The engineering mindset | Will Larson (Carta, Stripe, Uber, Calm, Digg)

The engineering mindset | Will Larson (Carta, Stripe, Uber, Calm, Digg)

Engineering Leadership and Evolution

In this section, the discussion revolves around treating engineers as responsible adults rather than sheltering them from critical tasks to help them grow professionally.

Engineers' Growth and Responsibilities

  • Engineers should be given responsibilities to thrive as adults. Sheltering them from important tasks is not beneficial for their growth.

Treating Engineers as Peers

  • There is a shift towards treating engineers as peers and placing them in senior leadership roles without coddling or shielding them from real challenges.

Introduction of Will Larson

This part introduces Will Larson, the CTO at Carta, highlighting his experience in software engineering leadership and authorship of essential books for engineers.

Introduction of Will Larson

  • Will Larson is the CTO at Carta with a background in software engineering leadership at companies like Stripe, Uber, and Comm.

Accomplishments and Publications

  • Author of two essential books for engineers: "An Elegant Puzzle" and "Staff Engineer."
  • Upcoming release of his newest book, "The Engineering Executives Primer" in February next year.
  • Regularly publishes insightful content on his blog at lane.com.

DX: Developer Productivity Platform

The segment discusses DX, a platform designed to measure and enhance developer productivity by providing qualitative and quantitative insights.

Introduction to DX Platform

  • DX is a platform created by researchers behind frameworks like Dora space and devx to improve developer productivity.

Features of DX Platform

  • Combines qualitative and quantitative insights for a comprehensive view of developers' performance.
  • Used by startups and Fortune 500 companies including Twilio, eBay, Rex Toast Fiser, Proctor & Gamble.

One Schema: CSV Importer Solution

This part showcases One Schema's solution for handling messy data through an embeddable CSV importer tailored for SAS customers.

One Schema's Solution

  • One Schema offers an embeddable CSV importer designed to handle messy data efficiently.

Benefits of One Schema

  • Companies like Scale AI and Pave utilize One Schema to streamline spreadsheet import experiences.
  • Intelligent correction of messy data reduces customer frustration with data processing.

Engineering Team Allocation and Evolution

The discussion revolves around the evolution of engineering team allocation, the changing dynamics within teams, and the shift towards treating engineers as peers rather than sheltering them.

Evolution of Engineering Teams

  • Companies are now focusing on determining the right allocation and sizing of engineering teams, a topic that was previously not extensively discussed.
  • There is a significant shift where teams are being restructured, reduced in size, or consolidated, marking a departure from previous practices.
  • Engineers used to have more leverage within companies; however, there has been a change in how engineers are perceived and treated within organizations.

Treating Engineers as Peers

  • A call to treat engineers as adults rather than children by providing them with responsibilities and opportunities to thrive.
  • Emphasizing the importance of putting engineers into senior leadership roles without coddling them or shielding them from real challenges.

Accountability and Senior Roles for Engineers

The conversation delves into the changing dynamics regarding upsetting engineers, accountability within engineering teams, and the transition towards holding engineers accountable for their work.

Shifting Dynamics

  • Leaders may not need to worry as much about upsetting engineers due to changes in evaluation criteria.
  • In the past era, hiring and retention were crucial metrics leading to coddling of engineers which hindered growth opportunities for both individuals and organizations.

Accountability for Growth

  • Providing engineers with challenging problems fosters accountability and enables their progression into senior roles.
  • The importance of holding engineers accountable to facilitate their advancement into senior positions where they can contribute effectively.

Systems Thinking in Problem-Solving

Exploring systems thinking in problem-solving contexts using an incident management example from Stripe to highlight potential pitfalls when overly reliant on this approach.

Systems Thinking Pitfalls

  • Advocacy for systems thinking but caution against becoming too entrenched in frameworks without considering practical outcomes.
  • Illustration through an incident management scenario at Stripe where excessive focus on analysis led to overlooking actual improvements.

Balancing Analysis with Action

  • Acknowledging that conflicts between systems thinking models and reality can impede progress if not managed effectively.

