
Co-Founder of Momentum. Formerly Product @ Klaviyo, Zaius (acquired by Optimizely), and Upscribe.
Table of Contents
- Stop Guessing How Long Work Will Take
- Embracing Relative Sizing Over False Precision
- Why This Shift Matters
- Why Points Beat Hours Every Single Time
- The Magic of Relative Sizing
- Comparing Story Points vs Time-Based Estimates
- From Wild Guesses to Predictable Sprints
- How to Run an Estimation Session That Actually Works
- The Planning Poker Ceremony
- Turning Disagreement into Discovery
- Common Pitfalls and How to Sidestep Them
- Maintaining Estimation Sanity
- Practical Ways to Stay on Track
- From Abstract Points to Concrete Plans
- A Few Lingering Questions...
- "Great, But My Boss Wants Estimates In Hours."
- "How Do We Estimate The First Stories With Zero History?"
- "Do We Really Need to Put Points On Bugs and Chores?"

Do not index
Do not index
Let's be honest. You ask an engineer how long a task will take, they toss out a number in hours, and you both silently agree it’s a complete shot in the dark. That estimate sounds precise, but it's pure fantasy.
The moment some gnarly, unexpected bug crawls out of the woodwork or a requirement gets slightly misinterpreted, that neat little 8-hour task bloats into a 20-hour saga. Boom. Your timeline is shot, your credibility takes a hit, and the whole miserable cycle of missed deadlines starts all over again.
This isn’t a sign of bad engineers. It’s a sign that you’re asking the wrong question.
Stop Guessing How Long Work Will Take

There’s a better way, and it’s called user story point estimation.
Embracing Relative Sizing Over False Precision
This whole approach isn’t about finding some secret formula to convert points back into hours—that defeats the entire purpose. It's a fundamental mind shift. You move away from the false comfort of time-based estimates and toward a shared, relative understanding of the work itself.
Think of it like this. When you estimate a story, you're really weighing a few key ingredients together:
- Complexity: How thorny is this problem? Is the logic straightforward or a tangled mess of spaghetti code?
- Risk & Uncertainty: What are the big unknowns? Are we dealing with a shaky third-party API or a part of the codebase no one has dared touch in years?
- Repetition: Is this a task the team has done a dozen times before, or are we venturing into brand new, uncharted territory?
By bundling these factors into a single, abstract number, you stop obsessing over the clock. Instead, you start having much more productive conversations about what it will actually take to get something done. This isn't a new fad; it's a concept that has been battle-tested for decades to give agile teams a more reliable way to gauge effort. You can learn more about the origins of user story points on easyagile.com.
Why This Shift Matters
Here’s where the magic happens: this method removes the individual from the equation. A senior engineer might blaze through a task in half the time it takes a junior engineer, but the inherent difficulty of that task doesn't change. Story points capture that constant.
Story points are a team’s agreement on the overall size of a story, independent of who does the work. It’s about the “what,” not the “who” or the “how long.”
This abstraction is liberating. It forces your team to align because everyone has to discuss the actual work, not just how fast they personally code. It drags hidden assumptions and unspoken fears out into the light and sparks critical conversations before a single line of code is written.
Let’s break down exactly why this works and how it can finally stop your team from being slaves to the clock.
Why Points Beat Hours Every Single Time

Let's be real, estimating in hours is a recipe for misery. It’s a game everyone knows is rigged from the start.
A senior engineer might blast through a task in 4 hours. That same task could take a junior developer a full 12 hours, maybe more. So, what's the "real" estimate? Is it a 4-hour task or a 12-hour one?
It's a trick question. The answer is neither. The work itself has an intrinsic size, no matter who's doing it.
This is exactly where user story point estimation comes in and saves the day. It pulls the focus away from the individual and puts it squarely on the work.
The Magic of Relative Sizing
Think about it like moving furniture. Shifting an office chair is easy—let's call it a 1-point task. Now, imagine hauling a massive three-seater couch up a spiral staircase. That’s a whole different beast—maybe a 5-point task.
