different spreadsheets and slightly different versions of James and Miriam and Fatima, all performing the same ritual of false certainty that everyone in the room recognises as false and nobody has the structural support to name.

Welcome to the casino.