Incidents and Systems Thinking

In this section, the speaker discusses incidents, remediation processes, mental models, and the importance of practical application alongside learning. Additionally, systems thinking is introduced as a concept focusing on stocks and flows within a system.

Understanding Incidents and Mental Models

  • The process of remediating incidents allows for quick modeling and understanding where mental models conflict with reality.
  • Emphasizes the need to balance learning with practical application in order to truly understand concepts.

Introduction to Systems Thinking

  • Systems thinking involves considering stocks (accumulations) and flows (movements between stocks) within a system.
  • Stocks can be exemplified by the number of fish in a lake, while flows represent factors like fishing rates impacting stock levels.

Systems Thinking Application: Hiring Pipeline

This part delves into applying systems thinking to a hiring pipeline scenario, illustrating how stocks (candidates) and flows (recruitment stages) interact within the system.

Modeling a Hiring Pipeline

  • Initial step involves creating a model that includes potential candidates as stocks and various inflows such as sourcing channels.
  • Conversion rates at different stages of recruitment process highlight how candidates progress through the pipeline.

Identifying Pipeline Issues

  • Challenges often arise when hiring managers struggle to make confident hiring decisions or extend offers effectively.
  • Common problems include an excess of candidates reaching offer stage without successful conversions or insufficient candidate inflow.

Utilizing Data for Optimization

  • Analyzing historical data from applicant tracking systems helps identify bottlenecks or inefficiencies in the hiring process.

Engineering Strategy and Product Management

In this section, the discussion revolves around the importance of having a systematic approach in product management and engineering strategy. The conversation touches upon how strategies are often not explicitly written down but still exist within organizations.

Importance of Systematic Approach in Product Management

  • Product managers may not naturally work in a systematic way as they often think in funnels.
  • Emphasizes the significance of following the stock through different steps to understand the flow effectively.

Engineering Strategy Insights

  • Engineers tend to overlook engineering strategy compared to other functions that have well-defined strategies.
  • Highlights the need for Engineers to focus more on developing an engineering strategy.

Clarity on Company Strategies

  • Challenges the notion that every function within a company has a clear strategy, suggesting that it is often not explicitly documented.
  • Stresses that even if strategies are not formally written down, they still exist within teams and departments.

Defining Strategy and Its Components

This part delves into defining what constitutes a strategy according to Richard Rumelt's perspective. It outlines three key components essential for crafting effective strategies.

Richard Rumelt's Definition of Strategy

  • Introduces Richard Rumelt's definition of strategy from his book "Good Strategy Bad Strategy."
  • Outlines three fundamental components: diagnosis, guiding policies, and actions.

Components of Effective Strategies

  • Diagnosis involves understanding the current status quo.
  • Guiding policies are based on diagnosis and determine how challenges will be addressed.

Innovative Engineering Strategies

In this section, the speaker discusses the importance of innovative engineering strategies and provides examples from Uber and Stripe to illustrate effective strategic decisions in engineering.

Concerns about Inert Strategy

  • The speaker expresses concern about ineffective strategies that involve deprecating old product features without actual implementation.
  • Contrasting views are presented where the speaker is less worried about such strategies, emphasizing their role in clarifying future decision-making processes.

Examples from Uber

  • At Uber, a shift from using data centers to embracing the cloud was highlighted as a significant change in strategy over time.
  • The strict no-cloud policy at Uber led to challenges but also enabled rapid expansion into new markets like China within three months due to self-reliance on infrastructure.

Strategic Decision Making at Stripe

  • Stripe's focus on running a Ruby monolith encouraged engineers to prioritize innovative feature development for users over creating diverse tooling for different programming languages.
  • Despite initial resistance from engineers, both Uber and Stripe's strategies effectively directed limited resources towards solving key problems rather than pleasing everyone.

Effective Strategy Implementation

This section delves into the concept of effective strategy implementation by emphasizing constraints, accurate diagnosis, and coherent guiding policies.

