Why Agile Estimation Fails (and What You’re Really Measuring)
Published:
Part 1 of the “Why Agile Metrics Can Be Misleading” Series
Chasing Speed: The False Promise of Agile Metrics
Agile was supposed to be a game-changer. It promised speed, flexibility, and a laser focus on customer value. Teams worldwide embraced its principles, hoping to deliver better software faster. But somewhere along the way, many teams lost the plot.
Instead of focusing on customer value, they began chasing numbers—velocity, story points, and burndown charts. Metrics meant to provide insights became the goal in themselves. Developers found themselves estimating endlessly, discussing the difference between a “3-point story” and a “5-point story” as if their careers depended on it.
We’ve seen it firsthand. Teams huddled around virtual whiteboards, arguing about whether a task is a 2-point or a 3-point story, as if this would make them faster. Product owners pressuring teams to increase their velocity, not realising that this was leading to inflated estimates and rushed work. Managers proudly reporting on “improved velocity” without noticing that quality was quietly falling apart.
But there’s a problem—these metrics can be deceiving. A team can look incredibly productive on paper—burning through points, closing tickets—while actual customer value remains stagnant.
The truth is, most of these metrics measure the wrong things. They reward teams for staying busy, not for solving real problems. They encourage teams to focus on effort, not impact.
But it doesn’t have to be this way.
In this series, we’ll take a hard look at the dark side of traditional Agile metrics, starting with one of the most persistent problems—estimation.
The Estimation Trap: Why Agile Gets It Wrong
We’ve all been there: a planning session that spirals into a debate over whether a task is a three-point or a five-point story. These discussions, while seemingly productive, often mask a deeper issue—our reliance on estimation as a cornerstone of Agile planning.
The Illusion of Precision
Estimations are inherently uncertain. As Mike Cohn aptly puts it, “To be uncertain is to be uncomfortable, but to be certain is to be ridiculous.” Yet, in many Agile environments, there’s an unspoken expectation that estimates should be accurate, leading teams to spend excessive time refining them.
But let’s be honest—most of these estimates are little more than educated guesses. Research shows that even experienced teams can be wildly inaccurate in their estimates, with a 2021 study revealing that variance between individual estimates can exceed 300% (arxiv.org). Despite this, teams continue to treat these estimates as commitments, rather than the rough predictions they were meant to be.
Subjectivity and Variability
Story points, designed to measure relative effort or complexity, often become a source of confusion. What one developer considers a two-point task, another might view as a five-point challenge. This subjectivity undermines the consistency of estimates, turning planning sessions into debates rather than decisions.
We’ve seen teams where senior developers dominate estimation discussions, their experience intimidating less experienced members into accepting their estimates without question. This disagreement can also sow mistrust amongst the team if individuals start to doubt the capability of their colleagues. In other cases, teams spend time debating the difference between “complexity” and “effort,” losing sight of the real goal—solving problems for users.
Pressure and Misaligned Incentives
The emphasis on meeting estimates can create undue pressure. Teams often feel compelled to complete their planned points, regardless of the actual value those points deliver. This is particularly true in organisations where velocity is treated as a measure of productivity.
In these environments, developers may inflate estimates to ensure they hit their targets. Worse still, they may rush their work to complete as many points as possible. This leads to a vicious cycle of technical debt, with shortcuts taken today becoming bugs tomorrow.
Focus on Effort Over Value
Perhaps the most significant flaw in traditional estimation is the shift in focus from delivering customer value to completing estimated tasks. When success is measured by the number of story points completed, teams may prioritise quantity over quality.
We’ve seen this happen in real teams—where product owners push for high-velocity sprints, only to find that the features delivered are half-baked, buggy, or misaligned with user needs. In these cases, the obsession with completing points has overshadowed the real goal of Agile—delivering working software that solves real problems.
In recognising these pitfalls, it is clear that traditional estimation methods can lead teams astray. By acknowledging the limitations of these practices, we can begin to explore more effective ways to plan and deliver value in Agile environments.
