Great Books for Software Engineering Managers at Different Career Stages
Introduction
I have worked at Klaviyo for about a year and worked in the software industry for close to 16 years. My last 6 years have been as an engineering manager. For 14 years, while I was in college and starting my career, I was also a member of the Army National Guard where I served for 8 years as an officer. Through my experience in the Army and as a manager, continuous learning has been critical. It has helped me grow and adapt to the changing demands of every new role I was asked to take on.
Continuous learning is more important than ever for developing within your career. With greater access to information, AI tools like ChatGPT, and technology moving faster than we can possibly keep up, it is critical that we learn and refine our skills from the knowledge and experiences of others. Many things can be learned on the job, but it is critical that we also seek out information from outside our local sphere.
Learning can come in many forms and every person has a different preferred approach. For me the foundation of my learning has always been reading. Books hold in them the keys to knowledge that has been unlocked through the struggles and accomplishments of others. Not all books are created equal, some hold a wealth of information, while others provide a few pieces of advice padded with self promotion.
This post highlights books that I have found valuable in my time in management and leadership. The books included were each valuable to me because of something that has stuck with me from reading them and applying the knowledge gained. I have attempted to align these books with milestones in an engineering manager's career in hopes of helping others gain the same value.
Early Career: Laying the Foundation for Developing Leaders
Every path to becoming an engineering manager is different. Some seek out the opportunity and try to build a path to it. While others have it unwillingly thrust upon them when an organization has a need. Up to this point in my career I have not seen the “right” path, but have learned that a manager's success seems to be defined more by what they do once they get to the role than how they got there.
The journey does not end when a manager receives a title. The title is just the beginning of an adventure filled with new objectives and skills to learn. The managers that have the greatest success in the role early on, in my experience, acknowledge that they are in a new role. The actions they have taken to get where they are will need to change as they adapt to their new responsibilities. They accept that they need to keep learning and growing.
The following books were influential in my early career and journey to management.
Start with Why by Simon Sinek
Simon Sinek is synonymous with leadership and management. Many of his books could and should be on this list. When I was a young lieutenant in the US Army and just starting my career in software engineering this book was suggested to me by a mentor. I have read it a number of times and the core concepts it presents quickly became a foundation for how I lead and build teams.
The central theme of "Start with Why" is that inspiring leaders and organizations think, act, and communicate from the inside out, starting with their purpose or belief (the "Why"), then explaining how they fulfill that purpose, and finally describing what they do. People engage and gain a stronger sense of ownership of their work when they understand why they are doing it.
Sinek talks about the "Golden Circle" approach to leadership - Why, How, and What. He asserts that this approach aligns with how the human brain processes information and makes decisions. By clearly articulating and leading with your "Why," you can inspire others, build loyalty, and create a sense of belonging among team members and customers alike. This purpose-driven approach is particularly powerful in tech teams, where it can drive innovation, foster engagement, and align efforts towards a common goal.
The Manager’s Path by Camille Fournier
“The Manager’s Path” is one of those books I have gone back to time and time again. I recommend it to almost every engineer I mentor who has interest in leadership. I have also recommended it to senior engineers to help them better understand what their managers do and what they should expect from their managers. Camille Fournier does an excellent job outlining each level of management in an engineering organization. The knowledge shared in each chapter can then be used to provide a starting point as you leap into a new level of management.
For aspiring engineering managers or for early career managers this book can help answer one of the earliest questions of uncertainty, “What do I do now?”
The 7 Habits of Highly Effective People by Stephen Covey
"The 7 Habits of Highly Effective People" is a book that applies to many situations. Its application to engineering management is highlighted in the list of the 7 principles that Covey outlines.
- Be Proactive: Take responsibility for your life and actions
- Begin with the End in Mind: Define clear goals and vision
- Put First Things First: Prioritize and manage time effectively
- Think Win-Win: Seek mutually beneficial solutions
- Seek First to Understand, Then to Be Understood: Practice empathetic listening
- Synergize: Collaborate to achieve better results
- Sharpen the Saw: Continuously improve and renew yourself
Each principle is discussed in depth within the book, but the titles say a lot on their own. The principles that have stuck with me the most are “Seek First to Understand, Then to Be Understood” and “Be Proactive”.
As a manager, listening is one of your most important tools. Learning how to look past your initial reaction and seeking understanding from someone else will elevate your ability to collaborate. The ability to listen with intent will allow you to better support those who work with you and build better relationships with your peers.
Being proactive is critical to maintaining and excelling in your role as a manager. Reacting to every input is draining and causes a lot of churn in teams. Developing your skills around when and how to be proactive will elevate your work and your team's ability to succeed.
Mid-Career: Refining Your Skills
As you gain more experience as a manager the challenges you face and where you focus will shift. Certain tasks will become less challenging as you build out your toolkit with your experiences and learning. This shift in focus is a great time to begin to look outward from your team to the impact of others on your team’s success and how you track your team's performance. Two books that had a big influence on these topics are “The Power of a Positive No” and “Accelerate”.
The Power of a Positive No by William Ury
One of the hardest tasks an engineering manager will have to take on is saying no to a stakeholder or their team. If you do not say no on occasion you can easily find yourself and your team overloaded with more work than you could possibly complete. In some situations that overload will result in greater conflict as expectations grow on commitments you did not have the capacity to support.
On the other hand, saying no too often without well reasoned logic and proposals for alternative solutions will impact your relationship with those you work with. If we do not attempt to understand where others are coming from we may miss a critical opportunity to find a solution that will allow both parties to come away with a win.
