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Story Points vs Reality: What Estimation Really Shows

July 18, 2025

Maybe your story points and estimates are… pointless? 

This is the next step in our estimation series.

In the last post, we looked at how combining velocity with uncertainty can shift the conversation away from false certainty - Still Using Velocity? Make It Useful Again

Now we go a step further.

Because velocity alone isn’t the answer either. The real shift? Moving from estimation debates to data-driven predictability using flow metrics like cycle time and throughput to focus on value, not guesses.

Try This Simple Experiment

Here’s what we ask teams to do:

• Track the story point estimate for each Product Backlog item
• Track how long it actually took (cycle time)
• Plot them side by side

That’s it.

At first, it all seems to line up. A 2-point item takes 2 days. A 1-point item takes 1 day.
And then someone says the dreaded line, “A story point equals a day.”

It feels neat. Predictable. Like, maybe this whole estimation thing actually works.
And just like that, relative sizing slips back into absolute estimation.

But then you keep tracking. A 1-point item takes 6 days. A 5-point item finishes in 2 days. A 13-point item blows up completely.

The pattern breaks. And that’s when the lightbulb goes off.

You Can’t Beat Complexity with Precision

This isn’t about bad estimation.

This is about working in a complex space. Surprises happen. Dependencies emerge. Work changes shape as we learn.

You’re seeing the Cone of Uncertainty in action in the previous post, the idea that our ability to predict becomes less accurate the further out we look, especially when working with larger, more complex items.. The bigger the item, the greater the variation. The more unknowns, the more risk.

That’s why estimates fail when we try to use them to predict.

What the Data Shows

When teams run this experiment, a few things start to stand out:

• We’re working in a complex domain. Unknowns and surprises are normal
• Some large items turn out to be quick, while some small ones take much longer
• But teams often start to notice a pattern, a certain number just feels too big
• There’s no rule, but many teams see that items larger than 5 to 8 points often get messy, risky, and unpredictable
• That number is different for every team, but the pattern shows up again and again

It’s not about chasing precision. It’s about seeing complexity and using size as a signal, not a certainty

It’s Not About Points. It’s About the Conversation.

Story points, t-shirt sizes, and hours. Doesn’t matter. Estimation techniques are just tools to start the right kind of conversation:

• What are we building?
• What might trip us up?
• How confident are we?
• What’s the risk?

That’s the point. Not the number. Not the size. The shared understanding.

Of course, some estimation techniques can facilitate better conversations, but only if used correctly and with purpose.

Right-Size the Work

Once teams spot the pattern, they start letting go of point debates. They focus on breaking work down:

• Clear enough to talk about
• Valuable enough to deliver
• Small enough to finish in a Sprint or a few days

This is when estimation fades. Because once the work is the right size for the team, you don’t need to discuss further. You just get on with building it.

The team could do something as simple as a quick Roman vote, thumbs up or thumbs down, to decide if an item is small enough to bring into a Sprint. Or still using the Planning Poker technique to help make sure everyone feels the item is ready and the right size.

Either way, it’s not about the number - it’s about shared confidence. If not, the team asks: how can we break the item down into smaller & valuable deliverables?

From Estimation to Flow

Instead of trying to control complexity, teams begin to measure it. They start looking at:

• Cycle time
• Lead time
• Throughput

They use real delivery data to guide the next steps.

The result?

• Fewer debates
• Better predictability
• More value delivered

Not because they estimate better. But because they work better.

Help Teams See It for Themselves

This isn’t something to preach. It’s something to try.

Run the experiment. Share the data. Let the team reflect.

When they see it for themselves, the mindset shift sticks.

And estimation becomes what it was always meant to be, a conversation. Not a commitment.

Want to go deeper into flow-based forecasting?
Check out our next post: When Will It Be Done?, a hands-on guide for using flow data to forecast with real predictability.

If this series has caught your interest, we dig further in our training, particularly in Professional Scrum Master (PSM) and Professional Scrum Product Owner (PSPO), where we help teams shift the focus from output and estimation to the delivery of outcomes and value.

Want to explore this shift further? Check out Professional Scrum with Kanban (PSK). This course helps Scrum teams bring flow, data, and predictability into their way of working and value decisions.

Missed the earlier posts in this series?

Agile Estimation Is Not Broken. The Thinking Is.
Velocity. It’s Not What You Think It Is.
Still Using Velocity? Make It Useful Again

 


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