Books on Leading Software Development

Business | 2024-02-10. 5 min read (1106 words).

These are my top book recommendations on leading high-performance software development organisations. As a bonus, I also link to related online resources and videos for shorter summaries of the key ideas.

Topics:

Introduction

There are a lot of good books about this, but most people have limited time to read. My goal here is to give prioritised recommendations of the very best books I know for anyone who wants to learn about organising and leading software product development well. I read a lot and these are all books that I have read at least once (often many times) and find absolutely outstanding.

By software product development, I mean software development and operations of ‘software products’ in a wide sense. Many general principles apply in all these situations. The top 5 books are the best general books to quickly get as much modern knowledge of this as possible in my opinion. I also recommend a few books on different specific topics for diving deeper.

For those with even less time or as a complement, I also link to some online resources and videos. These are great to show your teams too!

I’m using these books myself to brush up before starting a new job as CTO.

Top 5 books

In order of priority, these are my recommendations:

1. EMPOWERED: Ordinary People, Extraordinary Products by Marty Cagan.
   • Leadership lessons from the product management expert Marty Cagan on product and engineering leadership. I wish more people read this!
2. Team Topologies by Matthew Skelton and Manuel Pais.
   • Describes how to organise software development teams for enabling empowered teams in a team-first organisation.
3. Radical Focus - Second Edition by Christina Wodtke.
   • Introduction to OKRs for goal-setting across empowered teams.
4. Doing Agile Right by Darrell Rigby, Sarah Elk, Steve Berez.
   • Great insights on how to succeed with agile and avoid common pitfalls.
5. The DevOps Handbook - Second Edition by Gene Kim, Jez Humble, Patrick Debois, John Willis, Nicole Forsgren.
   • Great introduction to DevOps, which is another essential concept.

These are in order of priority. If someone wants to read fewer books, I would recommend starting from the top. Even the first book by Marty Cagan alone gives a great overview of most topics covered in the other books and will help anyone improve regardless of previous knowledge level.

Special topics

Here are additional book recommendations for specific topics to complement the above ones, in no particular order. These are my top recommendations for learning more about each topic. There are many topics left out here, so it is by no means complete.

Recommendations by topic:

• Foundational management:
  • HBR Manager’s Handbook: The 17 Skills Leaders Need to Stand Out.
    • Great overall book about management and leadership skills.
  • Being the Boss: The 3 Imperatives for Becoming a Great Leader by Linda A. Hill and Kent Lineback.
    • Does a great job at explaining what it’s all about.
• Scaling empowered teams:
  • One Mission: How Leaders Build a Team of Teams by Chris Fussell and C. W. Goodyear.
    • Describes how the US military adopted a team-of-teams model of empowered teams that collaborate in order to respond fast enough to the constantly changing modern battlefield. Very transferable.
  • Measure What Matters: How Google, Bono, and the Gates Foundation Rock the World with OKRs by John Doerr.
    • Another good book about OKRs. One of the most famous ones.
• Agile:
  • Essential Scrum: A Practical Guide to the Most Popular Agile Development Process by Kenny Rubin.
    • One of the best books for learning all the basics of Scrum.
  • Scrum: The Art of Doing Twice The Work In Half the Time by Jeff Sutherland.
    • From one of the creators of Scrum, this gives the ideas behind it.
  • A Scrum Book: The Spirit of the Game by Jeff Sutherland, James O. Coplien, and The Scrum Patterns Group.
    • Presents patterns for applying Scrum. Deep dives into specifics.
• Product management and business:
  • INSPIRED: How to Create Tech Products Customers Love - Second Edition by Marty Cagan.
    • The go-to book for basic product management knowledge.
  • The Lean Product Playbook by Dan Olsen.
    • Another great book on product management, which is more concrete.
  • The Lean Startup by Eric Ries.
    • A classic that is useful everywhere.
• Software architecture, automated testing, DevOps:
  • Software Architecture in Practice - 4th Edition by Len Bass, Paul Clements, Rick Kazman.
    • One of the best introductions to software architecture.
  • Accelerate: Building and Scaling High Performing Technology Organizations by Nicole Forsgren, Jez Humble, Gene Kim.
    • Presents research on DevOps and other aspects of high-performance software development organisations.
  • Effective software testing by Maurício Aniche.
    • My standard recommendation to learn about automated tesing.

Web resources

These resources are useful to gain knowledge related to the books recommended above:

• Related to EMPOWERED and INSPIRED:
  • Silicon Valley Product Group (svpg) articles.
• Related to Team Topologies:
  • Learning for Team Topologies.
  • DevOps Topologies.
• Related to Radical Focus:
  • Eleganthack by the author Christina Wodtke.
• Related to Doing Agile Right:
  • Bain & Company’s book site.
  • HBR articles from (some of) the authors:
    • Agile at Scale.
    • Purposeful Business the Agile Way.
    • The Agile C-Suite.
  • Agile Academy: Doing Agile Right: Darrell Rigby.
• Related to DevOps Handbook and Accelerate:
  • DevOps Research and Assessment (DORA).
• Related to Being the Boss:
  • HBR: Becoming the Manager by the same author.
• Related to One Mission:
  • McChrystal Group: Team of Teams.
• Related to Measure What Matters:
  • Measure What Matters website.
• Scrum and agile resources:
  • Agile manifesto.
  • Scrum Guide.
  • Scrum Pattern Group.
  • Scrum@Scale.
• Related to The Lean Product Playbook:
  • The Lean Product Playbook website.
• Related to Software Architecture in Practice:
  • ADD 3.0: Rethinking Drivers and Decisions in the Design Process.
• Related to Effective Software Testing:
  • The book’s website.
  • xUnit Test Patterns website. An older good book with a nice website.

Recommended videos

Here are a few recommended video talks related to the topic, which are partially based on the books:

• EMPOWERED - Achieving Extraordinary Results with Ordinary People - Marty Cagan.
• Product Management: “Beyond Lean and Agile” by Inspired author Marty Cagan at Lean Product Meetup.
• The Lean Product Playbook with Dan Olsen in Silicon Valley.
• How and Why to Design Your Teams for Modern Software Systems - Matthew Skelton.
• The Key to High Performance: What the Data Says - Dr. Nicole Forsgren.
• HBR: What Makes a Great Leader?.
• What is an OKR? Andy Grove, OKR inventor, explains.
• Why the secret to success is setting the right goals | John Doerr | TED.
• The ultimate guide to OKRs | Christina Wodtke (Stanford).
• Doing Agile Right with Steve Berez and Darrell Rigby.
• Scrum: How to do twice as much in half the time | Jeff Sutherland | TEDxAix.
• Chris Fussell, McChrystal Group: High Performing Teams.