Estimation Overload: The Productivity Sink No One Talks About
Ask any Agile team about their busiest days, and you might expect to hear about release deadlines or complex bug fixes. But in our experience, some of the most draining days aren’t spent writing code—they’re spent estimating.
We’ve seen teams burn hours—sometimes entire days—huddled in planning sessions, debating the difference between a two-point task and a three-point task. What starts as a discussion about work often turns into a debate about semantics. Developers argue over complexity, product owners try to quantify uncertainty, and managers sit quietly, hoping the final number will offer predictability.
But this obsessive focus on estimation is a productivity trap. It turns planning into an endless cycle of guesswork and rework, stealing time that could be better spent building and delivering value.
Planning Poker: A Well-Intentioned Distraction
Many teams rely on techniques like Planning Poker—a method where team members use numbered cards to “vote” on the estimated size of a task. In theory, this creates consensus. In practice, it often leads to endless discussions.
- “But is it really a three? I think it’s a five because it’s more complex.”
- “Sure, but if we break it down, it might be a two.”
- “Maybe we should just go with a four to be safe.”
Instead of clarity, teams are left with confusion, and a simple decision becomes a debate.
A study by QSM Associates found that the most accurate estimates come not from detailed planning, but from historical data on team throughput—how much work they have actually completed over time (QSM Associates). This aligns with our own experience—teams that focus on delivery, rather than estimation, are often the most consistent.
Constant Re-Estimation: Chasing Accuracy, Losing Time
Even when teams do settle on estimates, the obsession doesn’t end. As work progresses, teams often feel compelled to re-estimate tasks:
- A ticket initially estimated at three points becomes a five-point task when unexpected complexity arises.
- The solution for a task requires deeper discovery, resulting in an additional spike that needs time-boxing.
- A simple bug fix turns into a multi-step refactor, prompting a mid-sprint discussion on how to “re-estimate” the story.
- Product owners demand new estimates for work that has been reprioritised mid-sprint.
This constant re-estimation is not just a waste of time—it’s a signal that the team’s focus has shifted from solving problems to justifying estimates.
Estimation as a False Measure of Productivity
Perhaps the most damaging effect of estimation overload is when estimates become a proxy for productivity. Teams that complete more points are seen as more productive, even if those points are inflated or represent low-value work.
We once worked with a team where managers measured team performance by the velocity of points completed. Within months, developers began inflating estimates to maintain a steady velocity, while bugs piled up in production. The team looked “productive” on paper, but user satisfaction plummeted.
This is not an isolated case. A 2020 survey by the Project Management Institute found that 43% of Agile teams reported significant pressure to maintain or increase velocity, even at the expense of quality (PMI Pulse of the Profession).
The Cost of Estimation Overload
- Lost Development Time: Hours spent debating estimates are hours not spent building solutions.
- Decision Fatigue: Teams become drained by constant discussions, making it harder to make meaningful decisions.
- Distracted Focus: Instead of solving customer problems, teams become focused on meeting point targets.
- Degraded Quality: Rushed work leads to shortcuts, technical debt, and lower code quality.
It’s time to stop confusing estimation with value. The most effective Agile teams we’ve worked with are those that focus on delivering real outcomes, not on perfecting their estimates.
Conclusion
Estimation is supposed to make Agile teams more predictable. But in reality, it often does the opposite—wasting time, creating pressure, and shifting focus from value to vanity metrics.
If your team spends more time debating estimates than delivering value, you’re not alone. But there is a better way.
Coming Up Next
In Part 2: The Problem with PI Planning and the Truth About Agile Metrics, we’ll explore how attempts to create perfectly predictable plans can lead teams astray, why standardised estimates are a waste of time, and how traditional metrics like velocity and story points can drive the wrong behaviours.
About the Author
Tim Huegdon is the founder of Wyrd Technology, a consultancy specialising in helping teams achieve operational excellence through pragmatic, value-driven Agile practices. With extensive experience in software engineering leadership, Tim has guided teams across multiple industries to break free from misleading metrics and focus on what truly matters—delivering value.