Navigating the Challenges of Engineering Leadership: Insights from “An Elegant Puzzle” by Will Larson

Erik A. Ekberg
7 min readJul 7, 2023

In the world of hypergrowth technology startups, effective engineering leadership is a critical factor in driving success.

“An Elegant Puzzle,” written by Will Larson, offers invaluable insights and guidance on the journey towards becoming an exceptional engineering leader and manager.

Drawing from his own experiences at hypergrowth startups such as Uber and Stripe, Larson shares his story and imparts a wealth of knowledge in this opinionated book.

By delving into the intricacies of engineering management, Larson provides a roadmap for aspiring leaders to navigate the challenges and complexities of leading teams in rapidly evolving environments.

Photo of a black silhouette of a tree on a snowy white background by Fabrice Villard on Unsplash

Leading through Metrics

Metrics are the cornerstone of effective leadership, providing valuable insights into organizational workflows and materializing cause-and-effect.

Larson introduces two types of goals: investment and baseline goals.

Investment goals are aspirational targets and answer the question, “Where do we want to be?”

These goals are rooted in first-principles thinking and require leaders to experiment with opinionated policies, processes, and team dynamics to achieve.

Baseline goals represent the status quo and answer the question, “Where are we now?”

Baseline goals act as a counterbalance to investment goals, helping leaders identify and short circuit regressive behaviors.

By leveraging both investment and baseline goals, leaders can drive positive change within the organization with observable cause-and-effect to encourage adoption.

Photo of a graph with data points trending from “sucking in the past” to “not sucking in the future” by Isaac Smith on Unsplash

Making Change Easy

Change is inevitable, but it can often be met with resistance.

Leaders must create an environment where change is embraced rather than feared.

By facilitating a culture of experimentation and learning, leaders can encourage their teams to embrace new ideas and approaches.

Breaking down change into manageable steps, such as only introducing one change at a time, helps teams see, feel, and acclimate without being overloaded.

Additionally, by providing clear communication, historical context, and involving team members in decision-making, leaders can make change feel less disruptive and more empowering.

Leading Without Authority

Larson’s experience of leading without authority has revealed successful strategies for making change easy.

After setting clear goals, Larson recommends the following steps:

  1. Implement the change within a single team: By starting with a small-scale implementation, leaders can showcase the benefits and effectiveness of the proposed change.
  2. Measure the impact of the change on baseline and investment goals: Metrics and measurements play a crucial role in quantifying the impact of the change on the organization’s goals. This data-driven approach provides valuable insights into the effectiveness of the implemented change.
  3. Model and document how another team can adopt the change: Leaders should document the process and provide clear guidance on how other teams can adopt the change successfully. Sharing best practices and lessons learned facilitates a smooth transition for others.
  4. Share the learnings with the wider organization: Communication and transparency are essential when promoting change. By sharing the successes and learnings with the broader organization, leaders encourage progressive adoption and create a culture that embraces change.

Mandatory Change

Larson acknowledges that while decentralized leadership and change evangelism encourage teams to adopt changes at their own pace, there are times when change cannot be optional.

Technical migrations, for example, often require writing new code to address technical debt or replace deprecated third-party APIs.

To make these migrations successful, Larson offers the following recommendations:

  1. Conduct user testing on engineering teams to identify common use cases and ensure the new solution meets their needs.
  2. Create comprehensive and easily searchable documentation that provides step-by-step guidance on adopting the new standard. This empowers teams to navigate the migration process effectively and autonomously.
  3. Always allow engineering teams the ability to revert back to a working state if necessary, providing a safety net during the migration process.

Once the new standard is established, Larson emphasizes the importance of enforcing adoption through two key policies:

  1. Complete all new work using the new standard: By mandating the use of the new standard for any new work, leaders ensure consistency and prevent the proliferation of competing standards.
  2. Prioritize “done”: Larson places special emphasis on defining “done” for technical migrations. It entails achieving the adoption of the new standard throughout the entire codebase, including old and rarely touched code. This comprehensive adoption mitigates the infrastructure and cognitive costs associated with maintaining multiple competing standards, which can hinder the flow of work.