Embracing Constraints

  • Effective strategies revolve around constraining options to accelerate progress and concentrate efforts on critical issues.
  • Solving constraints is crucial in strategy implementation as it enables a focused approach towards addressing core challenges efficiently.

Identifying Bad Strategies

  • Bad strategies often stem from inaccurate diagnoses or individuals imposing personal desires onto constraints, leading to incoherent guiding policies.

Enhancing Strategic Thinking

This segment explores avenues for improving strategic thinking through recommended readings and resources for honing strategic skills.

Resources for Strategic Development

  • Recommended books include "Good Strategy Bad Strategy" by Richard Rumelt as an essential starting point for understanding effective strategy formulation.
  • Engaging with systems thinking through books like "Thinking in Systems" can enhance one's ability to model reality accurately for improved strategic diagnosis.

Engineering Strategy Literature

  • Notable engineering strategy books like "Technology Strategy Patterns" offer valuable insights into crafting effective engineering strategies.

Writing and Career Impact

In this segment, the speaker discusses the impact of writing on their career, emphasizing the importance of writing what energizes them rather than focusing solely on popular topics or financial gain.

Writing for Passion

  • Writing what you want to write allows for more productivity and fulfillment.
  • Avoiding writing for financial gain enables freedom in choosing topics based on personal interest.

Writing Schedule and Energy

  • Writing on a schedule can be draining when topics do not align with personal interests.
  • Owning the schedule and writing about energizing topics enhances productivity and creativity.

Writing Approach and Content Creation

  • The speaker emphasizes writing where there is energy to maintain a positive mindset.
  • Diligently anticipating concerns allows for content reuse, especially in certain book genres.

Content Creation Strategies

This part delves into the speaker's approach to content creation, focusing on writing what energizes them while disregarding uninteresting topics or audience expectations.

Energizing Content Creation

  • Emphasizes writing based on personal interest and energy levels over catering to an audience.
  • Acknowledges that not all readers may resonate with personal interests, which is acceptable.

Maintaining Creativity in Content Creation

Here, the discussion centers around maintaining creativity by focusing on topics that genuinely excite the writer rather than following trends or external pressures.

Prioritizing Personal Interest

  • Advises against creating a job out of content creation by solely chasing popular trends.
  • Stresses the importance of authenticity in content creation to prevent burnout and dissatisfaction.

Detailed Discussion on Writing and Time Management

In this segment, the speaker discusses the misconceptions around starting in a saturated market like podcasts or writing platforms. The importance of consistency and quality over time is emphasized.

Too Many Podcasts and Writers

  • Starting late in a crowded field is discouraged.
  • Building an audience through consistent quality content is highlighted.
  • Transitioning audiences across platforms is deemed crucial for success.

Navigating Long-Term Commitment in Content Creation

The conversation shifts towards long-term commitment in content creation, emphasizing the challenges of sustaining efforts over time.

Long-Term Commitment

  • Emphasizes the difficulty of committing to endeavors for extended periods.
  • Personal experiences with Substack and podcasting are shared.
  • Success hinges on perseverance and continuous effort rather than immediate results.

Understanding the Infinite Game of Content Creation

The discussion delves into the concept of an infinite game in content creation, highlighting collaboration over competition and sustained effort as key factors for success.

Infinite Game Mentality

  • Success defined by continuous dedication rather than reaching an endpoint.
  • Collaboration among creators fosters growth collectively.
  • Emphasizes maintaining a high standard to stand out amidst increasing content volume.

Balancing Work, Writing, and Energy Management

Practical strategies for balancing work commitments with writing pursuits are explored, focusing on aligning writing topics with professional interests for efficiency.

Work-Writing Balance

  • Aligning writing topics with work responsibilities enhances productivity.
  • Writing about related topics aids in refining thinking and performance improvement.
  • Scheduling dedicated time for writing while considering energy levels is crucial for consistency.

Overcoming Procrastination Through Passion

Addressing procrastination through passion-driven writing endeavors is discussed, emphasizing intrinsic motivation as a key driver for consistent output.

