Estimations: a Love-Hate Affair
Let’s talk about estimations. No matter the project or task, someone will always ask, “How long will it take?” What seems like a straightforward question often turns into a rabbit hole of debates, disagreements, and dissatisfaction on every side.
If you’ve ever estimated a task to take “two weeks” only to see it extend out to a month, you’re not alone.
Estimations are not about strict timelines as the name already suggests. They should help in making valuable decisions, align the picture about what is planned and more.
In this guide, we’ll break down estimation methods, from Ideal Days to Story Points and #NoEstimates, so that by the end, you’ll not only know how to choose the right method but also why I prefer one over the others.
Why Do We Estimate?
Estimations are essential because they help teams and stakeholders make decisions. Stakeholders need clarity on timelines and costs to decide whether a project is worth pursuing. Teams need estimations to allocate resources, manage capacity, and prioritize work effectively.
However, estimations are not crystal balls. They’re educated guesses based on available information. Misusing them as guarantees often leads to disappointment. The key is to treat estimations as a tool for alignment and decision-making, not as promises that are carved in stone.
Challenges of Estimation
Estimations are difficult because of three key factors:
Uncertainty: Projects often involve unknowns, especially in the early stages when requirements are unclear (you can also check out the cone of uncertainty)
Complexity: The more moving parts a task or project has, the harder it becomes to predict effort accurately.
Human Nature: People are naturally bad at predicting time, particularly for unfamiliar or complex tasks.
These challenges highlight the importance of choosing an estimation method that matches the complexity and uncertainty of your work.
Matching Estimation Methods to Complexity
Different estimation methods are suited to different types of work. I will "misuse" the Stacey Matrix to determine which method fits best:
Simple work (low unclarity, low uncertainty): Ideal Days.
Complicated work (medium unclarity, low-medium uncertainty): Story Points.
Complex work (medium-high unclarity, medium-high uncertainty): #NoEstimates.
Let’s break down each of these methods to understand how they work, when to use them, and how to avoid common pitfalls.
1. Ideal Days: Best for Simple Work
What Are Ideal Days?
Ideal Days represent how long a task would take if completed without any interruptions or distractions. For example, writing a report might take two Ideal Days if you worked on it with perfect focus and no interruptions.
This method assumes an ideal world, which is its greatest strength and its biggest weakness.
When to Use Ideal Days
Ideal Days are best suited for simple, predictable tasks with low uncertainty. Routine maintenance, repetitive updates, or straightforward administrative tasks are great candidates for this method.
Tips for Using Ideal Days
Break Tasks into Smaller Pieces: Divide larger projects into manageable tasks to avoid underestimating complexity.
Factor in Real-World Conditions: Adjust estimates to account for interruptions, meetings, and collaboration.
Be Clear About Assumptions: Communicate that Ideal Days assume perfect working conditions.
Pros and Cons of Ideal Days
Pros:
Simple and easy for everyone to understand.
Effective for routine, predictable work.
Cons:
Unrealistic for complex or collaborative tasks.
Does not account for interruptions or dependencies.
2. Story Points: A Flexible Agile Favorite
What Are Story Points?
Story Points measure the relative effort, complexity, and risk of a task. They’re not tied directly to time but instead focus on comparing tasks to each other. For example, a login page might be a 3, while a payment gateway could be an 8 because it’s more complex and time-consuming.
Story Points encourage teams to think in terms of effort rather than hours or days, which helps reduce the pressure of creating precise predictions.
When to Use Story Points
Story Points are ideal for tasks with medium unclearity and low uncertainty. They work well for Agile teams operating in sprints or iterations, where tasks can be broken down and prioritized collaboratively.
Understanding Variability in Story Points
Story Points are not precise measurements, which is intentional. A task estimated at 5 points might sometimes take the same time as a 3-point task or an 8-point task, depending on factors like unexpected challenges or team capacity.
This variability highlights the importance of treating Story Points as guides, not guarantees.
Tips for Using Story Points
Anchor Your Scale: Use a familiar task as a baseline to compare others against.
Involve the Team: Collaborative techniques like Planning Poker, Wall of Estimation etc. help ensure alignment.
Focus on Relative Effort: Comparisons over precision, and avoid tying Story Points to time.
Pros and Cons of Story Points
Pros:
Encourages team collaboration and alignment.
Scales well for Agile workflows and iterative projects.
Cons:
Often misunderstood as direct time estimates.
Requires consistent calibration within the team.
3. #NoEstimates: Embrace the Unknown
What Is #NoEstimates?
#NoEstimates challenges the idea that traditional estimation is necessary. Instead of guessing how long tasks will take, it focuses on delivering small, valuable increments of work and using historical data to forecast timelines.
The goal is to reduce time spent on estimation and increase time spent on value creation.
When to Use #NoEstimates
This method is most effective for medium-to-high-uncertainty, medium-to-high-complexity projects where traditional estimation methods struggle.
It works particularly well for teams with established metrics and a focus on continuous value delivery.
Tips for Using #NoEstimates
Track Throughput: Monitor how many tasks your team completes in a given period to forecast future performance.
Deliver Incrementally: Break down work into small, meaningful chunks that can be delivered quickly.
Educate Stakeholders: Explain why this approach focuses on outcomes rather than predictions.
Pros and Cons of #NoEstimates
Pros:
Saves time by eliminating lengthy estimation discussions.
Focuses on delivering value rather than debating timelines.
Cons:
Requires trust from stakeholders who may be accustomed to traditional estimates.
Depends on reliable historical data, which new teams may lack.
My Preferred Approach
I’m a bit of a #NoEstimates fan. There’s something freeing about skipping the debates and focusing on delivering value.
However, I recognize that there are times when stakeholders need a sense of effort to make decisions. In those cases, I lean toward Story Points.
They encourage meaningful conversations, align teams, and allow for flexibility, making them a reliable fallback.
Ideal Days? They’re fine for simple, predictable work, but in my experience, they fall apart as soon as the complexity increases.
Conclusion: Deliver Value, Not Predictions
Estimations are not about being perfect but about being practical.
Whether you use Ideal Days, Story Points, or #NoEstimates, the goal remains the same: align teams, manage complexity, and deliver value effectively.
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