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Introducing Structured Story Points: A Practical Way to Estimate Engineering Work

· 4 min read
Mike Germain
Mike Germain
Engineering Leader

What are Structured Story Points?​

Structured Story Points (SSP) is a practical evolution of traditional story point estimation. It keeps what’s useful about story points but adds structure to make them actually usable in real-world planning. Instead of guessing a number or debating between a “3” and a “5,” SSP gives teams a shared way to evaluate work using four focused questions.

The method builds on the idea that engineering work is shaped by four key factors: effort, complexity, uncertainty, and collaboration. By scoring against each, teams can size stories quickly and consistently without losing the flexibility that makes story points useful in the first place.

The Four Key Questions​

1. Effort​

How much actual work will this take?
Effort refers to the hands-on time needed to complete the task. That includes coding, testing, documentation, and anything that takes focused execution.

  • Minimal – Can be completed quickly with little effort.
  • Moderate – Requires sustained focus over a day or two.
  • Painstaking – Involves a high level of effort or repetition over a longer period.

2. Complexity​

How difficult is the task to reason about?
Complexity is about how mentally or technically challenging the task is. It includes the number of moving parts and how much thinking it takes to do the work safely.

  • Simple – The work is easy to follow and unlikely to break anything.
  • Layered – Requires managing multiple concerns, systems, or logic paths.
  • Convoluted – Hard to understand or untangle without deep thought or review.

3. Uncertainty​

How well do we understand what’s being asked?
Uncertainty captures how much is still unknown. It helps teams flag when a story needs clarification or research before work can begin.

  • Clear – The task is well understood and scoped.
  • Murky – Some assumptions or open questions still need to be resolved.
  • Uncharted – We don’t know enough to start and need a research or discovery task first.

4. Collaboration​

Who needs to be involved to get this done?
Collaboration measures whether one person can complete the task alone or if it requires help from others inside or outside the company.

  • Solo – One person can complete the task independently.
  • Paired – Requires help from someone on your team.
  • Cross-team – Needs coordination with someone in another team.
  • External – Involves someone outside your organization.

Why Use Structured Story Points?​

I’ve used this method for nearly 15 years, and I keep coming back to it for one reason: it helps teams run clean sprints. Clean sprints build trust with stakeholders because they show consistent follow-through. That trust becomes the foundation for real collaboration and planning.

SSP also gives your team what it needs to own its work. When velocity is consistent, teams can advocate for more autonomy or clearly show when they need more support. Estimation stops being performative and starts being useful.

This method works because it is:

  • Fast – Estimation takes minutes, not meetings
  • Repeatable – Shared criteria make it easy to calibrate across a team
  • Transparent – Everyone knows what’s behind the number
  • Flexible – Works across product, platform, and devops teams

Try the SSP Calculator​

To make things even easier, I've built a tool that walks teams through each of the four questions and produces a score. Try it out on our Structured Story Points page.

Final Thoughts​

Story points aren’t broken. They just need more structure. Structured Story Points give teams a way to estimate collaboratively, quickly, and with clarity. It’s not about getting the number perfect. It’s about building shared understanding so you can plan and deliver with confidence.

Try it out and let us know how it works for your team.