1,000 Projects Later: How to Approach Estimation Like a Pro

Estimation is a fundamental skill in software development, yet it's a topic that often gets little attention. Whether you're scoping out a complex system, designing a new app feature, or planning a personal project, the process involves more than just guessing how many hours it will take. It requires asking the right questions, understanding the bigger picture, and navigating ambiguity with a clear strategy.

This talk draws on years of experience evaluating projects and focuses on actionable insights for turning loose ideas into structured plans. It’s not just about numbers—it’s about cultivating the right mindset to build strong teams, establish sound architectures, and set projects on a path to success. And no, scrum poker isn’t on the agenda.

Key topics include:

• The importance of understanding the business context—regardless of your role.
• Why hypotheses matter more than hours—and how to formulate them effectively without getting bogged down.
• Strategies for breaking down tasks into manageable components for better accuracy.
• How to account for risks—and the cost of overlooking them.
• Communication do’s and don’ts—why knowing your audience matters, and when “just ask questions” might not be the best advice.

This session is designed for anyone involved in software development, from junior engineers to seasoned architects. It’s a practical, straightforward look at a skill we all use but rarely examine, offering tools and perspectives to approach estimation with confidence and clarity.