Tolstoy on iterative development

But their mother country was too far off, and a man who has six or seven hundred miles to walk before reaching his destination must be able to put his final goal out of his mind and say to himself that he will 'do thirty miles today and then spend the night somewhere'; and during this first stage of the journey that resting-place for the night eclipses the image of his ultimate goal and absorbs all his hopes and desires.

- Leo Tolstoy, War and Peace

Fear-based estimation

I prefer agile development because early feedback mechanisms like TDD, pair-programming and frequent releases reduce my fear of the unknown. I don't like feeling afraid, but when I am I try to take notice, because it's usually an indication that something is not right.

A great agile tradition is acknowledging the human element in software development. In that spirit, I'd like to suggest that developers' fear can be harnessed to improve estimation.

Humans are notoriously bad at temporal reasoning and programmers are even-more-notoriously bad at guessing how long a given piece of work will take. Agile teams work around this by estimating effort in 'story points' that measure the comparative size of tasks. We might not be sure how long designing the new schema will take, but we assign it 2 story points because we know it will take twice as long as another task we gave 1 point.

The rate at which a team completes points is known as its 'velocity' and can be determined by examining the team's progress over time. It's a robust, self-correcting system, but I've observed two drawbacks on projects I've worked:

• The confidence of estimates isn't captured.
• The technical debt incurred by a particular piece of work is ignored altogether.

A story that has a chance of going horribly wrong and that will in any case cripple the system's architecture could receive a low story point score because it (probably) won't take long to implement. Confronted with such a story, developers are terrified - and helpless.

I propose that we estimate in terms of 'fear points' to give product owners a disincentive to prioritise dangerous stories. The question we ask in estimation meetings shouldn't be "how big is this task" but "how afraid does this task make you?".

So long as the developers have an appropriate level of professional cowardice, a story's fear points will reflect the danger the story represents to the project's current and future timelines. And I think that 'danger' is as useful to communicate to management as 'size'.

If product owners want to negotiate a reduction in a story's fear points then they need to reduce uncertainty, remove risky features and compromise on ideas that would incur a lot of technical debt. They could also prioritise other stories that improve the team's confidence in the development process, like improved Continuous Integration.

Whenever I have seen developers afraid of a feature, it turns out badly. It ends up buggy, expensive to change and probably doesn't serve its intended purpose. By gauging developers' fear, agile organisations have an opportunity to avoid trouble before it happens.

If your developers are afraid of a feature - be very afraid.