Max Guernsey, III, Co-Author of Ready: Why Most Software Projects Fail and How to Fix It

In this Leanpub Podcast episode, Leanpub co-founder Len Epp interviews Max Guernsey, III, co-author of Ready: Why Most Software Projects Fail and How to Fix It and co-founder of Producore.

With nearly 30 years in the software industry, Max shares insights from his diverse career across technologies and domains. He discusses why so many software projects fail - often due to the gap between strategy and execution - and how organizations can address these problems through better alignment and learning.

The conversation explores Max’s work in consulting, his perspective on Agile practices, and his emphasis on creating the conditions for teams to succeed. He highlights how focusing on readiness, rather than rushing to execution, can dramatically improve outcomes. Along the way, Max shares practical advice on building healthier organizations, fostering adaptive learning, and making Agile principles work in practice rather than in theory.

This episode is full of valuable insights for software developers, managers, and leaders who want to understand why failure is so common in projects and how to build the kind of environments where teams can thrive.

This interview was recorded on August 25, 2025.

The full audio for the interview is here: https://s3.us-east-1.amazonaws.com/leanpub_podcasts/FM323-Max-Guernsey-III-2025-08-25.mp3. The Frontmatter podcast is available on our YouTube channel at https://www.youtube.com/leanpub, in Apple Podcasts here https://podcasts.apple.com/ca/podcast/frontmatter/id517117137, and almost everywhere else people listen to podcasts.