"The Power of a Positive No" presents a framework for saying no while maintaining positive relationships. Ury argues that a "positive no" consists of three parts: affirming your own interests (the "yes"), clearly stating your refusal (the "no"), and proposing an alternative (the "yes" again). This framework, if applied in a thoughtful way, allows managers to set boundaries and protect priorities. For engineering managers, this skill is crucial in managing workloads, setting realistic expectations, and maintaining a healthy work environment.
This book came about in my career when I was managing a large number of stakeholders with requests that were all described as being urgent. The types of requests that are shared with a promise like “if you build X, I will sell Y!”, but lack the data needed to make a strong case. Our engineering team had very limited resources and we were already working on a packed roadmap with other work that had been requested with the same type of urgency. Many of the features we were releasing under this context were not performing as expected and we wanted to be more selective in how we spent our time. After reading this book and working closely with my product manager we began a campaign to work with the stakeholders to understand their needs, collaborate with them to collect qualifying data, and say yes to the right work. This led to a number of conversations where we said no to projects and used the data collected to educate the stakeholders on why we were saying no. “The Power of a Positive No” provided a valuable set of tools to navigate these conversations.
Accelerate by Nicole Forsgren, Jez Humble, and Gene Kim
"Accelerate" is a valuable book that presents research-based insights into high-performing technology organizations. Using data collected from many of the top tech companies in the industry at the time, it outlines key metrics for measuring organizational and team performance and explains why these metrics matter. The book emphasizes the importance of continuous delivery, lean management practices, and fostering a culture of learning and experimentation. For engineering managers, "Accelerate" offers a data-driven approach to assessing and enhancing team performance.
I recommend focusing on the sections about applying measurements in "Accelerate," only delving into the detailed analysis process if it interests you.
"Accelerate" was valuable to me when I began questioning how to measure success and performance within a team. It taught me to look beyond the obvious and use data to identify team-wide improvement opportunities. For example when I was first asked about how my team could do better I started by sharing all the things that I thought were in the way: excessive process, the bugs in the backlog, and the difficulty getting decisions made across multiple teams. Taking a step back and evaluating lead time, deployment frequency, mean time to restore, and change failure rate I was able to come to a different, more actionable set of conclusions. My team at the time suffered from issues getting work released. This led me to investigate why that was happening. Some of it was the development environment and part of that environment was within our control to change. We took a sprint to improve our local environment with better test data and removed a couple of steps to deploy changes and we were able to improve deployment frequency.
Long-Term Career: Strategic Thinking and Organizational Structure
As you gain experience as a line manager you will open up time to think about the long term. This will help unlock the next stages of management for you, which require more strategic thinking and analysis. The following are a couple of books that had an impact on how I approach building teams and collaboration with key leaders like product management.
Team Topologies by Matthew Skelton and Manuel Pais
“Team Topologies” explores how to structure and organize software development teams for optimal performance based on the state your organization is in its growth. It discusses 4 fundamental team types (Stream-aligned, Enabling, Complicated Subsystem, and Platform) and how they might interact (Collaboration, X-as-a-Service, and Facilitating). It then uses this structure to propose an organizational structure that can adapt to the changing needs of a business. It provides practical guidance on how to evolve team structures to meet changing business needs and technological landscapes, making it an essential read for engineering managers and organizational leaders seeking to improve their software delivery capabilities.
I found this book most useful as I moved into a role managing managers. It was enlightening as I considered how my teams would interact with other teams and how to best build out and hire for the missions my teams were trying to complete. “Team Topologies” provided a foundation that can be used to understand organizational shifts and evaluate why your team's performance might be in fact due to the organizational systems in place. Conway’s law suggests that our systems and architecture will naturally grow to match our organizational structure. “Team Topologies” provides insights on how to navigate this and build better software.
“Organizations which design systems (in the broad sense used here) are constrained to produce designs which are copies of the communication structures of these organizations.”
- Melvin E. Conway, How Do Committees Invent?
Empowered: Ordinary People, Extraordinary Products by Marty Cagan and Chris Jones
It is my opinion that in a product delivery organization every engineering manager should try to understand the role of the product managers they collaborate with. They should use this knowledge to build a strong partnership with product management. Product managers should be a part of the team and work closely with all of the engineers on the team. This will enable the team to collaborate more effectively over time.
“Empowered” is a comprehensive guide for product leaders in technology companies. It proposes an approach to product delivery called empowered product teams. The hypothesis is that empowered product teams can create innovative and successful products if given true ownership and autonomy. This can only be successful though if it is supported from the highest levels of leadership.
Engineering managers should consider reading this book to understand one approach to build strong, productive product delivery teams with an excellent foundation in ownership and autonomy. It is important to note that this is only one approach to product management. Cagan also has other helpful books about product management.
Conclusion
As an engineering manager, continuous learning and reading are not just beneficial—they're essential. The books discussed in this post represent just a fraction of the valuable resources available to guide you through different stages of your career. Each book offers unique insights, strategies, and perspectives that can significantly enhance your leadership skills, decision-making abilities, and overall effectiveness as a manager in the fast-paced world of software engineering.
Remember, the journey of an engineering manager is one of perpetual growth and adaptation. By consistently engaging with new ideas through reading and applying them in your daily work, you'll be better equipped to navigate the complexities of team dynamics, technological advancements, and organizational challenges. Embrace the habit of lifelong learning, and you'll not only improve your own capabilities but also inspire and empower your team to reach new heights of success and innovation.