The best books if you want to lead great software delivery teams

This book helped me set my initial approach to software development and I still periodically return to it for grounding.

An MIT project theorized that new-fangled PC software developers knew something mainframe and mini-computer makers didn’t. MIT’s research revealed something else entirely: Microsoft had uniquely effective ideas on how to build complex products in rapidly evolving competitive markets. Here is “agile” before it was put into the Manifesto in 2001, in a more complete form. Ever wonder where the idea of a team comprising functional specialists with overlapping roles, united by a common goal, came from? Or incremental feature evolution with periodic synchronization and constant testing? Early brilliance still of foundational relevance, in a coherent and engaging form.

Microsoft Secrets principles are great theory, but how do they feel in practice? Here is the Microsoft version of Tracy Kidder’s classic Soul of a New Machine.

A team of eager Microsoft engineers and product managers go for it, trying to build a children’s encyclopedia to extend the success of Microsoft’s earlier Encarta product. The genius of overlapping defined roles on a quest for a common goal comes face to face with the confusion, surprises, conflicts, diversions, disappointments, and elations inherent in most large-scale software programs trying to do something new (and aren’t they all?). Theory and intensely human practice come together.

I spent my career leading software engineering at two of America’s top banks. It’s not all innovative work, as you might guess, and here is where Toyota comes in. 

Toyota teaches the difference between routine, standardized work (where we use predictive process control) and creative work (where we use adaptive process control). Balancing this in practice is a key to being a great software engineering leader. For those manufacturing-like processes (incremental feature addition, defect repair) the Toyota manufacturing way became the basis of the Agile movement a decade later: flow, pull, level work, quality the first time, process standardization and continuous improvement, and closeness to customers. Toyota Way provides a deeper understanding than any agile seminar. 

When this book was released, I was immersed in a huge failing project at Wells Fargo, struggling to make sense of it all. This book helped me put the failure in perspective and showed a better way that I embraced for the rest of my career. 

The key insight is that large-scale innovation is not like manufacturing – it is less about planning and control, more about people, rapid learning, and adaptation. Here we learn concepts such as the Chief Engineer, lightweight milestone—and responsibility-based project management, and focusing on engineering skills and vendor partnerships. Shelve the elaborate process frameworks consultants are selling you, focus on the basics Toyota emphasized throughout their glory years. 

Fast-forward to today, and Team Topologies provides the shortest, clearest direction on how to arrange your business for technology engineering success. Skelton and Pais provided me a documented, sharable answer to “how do we do a digital transformation,” one of the common challenges organizations are facing today. 

Too many enterprises lead with technology (“we need a new mobile app”) or process (“let’s do agile”).  This ignores the centrality of people to success, which we saw so clearly in I Sing. Skelton and Pais start with the basics of how large-scale work is done today (mostly in teams), how teams work based on trust, and then go on to define the types of teams (just a few!) and their most effective interactive modes. Everything revolves around the flow/delivery teams, bringing us all the way back to Toyota Way’s admonition to engineer the flow.