Story Point Estimation Training Guide for Development Teams

Story points, simply put
Story points are a relative way to size work. They capture three things:
- Effort: How much work it will take
- Complexity: How tricky the problem is
- Risk/uncertainty: Unknowns that could slow us down
We compare work to other work instead of guessing hours. Humans are better at "bigger than / smaller than" than at "how many hours?"
Why points beat time
- Relative stays stable across people and calendars
- Embraces uncertainty instead of hiding it
- Drives healthy debate that surfaces assumptions
- Removes pressure to promise dates during sizing
The Fibonacci scale we’ll use
1, 2, 3, 5, 8, 13, 21. Bigger numbers jump more because bigger work carries more uncertainty. The point isn’t precision. It’s meaningful separation.
Calibrate your team’s scale
1) Pick reference stories
Choose a few known stories that feel like 2, 3, 5, 8, 13. These become anchors.
2) Define what each point means
A quick cheat-sheet your team can scan:
Points | What it feels like | Salesforce example |
---|---|---|
1 | Tiny, obvious, no risk | Update a field label or help text. Rename a picklist value used in UI only |
2 | Small, straightforward | Add a simple validation rule. Make a field required on a page layout. Add a dependent picklist value |
3 | Moderate with a few unknowns | Create a record-triggered Flow to auto-assign Cases and send an email with 1–2 decisions. Small Apex helper if needed |
5 | Multiple parts, clear path | Build a Screen Flow for Lead intake with duplicate check and assignment. Simple LWC to embed on a Lightning page |
8 | High complexity or risk | Integrate with an external service via Named Credential and Apex callouts, with retry and error handling. Update sharing and field-level security |
13 | Very large. Likely split | Refactor legacy triggers into a handler framework, migrate automations from Workflow Rules to Flow, and add a multi-step approval on Opportunity. Consider splitting by object or capability |
3) Recalibrate regularly
Review a few completed stories. Did the points match the feel in hindsight? Adjust anchors, not history.
Planning Poker, done right
Setup
- Everyone who helps deliver the story participates
- Make sure the story is understood
- Use Fibonacci cards or a simple app
Flow
- Present the story and answer quick questions
- Estimate silently
- Reveal together
- Discuss deltas: highest and lowest explain why
- Re-estimate until the group converges
When numbers diverge
That’s a gift. Ask what assumptions differ, which dependencies we missed, and what “done” means. Align on the shape of the work, then re-estimate.
Hands-on exercises
1) Comparative sizing wall
- Place stories left (smaller), right (larger), or under (similar) relative to a starting card
- Talk through moves
- When it settles, map groups to points
2) Bucket sort
- Set up buckets for 1, 2, 3, 5, 8, 13
- Drop each story into a bucket after quick debate
- Pick exemplar stories for each bucket
3) Paint the story point
- Teams estimate a simple creative task
- Do it, time it, compare to estimates
- Discuss what drove differences
Anti-patterns to avoid
- Converting points to hours: defeats the purpose
- Comparing velocities across teams: scales differ
- Expert-only sizing: you miss blind spots
- Changing estimates after delivery: keep history intact
- Using points as performance metrics: they’re for planning
Velocity, used well
Velocity is the average points finished per sprint.
- Track points for done stories only
- After 3–5 sprints, average them
- Plan using a range, not a single number
Notes:
- New teams need a few sprints to stabilize
- Expect variance; ranges are honest
Cross-team calibration (if needed)
- Bring 1–2 reps per team
- Estimate a shared set of 10–15 reference stories
- Publish the results and revisit quarterly
Rollout roadmap
Phase 1: Foundation (Weeks 1–2)
- Teach concepts and benefits
- Pick anchors and scale
- Practice Planning Poker on a slice of the backlog
Phase 2: Calibration (Weeks 3–6)
- Use points in sprint planning
- Compare reality to expectations in retro
- Refresh anchors as needed
Phase 3: Optimization (Weeks 7–12)
- Establish a stable velocity range
- Write lightweight team guidelines
- Tackle anti-patterns head-on
Phase 4: Mastery (ongoing)
- Keep refining through retros
- Calibrate cross-team when helpful
- Mentor new joiners on how we size
What makes this work
- Conversation over the number
- Uncertainty is part of the estimate
- Consistency beats precision
- Regular reflection improves accuracy
- Whole team participates
The goal isn’t perfect estimates. It’s shared understanding and better planning.
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