Passion as Motivation

  • s Excitement fuels finding time and energy for writing endeavors.
  • Aligning passion with subject matter enhances productivity and engagement.

Advancing in the Industry and Writing Consistently

In this section, the speaker discusses strategies for advancing in the industry and maintaining consistency in writing.

Strategies for Advancement and Consistent Writing

  • Emphasizes the importance of publishing consistently rather than hoarding drafts.
  • Advocates for publishing almost everything written to improve accuracy over time.
  • Focuses on personal growth as a writer rather than perfection or reader experience.
  • Highlights the value of sharing experiences as an operator with active learning.
  • Recommends focusing on quantity over quality initially, disregarding trivial feedback.

Building Productive Relationships Between Product Managers and Engineers

This part delves into challenges faced by product managers in fostering positive relationships with engineers and engineering managers.

Overcoming Core Problems

  • Identifies misaligned incentives as a common issue between product managers and engineers.
  • Discusses how misalignment can stem from differing priorities like timelines or sales pressure.
  • Emphasizes understanding complex incentives rather than creating simplistic narratives of blame.
  • Stresses the importance of comprehending each other's needs before attempting conflict resolution.

Incentives and Performance Reviews

The discussion revolves around aligning performance reviews for product managers (PMs) and engineering managers (EMs) to ensure fairness and shared incentives.

Aligning Performance Reviews

  • EM-PM pairs generally have the same performance rating, except in clear non-performance cases.
  • Challenges arise when two competent individuals struggle with overall execution; aligning their ratings drives a shared perspective.
  • Implementing a unified scoring system for EMs, PMs, and business leadership based on problem-solving abilities across constraints fosters alignment.
  • EM and PM receive the same performance review rating, discussed jointly in meetings for calibration.
  • Transparency about shared incentives between EMs and PMs enhances understanding and collaboration.

Balancing Work Priorities

Addressing challenges faced by engineering managers in providing engaging work while balancing team expectations.

Balancing Work Priorities

  • Historical challenge: EM's role of assigning interesting work clashes with team preferences, especially evident in growth teams.
  • Struggles arise when EM must prioritize mundane tasks over innovative projects desired by engineers, leading to friction.
  • Communication gaps between PM and EM regarding task prioritization can create misunderstandings; honest conversations are crucial.

Measuring Engineering Productivity

Exploring methods to measure engineering velocity and productivity amid industry pressures for efficiency.

Measuring Productivity

  • Increasing focus on measuring productivity due to team size reductions; pressure from stakeholders to demonstrate efficiency.

New Section

In this section, the speaker discusses the challenges of determining appropriate allocation of funds within a company, particularly focusing on R&D and engineering expenses.

Prioritizing Resource Allocation

  • Determining how much to spend on R&D and engineering is crucial for companies.
  • "How much should we be spending on R&D, how much should we be spending on engineering?"
  • Benchmarking these allocations can provide guidance but may not lead to effective decision-making.
  • Using benchmarks may not necessarily help in running the organization effectively.
  • Engaging with the team directly can offer valuable insights into the effectiveness of R&D and engineering efforts.
  • Good leaders can gauge team effectiveness by communicating with engineers.

Effective Engineering Evaluation

This part delves into strategies for evaluating the effectiveness of R&D and engineering teams within an organization.

Assessing Team Effectiveness

  • Effective leadership involves aligning engineering evaluation with business and product goals.
  • Aligning evaluations with product goals ensures accountability and support for customers.
  • Demonstrating tangible achievements through a roadmap can enhance understanding and support from stakeholders.
  • Showcasing impactful accomplishments over time fosters confidence and trust.

Metrics in Engineering Management

The speaker explores the significance of metrics in evaluating team performance in engineering management.

Utilizing Metrics

  • "Accelerate" by Nicole Forsgren, Jez Humble, and Gene Kim introduces key metrics like lead time, incident remediation time, failure rate, etc., for assessing team performance.
  • The book presents essential metrics that many startups use to evaluate their teams.
  • While metrics provide diagnostic insights, they do not define overall company success or failure.
  • Metrics guide improvement areas but do not determine organizational excellence.

