Estimation Roller Coaster


The estimation roller coaster can provide an unwelcome burst of adrenaline to an otherwise smoothly running project. Adapting estimates over time lets you plan and deliver value at a sustainable pace.

Estimating is hard. How do we do it right? Why do we have to do it, anyway? New agile teams can turn to excellent books, such as Mike Cohn’s Agile Estimating and Planning, to learn how to size user stories and estimate development and testing tasks. Estimates are often abused and treated as hard facts. Newbie teams underestimate, overcommit, and never achieve a sustainable pace. Do we even need estimates? Many teams do well with a lean or kanban approach, where work in process is limited and story estimates are unnecessary. 

My current team has ridden the estimating roller coaster for the past seven years. At times, we’ve become complacent, rolling along at a steady pace. Then suddenly, there’s an unexpected plunge into the unknown. I’d like to share our story of how we’ve adapted our sizing and estimating over time so that our business managers can track and plan and we can deliver value in a timely manner at a sustainable pace. 

Early Learning and Mistakes
Like many teams, we started with basic sizing and estimating practices. It seemed like we spent hours and hours in estimating meetings. We used Planning Poker, a consensus-based estimating technique, to size user stories, learning to compare user stories and assign relative story point estimates. Each person has a set of Planning Poker cards with these point values: 0, ½, 1, 3, 5, 8, 13, 20, 40, and 100. Our average two-point story takes two or three days to complete, including all testing activities. 

Here’s how we use our poker cards to size stories: After the product owner explains the story, we spend a few minutes discussing it and asking questions. Then, we count to three and each team member holds up a card. If we all hold up the same value, we’re done. If not, the people with outlying values explain why they chose them, and we estimate again until we agree on the size. We usually finish about fourteen story points in a sprint. Sometimes, we estimate a “theme,” which is a group of related user stories that provide a new feature. A theme estimate might be something like “20 to 40 points.” 

Sizing stories is tough early on, when your team doesn’t have much history to guide it. A story that we gave three points during our first year but that actually became a forty-point theme remains legendary (and cautionary!). Too often, we sized stories at a point value that was most of a sprint, learning the hard way to slice these into smaller increments. Still, our estimating process was good enough. When business development needed a new, complex feature in order to sign up a new partner, we could deliver it in a predictable timeframe. 

Complacency and Nasty Shocks
After a few years, we had boxes full of estimated story cards that were clearly never going to be prioritized. We studied the work of lean development experts, such as Mary and Tom Poppendieck, and started estimating only stories that would be done in the next two or three iterations. Through experimenting, we found we could best tackle complex new projects by starting with a few one-hour brainstorming and design meetings. We often map the theme on a whiteboard, showing workflow and interaction with the database and other parts of the system. We identify core system behavior and “nice to haves.” Then, we break the big theme into smaller stories and estimate them. If a story seems too large to be completed in two or three days, we break it up into smaller stories or “threads,” usually starting with the end-to-end happy path. We prioritized stories based on risk, dependencies, and importance. Fewer stories “blow up” and take way more time than we anticipated, so we’re able to maintain a steady pace. 

But software development is never certain. It seems that just as we are lulled into a sense of complacency, thinking we rock at estimating, our roller coaster track drops out from under us. Last summer, a five-point story that we thought we could finish in a week stretched into three two-week iterations. We hadn’t anticipated that its requirements necessitated a change in a basic model of our application, requiring not only code changes in other areas but also major database changes. The five-point size should have been a warning; when we get over three points on the Fibonacci-number scale, we enter risky territory. 

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