In episode two of Brick By Brick, hosts Jeff and Mike delve into the challenges and strategies of estimating timelines for software development. Jeff shares his journey from frustration to discovering practical frameworks for scoping tasks and asking the right questions to avoid the common pitfalls of software estimation. The discussion highlights the paramount importance of clarity in understanding the problem, the customer, and ensuring alignment within the team. They introduce the concept of assessing tasks based on their complexity and uncertainty, offering a novel approach to estimate more accurately. The episode also emphasizes the necessity of explicit documentation and setting realistic expectations to mitigate the risks of timeline overextension, underscoring that clarity is the currency of execution. Through candid conversations and real-world anecdotes, the episode provides valuable insights for tech company builders on how to refine their software estimation processes.

Timestamps
00:00 The Philosophy of Opinionated Software
00:24 Introducing the problems with estimating software timeline
00:50 The Art of Estimating Software timelines
02:13 Unpacking the Challenges of Accurate Estimation
06:08 Frameworks for Better Estimation: Complexity and Uncertainty
11:53 Real-World Applications and Stories
19:40 Summing Up: Key Takeaways on Software Estimation
23:09 Looking Ahead: Future Episodes and Closing Thoughts

Connect with Mike:

Twitter / X

LinkedIn

SaaS Lead Flow

Connect with Jeff:

Twitter / X

LinkedIn

Jeff Builds Tech