By following these strategies, leaders can make change more accessible, encourage widespread adoption, and minimize disruptions during technical migrations, ultimately facilitating a smoother flow of work within the organization long term.

Photo of leaves incrementally changing color from green to red by Chris Lawton on Unsplash

Using Policies to Focus

Larson emphasizes the importance of effective managers to write opinionated policies that focus the organization.

From a pragmatic perspective, opinionated and concrete policies prevent personal interruptions and eliminate real or perceived biases in value judgments.

Larson views policies as a means to align people with the company’s current strategy.

Much like goals, policies require frequent scrutiny to ensure they are having the desired impact.

Larson suggests collecting all exceptions to a policy as valuable feedback to inform policy changes because leaving outdated or ineffective policies unchecked can unnecessarily inhibit the flow or work.

By implementing and consistently reevaluating the impact of opinionated policies, leaders can enable teams to act autonomously in a way that aligns with the organization’s values and strategies.

Photo of a person reading a map to know where they are going and where they are now by Annie Spratt on Unsplash

Creating a Culture of Learning

Continuous learning is crucial for organizations to remain competitive in today’s rapidly evolving landscape.

Leaders play a vital role in fostering a culture of learning, where individuals are encouraged to acquire new skills, share knowledge, and challenge the status quo.

By building social networks and facilitating open conversations between people, leaders nurture relationships and enable the exchange of ideas.

Also, prioritizing the growth of others through mentorship and creating opportunities for career development empowers teams to adapt to new challenges and embrace growth.

One policy recommended by Larson in “An Elegant Puzzle” is to avoid relying heavily on specialists.

Specialists can become single points of failure and hinder long-term stability of the organization.

Instead, Larson suggests establishing a culture of peer-first learning, where knowledge is actively shared and not siloed through specialization.

Pairing junior and senior team members together facilitates this knowledge transfer and learning.

Additionally, Larson highlights the importance of succession planning, where managers actively work on being easily replaced as they are promoted up within the organization.

This ensures continuous growth and skill development throughout the managerial hierarchy.

Photo of people laughing at the same laptop screen by Priscilla Du Preez on Unsplash

Continuous Feedback

Establishing a culture of continuous feedback is essential for fostering growth and improvement within teams.

Leaders should prioritize providing constructive input to team members regularly, encouraging smaller, meaningful feedback sessions like one-on-ones instead of relying solely on formal performance reviews.

By offering timely feedback, leaders can address issues promptly and empower individuals to make necessary adjustments.

This practice cultivates psychological safety, enabling team members to take risks, learn from mistakes, and contribute to their fullest potential.

Another policy advocated by Larson is to assign both innovation (greenfield feature work) and technical debt (maintenance, bugs, etc.) to a single team.

This approach promotes code ownership and exposes team or individual weaknesses that can be addressed through experimentation or skill development, enhancing long-term flow.

By preventing a two-class system where one team handles “cool work” and another team is burdened with maintenance, siloing ownership to a single team ensures a more balanced and efficient approach to software development.

Photo of people working as a team by Anna Samoylova on Unsplash

Conclusion

In the rapidly evolving landscape of hypergrowth technology startups, effective engineering leadership is crucial for success.

“An Elegant Puzzle” by Will Larson offers invaluable insights and practical guidance for aspiring leaders seeking to navigate the complexities of engineering management.

By focusing on metrics, making change easy, using opinionated policies to enable autonomous decision making, fostering a culture of continuous learning, and continuous feedback, engineering leaders can drive growth and nurture a dynamic and innovative work environment.

Larson’s emphasis on managing change, enshrining code ownership with a single team, and the importance of succession planning further enriches the leadership strategies outlined in his book.

By following these principles and opinionated policies, leaders can cultivate a culture of growth, efficiency, and resilience within their own organizations, enabling them to thrive in the face of evolving challenges.

--

--

Erik A. Ekberg

Software engineer with a background in human psychology and data analytics who affords both customer and engineer delight through Agile software architectures.