It doesn’t matter if you have a professional weightlifter or a scrawny intern doing the moving. The couch is just fundamentally harder to move than the chair.
By focusing on relative effort—which includes complexity, risk, and just plain repetition—you build a stable, team-wide language for talking about work. It’s a language that goes beyond individual skill levels.
This shared understanding is a game-changer. A senior and a junior dev can both look at a user story and agree, "Yep, that feels like a 5," even if their personal time to finish it would be wildly different.
They're agreeing on the size of the mountain, not arguing about how fast each of them can climb it. If you want to dig deeper into what’s truly worth tracking, this software development metrics guide is a great place to start.
Comparing Story Points vs Time-Based Estimates
To really see the difference, it helps to put them side-by-side. One is about abstract effort; the other is a slave to the clock.
Factor | Story Point Estimation | Time-Based Estimation (Hours) |
Focus | Relative effort, complexity, and risk | Concrete time to complete a task |
Unit | Abstract points (e.g., Fibonacci sequence) | Hours, days, or other time units |
Perspective | Team-centric and collaborative | Individual-centric and skill-dependent |
Consistency | Stable over time, regardless of who does the work | Varies wildly between team members |
Impact of Interruptions | Absorbs unknowns; estimate remains valid | Immediately makes the estimate inaccurate |
Psychology | Fosters discussion about "how big" | Creates pressure and commitment to a deadline |
The takeaway is clear: points encourage a conversation about the problem, while hours force a premature commitment to a solution's timeline.
From Wild Guesses to Predictable Sprints
This consistency is what unlocks predictability. Your team's velocity—the number of points they knock out each sprint—becomes a reliable gauge of what they can actually handle. No more wishful thinking or heroic commitments doomed to fail.
This isn't just some agile theory, either. Data shows that around 70% of software teams have switched to story points, and for good reason. They see a 25-30% improvement in sprint predictability compared to teams sticking with time-based estimates.
Teams using points just get more of their committed work done. Why? Because the estimate itself already has the messy realities of development—the unexpected bugs, the surprise meetings, the inevitable context switching—baked right in.
Of course, this only works if your estimates are based on well-defined tasks. Make sure your team has a solid foundation by checking out our guide on how to write good user stories.
Ultimately, points win because they force the right conversations. Instead of getting bogged down debating who is faster, your team starts talking about the real challenges and unknowns in the work. That shared understanding is what makes for a successful sprint, long before a single line of code is written.
How to Run an Estimation Session That Actually Works
Theory is great, but putting it into practice without creating yet another soul-crushing, useless meeting is the real trick. Pulling this off boils down to two things: structure and collaboration. You need a process that doesn't just ask for a number but forces a real conversation.
The most popular—and frankly, most effective—technique for this is Planning Poker. It’s not as nerdy as it sounds. Okay, maybe it is, but it works.
Here’s how to run a session that generates actual insights, not just a spreadsheet full of empty numbers.

This whole process is a loop—from introducing the story to hammering out a shared understanding and finally landing on an estimate everyone can stand behind.
The Planning Poker Ceremony
The product manager kicks things off by presenting a single user story. The goal here isn't to solution the entire feature on the spot. Instead, the team’s only job is to ask just enough clarifying questions to wrap their heads around the "what" and the "why."
Once everyone feels like they get it, it’s time to vote.
- Private Estimation: Each team member privately picks a card that represents their estimate. Most teams use a modified Fibonacci sequence (0, 1, 2, 3, 5, 8, 13...). That non-linear scale is intentional; it’s a built-in reminder that the gap between a 1 and a 2 is tiny compared to the chasm between an 8 and a 13.
- The Reveal: On the count of three, everyone flips their card over at the same time. This simultaneous reveal is the secret sauce. It prevents the "anchoring" effect, where the first number someone throws out silently influences everyone else’s guess.
If the numbers are pretty close—say, a mix of 2s and 3s—you can usually just take the higher number, log it, and move on. The real magic happens when the numbers are all over the place.