Importance of Measurement

Emphasizing the value of measurement despite imperfections in data accuracy within organizations.

Embracing Imperfect Measurement

  • Encouraging a culture of measurement even if data may not be perfect helps in tracking progress effectively.

Metrics and Data Analysis

The discussion delves into the importance of metrics in understanding data, emphasizing the value of starting with basic metrics for diagnosis and reporting purposes.

Importance of Metrics

  • Metrics provide insights into the reality of rich data, not just perfect datasets.
  • Basic DOR (Duration, Frequency, and Lead Time) metrics serve as a helpful starting point for diagnosis and reporting to executives.

Company Values and Culture

Exploring the significance of company values in shaping organizational culture and decision-making processes.

Defining Company Values

  • Company values play a crucial role in defining organizational culture.
  • Emphasizes the need for honesty in aligning actions with stated values.
  • Values should be applicable to real-world scenarios to guide decision-making effectively.

Effective Company Values

Discussing characteristics that make company values effective and impactful within an organization.

Characteristics of Effective Values

  • Honest execution of stated values is essential for credibility.
  • Applicability ensures that values can guide decisions practically.

New Section

In this section, the speaker discusses the importance of having a clear understanding of who does not fit within a group or organization to ensure effective cohesion and identity.

Clear Identification of Non-Fit Individuals

  • It is crucial to identify individuals who do not align with the group's values or culture.
  • Having a clear distinction of who does not belong can serve as a hiring filter, aiding in selecting suitable candidates.
  • If certain values do not apply to anyone in the organization, they become redundant and should be eliminated for clarity and coherence.

New Section

This segment delves into the significance of unique values that define an organization's identity and differentiate it from others.

Uniqueness in Organizational Values

  • Merely common values like integrity are insufficient; uniqueness sets organizations apart.
  • Values should reflect who the organization truly is rather than aspirational ideals.

New Section

The speaker shares a personal anecdote about revising organizational values based on practicality and authenticity.

Revising Organizational Values

  • Values should accurately represent the organization's capabilities rather than desired traits.
  • Example shared where two values were removed due to lack of alignment with actual practices.

New Section

The speaker recounts a challenging experience with a project rewrite at Dig, highlighting key lessons learned from failure.

Lessons from Project Rewrite at Dig

  • Need for adapting to market changes such as social components to remain competitive.
  • Challenges faced during a complete rewrite leading to valuable insights on decision-making processes.

New Section

Reflecting on personal experiences during project challenges and learning from failures in real-world scenarios.

Learning from Failure Experiences

  • Personal account of challenges faced during project rewrites and leadership transitions.

The Journey of a Startup: Challenges and Learnings

The speaker reflects on the challenges faced during the early days of a startup, highlighting experiences of server overload, layoffs, and personal growth amidst adversity.

Challenges Faced in Early Days

  • Encountered server overload issues leading to a remarkable learning experience.
  • Team downsized significantly within months due to layoffs, shaping the speaker's perspective on career beginnings.
  • Became an engineering team manager despite lack of qualifications, emphasizing the value of learning through challenging opportunities.
  • Acknowledges that difficult moments often turn into valuable teaching experiences when reflected upon.

Navigating Business Challenges and Learning from Failures

The speaker discusses how challenging experiences can lead to significant growth and bonding within teams, emphasizing the power of overcoming obstacles together.

Embracing Challenges for Growth

  • Reflects on challenging experiences as pivotal moments in one's career journey.
  • Highlights the importance of facing difficulties with respected colleagues for powerful shared achievements.
  • Recalls the struggles during Uber China migration as remarkable learning opportunities despite initial reluctance.

Lessons Learned from Startup Setbacks

The speaker reflects on setbacks faced by their startup, particularly focusing on technical challenges and business implications.

