Chapter 1 Estimating a login feature

How to estimate a login feature: the hidden scope — password reset, 2FA, federation, rate limiting, sessions — and the questions to land before anyone votes.

Chapter 2 Estimating an SSO integration

How to estimate an SSO integration: the work lives outside your codebase, in the identity provider's quirks. The questions to answer before you vote a number.

Chapter 3 Estimating a payment integration

How to estimate a payment integration: sandbox vs live, refunds, webhooks, idempotency, PCI scope. The conversation that has to happen before any number lands.

Chapter 4 Estimating a search feature

How to estimate a search feature: relevance, ranking, faceting and who owns the index. The questions that turn 'add a search bar' into a real estimate.

Chapter 5 Estimating a notifications system

How to estimate a notifications system: channels, preferences, deduplication and delivery guarantees. Why 'send an email' quietly becomes a six-week project.

Chapter 6 Estimating a file upload

How to estimate a file upload: size limits, virus scanning, resumability, storage and retention. The drag-and-drop is the easy part; underneath is the ticket.

Chapter 7 Estimating a dashboard

How to estimate a dashboard: data sources, refresh cadence, time zones, drill-down, permissions. The chart is easy; the data pipeline behind it is the work.

Chapter 8 Estimating a flaky test

How to estimate a flaky test: why it's two estimates, not one, and why a time-box beats arguing about points when the answer depends on what you find.

Chapter 9 Estimating a bug with no repro

How to estimate a bug with no repro: you can't size the fix, only the search. How to time-box the investigation instead of voting on a story nobody can see.

Chapter 10 Estimating a performance regression

How to estimate a performance regression: the work is mostly diagnosis, not the fix. How to size it when the cause is unknown and an SLO is on the line.

Chapter 11 Estimating a customer-reported bug

How to estimate a customer-reported bug: the account on the ticket decides the size. How to separate the one-line fix from the response that eats the sprint.

Chapter 12 Estimating a database migration

How to estimate a database migration: backfill, lock duration, rollout and rollback. 'Add a column' is one line of SQL; the estimate is about the second clock.

Chapter 13 Estimating a data migration

How to estimate a data migration: moving data between systems, reconciliation and cutover. The transform runs in an hour; the cleanup runs for a quarter.

Chapter 14 Estimating a framework upgrade

How to estimate a framework upgrade: why a major version bump is a project, not a ticket, and how to break it into stories you can actually size.

Chapter 15 Estimating a dependency upgrade

How to estimate a dependency upgrade: the long-tail bump that hides N spikes in one ticket. Read the changelogs first, then estimate what you found.

Chapter 16 Estimating a CI/CD overhaul

How to estimate a CI/CD overhaul: pipeline work has no demo, so slice by what can be deleted. The quarter-long story that hides on the backlog as a refactor.

Chapter 17 Estimating a third-party API swap

How to estimate a third-party API swap: semantic gaps, dual-running and the assumptions baked into the old vendor's quirks. The new API only looks identical.

Chapter 18 Estimating a rate-limit rollout

How to estimate a rate-limit rollout: thresholds, dry-run periods, customer comms. The code is half a day; picking limits nobody complains about is the work.

Chapter 19 Estimating a design-system change

How to estimate a design-system change: token rollouts, deprecation paths, codemod coverage and the 200 call-sites that use the old component. Size the downstream.

Chapter 20 Estimating an accessibility fix

How to estimate an accessibility fix: a11y issues are features you didn't ship the first time. Why to size the class of problem, not the single instance.

Chapter 21 Estimating a feature-flag rollout

How to estimate a feature-flag rollout: staged percentages, kill-switches, gating metrics and the cleanup nobody schedules. A flag is a small product, not a deploy.

Chapter 22 Estimating a research spike

How to estimate a research spike: a spike is a time-box with a deliverable, not a story. How to keep it from quietly becoming the work it was meant to scope.

Chapter 23 Estimating a prototype

How to estimate a prototype: it's a deliverable sized for learning, not for use. How to keep the throwaway from becoming the production code nobody planned for.

Chapter 24 Estimating an ML experiment

How to estimate an ML experiment: it's research with engineering attached — the model is easy, the data is the work. How to size a budget, not a forecast.