Turning Disagreement into Discovery
What happens if one engineer holds up a '2' and another flashes an '8'? Don't panic. This isn't a problem; it’s the entire point of the exercise. A wide spread just means someone knows something the rest of the team doesn't.
A large gap in estimates isn't a sign of conflict. It's an invitation to a conversation that will uncover hidden complexities, risks, or assumptions before a single line of code is ever written.
This is where the high and low estimators explain their thinking. The '2' estimator might say, "Oh, we have a library that handles this entire workflow, so it's just a simple integration." But the '8' estimator might fire back, "I was in that library last month, and it doesn’t support the new authentication method this feature needs. We’ll have to rewrite a huge chunk of it."
Boom. Just like that, you’ve uncovered a massive dependency that would have blindsided the team halfway through the sprint. This is exactly what happened at a SaaS startup I worked with; a simple-looking feature became a month-long refactor because one quiet engineer finally spoke up during poker, saving us from a commitment we could never have met.
This is exactly why teams switched to points in the first place. Back in 2015, a case study with a multinational bank showed that adopting story points helped their team improve delivery time by about 15% simply by exposing these hidden hurdles early on.
After the discussion, you vote again. Almost every time, the numbers converge as the team reaches a shared understanding. This isn’t about arguing until someone gives in. It’s about sharing knowledge to create a more accurate, collective picture of the work.
If you want to explore this and other techniques, we've got a deep dive on agile estimation methods that goes even further.
Common Pitfalls and How to Sidestep Them
Adopting story points isn't a magic bullet—you can still mess it up spectacularly. There are a few classic traps that teams fall into, but with a little foresight, you can sidestep them completely.
The number one mistake is trying to translate points back into hours. I can’t tell you how many times I've heard a well-meaning manager say, "Okay, so for our team, one point equals four hours." Don't. Do. It. This immediately destroys the value of relative estimation and drags you right back into the time-based misery you were trying to escape.
Another classic trap is letting a single person, like a tech lead or senior engineer, dictate the points. Estimation is a team sport. The real value comes from the collective wisdom—and the crucial conversations that happen when different perspectives clash.
Maintaining Estimation Sanity
To keep your process healthy, you need to watch out for a few specific anti-patterns. These issues can creep in slowly and completely erode the trust your team has in the system.
- Point Inflation: This is when a story that would have been a 3-pointer last quarter suddenly becomes a 5-pointer today. It happens when teams lose their frame of reference.
- Velocity as a Weapon: Using velocity to compare teams is a cardinal sin. Team A's 20 points is not inherently better or worse than Team B's 40 points. Their scales are completely different.
- The Lone Estimator: When one person dominates the conversation, you lose the most important benefit of the process—uncovering hidden complexities through shared dialogue and disagreement.
Each team's point scale is unique to them, like a local dialect. Comparing velocity between two teams is like arguing whether a kilometer is "better" than a mile. They're just different units of measurement for different contexts.
Practical Ways to Stay on Track
So, how do you keep these problems from taking root? It’s all about creating guardrails and shared reference points.
A simple but powerful technique is to establish a few "golden standard" stories. Pick a few well-understood, already-completed stories that the team agrees on. For example, "Remember that login button feature? That's our benchmark for a 2-point story. And the user profile redesign? That's what a classic 5-pointer looks like."
When point inflation starts to happen or scope creep begins to muddy the waters, you can pull out these reference stories to recalibrate. Speaking of which, it's crucial to understand how to handle scope creep as it can easily derail your estimations and sprint goals.
By avoiding these pitfalls, you protect the integrity of your user story point estimation process. It becomes a reliable tool for forecasting and planning, not just another number to argue about in a meeting.
Alright, you've got a backlog filled with freshly estimated stories. Now what? This is where the magic happens—where all that collaborative pointing and debating finally translates into a predictable, sustainable rhythm for your team.
When you sit down for sprint planning, you're no longer just grabbing a random handful of tasks that feel like the right amount of work. Instead, you're making a commitment based on a specific number of story points. And that commitment isn't based on a gut feeling; it's grounded in cold, hard data: your team's historical velocity.
