Principles for Leading Software Teams: A Guide

The Articles

As I continue to enumerate my ideas on how to organize and manage a software team, I thought it might be useful to list the posts in one place — a table of contents of sorts. To that end, here are the posts in the order I think it makes most sense to read them:

• The Goals of a Software Organization
• Feeling Safe at Work
• Stress Robs You of Your Ability to Think Strategically
• It’s About the Journey — Not the Destination
• Embracing the Journey
• It’s the Culture, Stupid!
• There Is No Individual
• Autonomy? You Can’t Handle Autonomy!

Reference Materials

Additionally, I have had a few people say that it would be nice if I called out my reference material in one place. This is my attempt to list the materials that have been influential on my thinking along with a bit of commentary.

Holacracy: The New Management System for a Rapidly Changing World
The “textbook” on the managerless organizational system known as Holacracy. This was really the book (and process) that opened my eyes to a different way of thinking about work. Even if you don’t plan to implement Holacracy, it’s a great book that will transform the way you think about organizing. It is getting a bit dated as that system continues to evolve.

Drive: The Surprising Truth About What Motivates Us
As far as I’m concerned, this is the book on modern/evolved management thinking. I would consider this and Culture Code required reading for anyone in management (not just managing software teams).

The Culture Code: The Secrets of Highly Successful Groups
If Drive is about the individual, Culture Code is about the system. It’s a great book. Required reading.

Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity
I have mixed emotions about this book. On the whole, I would recommend it; but there are a number of places where “unevolved” management thinking slips in. On the other hand, it’s a sort of handbook of effective and practical management ideas. I have adopted a number of them.

WorkLife with Adam Grant
Very informative podcast by organizational psychologist Adam Grant (author of Give and Take among other books). I find podcasts to be a great way to keep my thinking fresh and innovative, and this one rarely disappoints.

EconTalk
Ironically, many of my ideas on management come from economics, and this podcast has taught me so much in that regard. Beyond that, the host Russ Roberts is the rare academic that could still claim the title Renaissance Man in my opinion: He’s just as at home discussing Jane Austen with a literature professor as he is quoting Adam Smith to a fellow economist. I cannot recommend this podcast enough. I don’t think it’s a stretch to say I take away actionable information at least 50% of the time.

Hidden Brain
A podcast that examines human behavior. Really insightful stuff that has informed some of my thinking about organizational/interpersonal dynamics.

Beyond Empowerment: The Age of the Self-Managed Organization
A fictionalized account of the evolution of The Morning Star Company into an organization without managers. Encouraging to read if you aspire to have a flat organization.

Crucial Conversations: Tools for Talking When Stakes Are High
Since software organizations are systems of people, it’s critical that the communications between those people be as open, honest, and effective as possible. This book does a great job of giving you the necessary tools.

The Tyranny of Metrics
Great book. The modern organization is so obsessed with measuring that it drives us to do really counter-productive things. The author lays out the anti-patterns created by this obsession which can help you avoid common pitfalls. Read this along with Accelerate to get a good handle on how to measure your organization in a safe and healthy way.

Give and Take: Why Helping Others Drives Our Success
This book is a little bit out of place. It’s more about personal development than organizational thinking. That said, I still found it to be very formative in how I think about motivation and personal development within an organization. I recommend it mostly because it gave me the perspective that “giving” wins in the long run which was very liberating and helped me to be much less selfish with my time. That has made my career more fulfilling and, I would claim, more successful.

Accelerate: Building and Scaling High Performing Technology Organizations
This book should be required reading for any software professional. It is a thorough, academic study on what factors correlate to a high performing technology organization. The authors make some really great points regarding organizational culture and practice. Most engineers will read it and say, “That’s what I’m talking about!” It’s stuff you probably already intuitively know, but this arms you with the data.

The Fearless Organization: Creating Psychological Safety in the Workplace for Learning, Innovation, and Growth
I was under the impression that this book offered “recipes” to follow for creating psychological safety. That didn’t quite pan out. It’s a good and thorough treatment of the topic, but I didn’t feel like I learned much beyond what I had picked up from articles and podcasts on the topic.

Creativity, Inc.: Overcoming the Unseen Forces that Stand in the Way of True Inspiration
Enjoyable read about Ed Catmull’s journey from talented creator to organizational leader. Lots of wisdom.

Team Topologies: Organizing Business and Technology Teams for Fast Flow
What if someone did a deep dive on the principles of Agile and the reality of Conway’s Law to see what kind of organizational structure it would lead to? That’s this book. It goes hand in hand with Accelerate in my mind. I would have liked to see them spend some time talking about what an actual org chart should look like to accommodate this way of thinking. I certainly have my own opinions but would have loved to hear theirs.

Podcasts

Open Source CXO was kind enough to have me on their podcast. It covers some of the topics I write about here on Medium. There are two episodes:

• Episode 19: What the Holacracy? The Basics & Benefits of Flat Organizations in Development
• Episode 20: The Data-Backed Benefits of In-Person Development Teams

Important Context

Much of my content is firmly in the space of social science. Therefore it’s good to be aware of a relatively recent development. Due to some deeper introspection starting around 2010, the social sciences stumbled into a crisis. Many of the studies that reached conclusions which were being taken for granted could not be replicated. That’s kind of important given that replication is a crucial part of the scientific method. If you’re interested, this is a great conversation on the topic. The fallout for me is that I try to maintain a healthy skepticism when I am reading about studies in the social sciences.