Startup Setbacks and Learning

  • Describes a month-long period where platform functionality was severely impacted by technical issues.
  • Acknowledges that while setbacks occurred, valuable lessons were learned from overcoming challenges as a team.

Factors Influencing Startup Success

The discussion delves into critical factors contributing to startup success or failure, focusing on product-market fit and monetization strategies.

Product-Market Fit and Monetization Strategies

  • Attributes Dig's decline to SEO-driven changes affecting monetization strategies negatively.
  • Discusses Dig's innovative ad format ahead of its time but hindered by SEO traffic changes impacting revenue generation.

Upcoming Book Release: Engineering Executives Primer

The speaker introduces an upcoming book tailored for engineering executives and individuals seeking insights into working with tech leadership roles.

Introduction to New Book

  • Teases about an upcoming book release titled "Engineering Executives Primer" scheduled for February launch.
  • Provides details on where to find the book online before its official release date.

Target Audience for Engineering Executives Primer

The speaker clarifies the target audience for the new book aimed at aiding individuals in understanding engineering executive roles better.

Target Audience Clarification

Detailed Insights from the Transcript

In this section, the speaker discusses book recommendations, favorite TV shows, interview questions for job candidates, life mottos, underappreciated writings, and where to find him online.

Book Recommendations

  • ** Thinking Systems: A Primer:** Recommended as a thought-provoking read.
  • ** Good Strategy Bad Strategy:** Suggested for insights into strategy formulation.
  • ** Don't Think of an Elephant by George Lakoff:** Highlighted as an interesting book on framing concepts.

Favorite TV Show

  • ** Top Chef:** Enjoyed with the speaker's wife for its structured format and escapism from real-life stress.

Interview Questions

  • ** Candidate Selection Criteria:** Focuses on helping candidates choose the right job offer based on their preferences and values.

Life Mottos

  • ** Navigating Challenges at Uber:** Emphasizes perseverance through challenges without avoidance.
  • ** Decision-Making Importance:** Urges prioritizing decisions based on long-term impact rather than short-term stress.

Underappreciated Writing

  • ** "Hard to Work With":** Explores the challenge of maintaining high standards without being perceived negatively in a work environment.

Online Presence and Engagement

  • ** Website Link for Contact:** Provided link to personal website for access to writing and books.
Video description

Will Larson is the chief technology officer at Carta. Prior to joining Carta, he was the CTO at Calm and held engineering leadership roles at Stripe, Uber, and Digg. He is the author of two foundational engineering career books, An Elegant Puzzle and Staff Engineer, and The Engineering Executive’s Primer, which will be released in February of next year. In our conversation, we discuss: • Systems thinking: what it is and how to apply it • Advice for product managers on fostering productive relationships with engineering managers • Why companies should treat engineers like adults • How to best measure developer productivity • Writing and its impact on his career • How to balance writing with a demanding job • How to develop your company values — Brought to you by DX—A platform for measuring and improving developer productivity: https://getdx.com/lenny | OneSchema—Import CSV data 10x faster: https://oneschema.co/lenny | Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Find the transcript and references at: https://www.lennysnewsletter.com/p/the-engineering-mindset-will-larson Where to find Will Larson: • X: https://twitter.com/Lethain • LinkedIn: https://www.linkedin.com/in/will-larson-a44b543/ • Website: https://lethain.com/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Will’s background (04:12) Changes in the field of engineering (06:27) We need to stop treating engineers like children (08:32) Systems thinking (13:23) Implementing systems thinking in hiring (16:32) Engineering strategy (20:21) Examples of engineering strategies (25:08) How to get good at strategy (26:48) The importance of writing about things that excite you (32:40) The biggest risk to content creation is quitting too soon (35:24) How to make time for writing (37:41) Tips for aspiring writers (41:18) Building productive relationships between product managers and engineers (43:45) Giving the same performance rating to EMs and PMs (48:24) Measuring engineering productivity (55:53) Defining company values (01:02:10) Failure corner: the Digg rewrite (01:11:05) Will’s upcoming book, The Engineering Executive’s Primer (01:12:04) Lightning round Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.