Rethinking Software Estimation

Who loves estimating how long it will take to deliver some features? The reason we don't like it is because we never have enough information. We have high level requirements with so many uncertainties that we have to make a lot of assumptions. We then pad our estimates with contingency to try to counter the inevitable misunderstandings, but this is frequently not enough.

But why do we estimate at all? Leadership need estimates to determine whether or not to fund a project. But we know that 90% of features fail to deliver the expected business value so the business case estimates and benefit projects are misleading.

A more effective approach is to shift the focus from project-based outputs to product-based outcomes. By measuring success through metrics like customer engagement and business impact, rather than effort or delivery timelines, teams can better align their work with organizational goals.

I go into more detail about how this works in my article listed below.

This Week’s Updates

Enabling the Team

When Extra Effort Makes You Worse At Your Job by Mouna El Mansouri, Karoline Strauss and Doris Fay
Putting in extra effort isn’t always productive, especially when it leads to burnout, resentment, or misaligned expectations. Knowing when to pull back can protect long-term performance and team health.

Happy Is Now Employee-Owned. Here's Why That Matters. By Happy Henry
Shifting to employee ownership can deepen engagement, trust, and a sense of shared purpose. When employees have a stake in outcomes, it changes how they show up, make decisions, and support each other.

Product Direction

Prioritization Techniques Compared by Iatmar Galad
Different prioritization frameworks produce very different results depending on how they're used. Comparing common methods like RICE, MoSCoW, and the Confidence Meter reveals trade-offs between simplicity, subjectivity, and strategic focus.

The 4 Framework Jobs (And Why It Matters) by John Cutler
Frameworks help teams make sense of complexity, but they serve different roles; sensemaking, aligning, deciding, and explaining. Knowing which job a framework is doing can prevent confusion and improve how teams communicate and act.

Continuous Research

Why We’re Taking Our Time With AI Moderator by Jonathan Widawski | Maze
Responsible AI design requires resisting the pressure to move fast and break things. Taking time for ethical reflection, cross-functional input, and iterative research leads to more thoughtful, inclusive outcomes. (Sponsored Article)

Synthetic Users: Is There A Place For “AI-generated Users” In Ux Research? by Daniel Mitev
AI-generated users promise faster insights, but they risk oversimplifying or distorting real human behaviour. The challenge is balancing speed and cost-efficiency with the depth and nuance of genuine user research.

Continuous Design

AI And Cognitive Offloading: Sharing The Thinking Process With Machines by Tetiana Sydorenko
By leveraging AI for tasks like data analysis and information retrieval, individuals can focus more on creative and strategic aspects of their work. This is  the concept of distributed cognition, where cognitive tasks are shared between humans and AI systems.

Less Effort, More Completion: The EAS Framework For Simplifying Forms by Huei-Hsin Wang
The EAS framework (Eliminate first, Automate where possible, and Simplify what remains) can help you minimize user effort and improve form completion rates.

Continuous Development

Rethinking Software Estimation From Outputs To Outcomes by Rory Madden
By shifting focus to outcomes, adopting product funding, and breaking stories into manageable, day-sized tasks, teams can plan more effectively and deliver higher-value software.

The Frontend Treadmill by Marco Rogers
Frontend development moves fast, but constant change doesn’t always mean progress. Staying intentional about what to adopt, and why, helps teams avoid wasteful churn and focus on delivering lasting value.

Did You Grab Your T-shirt At UXDX 2025?

Let’s dive into what this is all about…

At UXDX 2025, we had some memorable conversations sparked by our Pac-Man-style T-shirt. It got people talking and it encapsulates something we see time and time again: Strategy cannot exist in isolation.

If this resonates with you, we’re excited to invite you to our one-day, hands-on training in Barcelona on July 10, 2025. Led by Rory Madden, the training will dive deep into:

• Translating business goals into actionable product objectives

• Using KPIs to align teams and drive success

• Building product strategy that actually sticks

This workshop will equip you with the tools to drive product alignment and make your strategy more impactful. Plus, we’d love to see familiar faces join us for this focused, practical training.

Spots are limited, so secure yours today! Click here to book your ticket.

FREE COMMUNITY EVENTS 

Check out more upcoming community events 

Video of the Week
How to Choose the Right Tools for Product Development Teams

With countless tools available for product development, selecting the right ones can be overwhelming. In this session, Petra, Head of UXR at Omio, shares insights on how the right tools can streamline workflows and enhance product outcomes.

Learn how to make informed decisions when choosing tools for your team, and discover strategies for ensuring your tools align with your team’s needs. Watch now to get practical advice on optimizing your product development process with the right tools!

The Results of Last Week’s Poll

The question: Do you believe we should do smaller, more iterative releases?

This week’s poll results show a strong preference for smaller, more iterative releases in product development. 32% of respondents already implement this approach, while 14% believe their releases are too large and would benefit from more frequent, smaller updates.

Interestingly, 29% of teams opt for iterative releases when needed, reflecting a flexible approach to release planning. However, 16% don’t see the need for smaller releases, and 9% indicated that they face approval challenges when attempting to move to a more iterative model. These results suggest that while many teams recognize the value of smaller releases, organizational factors and approval processes still present bottlenecks for some.

If you’re looking to adopt more iterative release cycles or improve your release strategy, consider exploring approaches to streamline your development process in our Continuous Development course!

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