From Abstract Points to Concrete Plans
So, what's velocity? It's just the average number of story points your team actually completes in a sprint. Forget wrangling spreadsheets—modern project management tools can track this for you, taking all the guesswork out of the equation.
This little chart tells a powerful story. It shows your team's true capacity, in black and white. You can see, sprint after sprint, exactly what your team can realistically get done. No more wishful thinking.
This is the insight that lets you make commitments you can actually keep. If your team's average velocity is 25 points, you know that pulling 40 points into a sprint isn't just "being ambitious." It's a one-way ticket to burnout and missed deadlines. Having this data right in front of you turns sprint planning into a realistic, data-informed conversation.
The real goal of story points isn't just to put a number on a task. It's to create a predictable heartbeat for the team. Velocity is that heartbeat.
Of course, once you have these estimates, you need a place to put them. To keep things moving, you'll want to explore how to effectively integrate estimations into your task management. This is the crucial step that turns those abstract numbers into a real plan for shipping great work.
This whole process is a cornerstone of a healthy workflow. If you want to see how this fits into the bigger picture of running a software team, check out our complete guide on project management for software development. By grounding your plans in real data, you transform your story points from a guessing game into a reliable engine for building momentum.
A Few Lingering Questions...
Even with the best intentions, a few predictable hurdles always pop up when a team first dives into story points. Let’s get ahead of them now so you can sidestep the drama and handle any pushback like a pro.
"Great, But My Boss Wants Estimates In Hours."
This is the classic standoff. It's totally understandable—your leadership team isn't trying to be difficult; they're trying to forecast, budget, and make promises to the business. The trick is to reframe the conversation.
Instead of trying to create some wonky hours-to-points conversion chart (don't do it!), use your team's velocity to give them the predictability they crave.
Try this: "Our team's average velocity is 30 points per two-week sprint. This epic is sitting at 120 points, so we're forecasting it'll take about four sprints, or eight weeks, to wrap up."
You're giving them the timeline they need for their spreadsheets, but you're doing it on your terms. This protects the team from the death march of hourly estimates. You've answered their real question—"When will it be done?"—without derailing your entire process. This shift is a core part of what makes agile different from rigid, old-school waterfall methods, which you can read more about in our deep dive on the difference between agile and waterfall.
"How Do We Estimate The First Stories With Zero History?"
Look, your first estimation session is going to feel like you're throwing darts in the dark. That’s fine. The goal isn't perfection; it's to create a single point of reference.
Comb through your backlog and find one small, dead-simple story that everyone on the team understands completely. This little story is now your North Star—your benchmark. Call it a 1 or a 2-point story.
From that moment on, every other estimate is just a comparison. "Is this new story harder than our benchmark? Is it about twice as complex? Three times?"
Your first few sprints will feel a bit wobbly, and that's okay. The magic happens after a couple of cycles when the team starts to build a shared gut feeling for what a "5-point story" really means.
"Do We Really Need to Put Points On Bugs and Chores?"
Ah, the great debate. There are two main camps on this, and honestly, neither is a silver bullet.
- Point Everything That Moves: Some teams slap points on every last thing—features, bugs, chores, you name it. This gives them a crystal-clear picture of exactly where all their effort is going.
- Protect Your Capacity: Other teams only point new, shiny, value-adding user stories. Then, they fence off a percentage of their sprint capacity (say, 20%) just for dealing with bugs and other housekeeping tasks.
The second approach is usually simpler. Trying to estimate the "complexity" of a bug that no one understands yet can turn into a philosophical debate that drains the will to live.
My advice? Pick one and try it. If it’s creating more arguments than clarity after a few sprints, ditch it and try the other way. The most important thing is to be consistent.
Ready to stop juggling a dozen different tools and give your team one place for planning, tracking, and shipping? Momentum brings your entire agile workflow—from standups to sprint planning—into a single, unified platform. See how a two-way Jira sync and built-in story pointing can finally get your process running smoothly. Try it free.
Written by

Avi Siegel
Co-Founder of Momentum. Formerly Product @ Klaviyo, Zaius (acquired by Optimizely), and Upscribe.