Engineering Org Design
Team structure, platform teams, management models, and how CTOs design orgs that ship.
Episodes
S2E39
Understanding The Fear: Adaptive Leadership in the AI Age
Brad & Scott
Brad & Scott discuss growing fear about AI among engineers and managers, framing it as an "adaptive moment" requiring leaders to disrupt old stabilizing practices. They explore concerns that AI lowers the barrier for others to change systems, increasing accountability, on-call risk, and architectural drift—problems that existed pre-AI but are now intensified.
Engineering Org Design
S1E37
Deploys, Demos, and the Elusive Metric of Engineering Productivity
Brad & Scott
Brad & Scott wrestle with one of the industry's toughest questions: How do you measure engineering productivity? The conversation explores the hypothesis that deploy frequency per person can serve as a practical proxy for velocity, and the cultural tradeoffs this metric may introduce.
Engineering Org Design
S1E27
The Outsourcing Playbook Gets an AI Rewrite: Engineering in the Age of AI and Global Teams
Brad & Scott
Brad & Scott dig deep into the real-world lessons of managing outsourced and distributed engineering teams. Drawing on decades of experience with partners in Romania, India, Syria, and Ukraine, they unpack what makes these relationships thrive, or fail.
Engineering Org Design
S1E26
From Code to Careers: AI's Disruption of Software and Work Itself
Brad & Scott
Brad & Scott dive into the fast-evolving world of generative AI—and what it means for the future of software development, careers, and the economy at large. They unpack how tools like GPT-4o and Claude are shifting the very nature of programming work, boosting productivity while raising deeper questions about the future of white-collar jobs.
Engineering Org Design
S1E25
How GenAI Is Changing the Two Guys in a Garage Founder Story
with Justin Wolf & Joe Malek
Brad & Scott welcome tech entrepreneurs and avid scuba divers Justin Wolf and Joe Malek to share the story behind their generative AI–powered scuba guidebook and community app. What started as a side project became a test case for building fast with LLMs and pushing the boundaries of what small, technical founding teams can accomplish.
Engineering Org Design
S1E24
Autonomous Engineering Teams: What Works, What Breaks
Brad & Scott
Brad & Scott unpack one of the most debated questions in engineering leadership: Should engineering managers also serve as tech leads? They explore the organizational signals that indicate whether a team is ready to thrive with true cross-functional autonomy, and what can go wrong when roles and responsibilities blur.
Engineering Org Design
S1E22
From Chicken to Chatbots: Generative AI in Hospitality with Justin Kaufman
with Justin Kaufman, Mount Joy
Brad & Scott interview special guest Justin Kaufman . Justin discusses his unique journey from working in health tech to founding the Mount Joy restaurant, where he's implemented innovative tech solutions to enhance customer engagement.
Engineering Org Design
S1E21
Fake Profiles, Real Disruption: What AI Is (and Isn't) Doing to Tech Recruiting with Dave Hardwick
with Dave Hardwick
Brad & Scott discuss with Dave Hardwick, the disruptive yet beneficial impact of AI on recruitment processes. They explore how AI tools are revolutionizing candidate searches for recruiters, but also touch upon the challenge of encountering fake profiles.
Engineering Org Design
S1E20
Beyond the Resume: How to Hire and Get Hired in Tech with Dave Hardwick
with Dave Hardwick
Brad & Scott welcome Dave Hardwick, a seasoned technical recruiter. Together, they explore the intricacies of recruiting engineering talent, the gaps between what CTOs think they want and what they actually hire, and the importance of clear job descriptions and scorecards in the hiring process.
Engineering Org Design
S1E19
Bonus Episode with Greg Conklin: Navigating Hyper-growth and Tech Debt at Groupon and Dropbox
with Greg Conklin
Brad & Scott dive into a conversation with Greg Conklin, exploring his experiences at two hypergrowth companies, Groupon and Dropbox. Greg shares insights on the unique cultural and technical strategies employed at both organizations during their rapid expansion phases.
Engineering Org Design
S1E18
Culture, Quality, and Tech Debt: Lessons from the Front Lines with Greg Conklin
with Greg Conklin
Brad & Scott are joined by special guest Greg Conklin for a candid and insightful conversation on what it takes to build high-performing engineering teams. Drawing from their shared time at the telemedicine startup 98point6, the trio unpacks hard-earned lessons around tech debt, operational excellence, and culture-first leadership .
Engineering Org Design
S1E17
Lessons from the Mountains: Retrospectives and the Secret Sauce of High Performance Teams
Brad & Scott
Brad & Scott explore the art and impact of retrospectives in engineering teams. Drawing on their experiences in both software and high-stakes environments like mountain rescue, they discuss the value of retrospectives for continuous improvement, building trust, and uncovering root causes of both successes and failures.
Engineering Org Design
S1E15
Understanding and Managing Technical Debt: Insights from John Helm
with John Helm
Brad & Scott welcome guest John Helm to discuss the complexities and ramifications of technical debt within software projects. The conversation explores various analogies, including financial bonds and naked calls, to explain the impact of technical debt on project timelines and functionality.
Engineering Org Design
S1E14
The Ball of Mud - Tackling Software Monoliths and Decomposing Tech Debt: Strategies and Challenges
Brad & Scott
Brad & Scott discuss the intricate challenges of engineering leadership, focusing on the decomposition of monolithic software systems and the monumental task of managing tech debt. They delve into the practical strategies for breaking down monoliths, the complexity of interdependencies and 'God objects,' and debate the merits of incremental rewrites versus complete overhauls.
Engineering Org Design
S1E13
Embracing Failure and Innovation: Lessons from Punk Rock with Kevin Goldsmith
with Kevin Goldsmith
Brad & Scott are joined by Kevin Goldsmith, a seasoned tech leader with a background in both music and technology. Kevin shares insights from his early career in the music industry, his journey through various tech roles, and his book 'It Depends'.
Engineering Org Design
S1E12
Navigating Technical Debt and Code Quality in Agile Teams
Brad & Scott
Brad & Scott discuss a recent incident in a small engineering team that highlights challenges of managing technical debt even with skilled developers and robust code review processes. They explore the importance of refactoring in agile methodologies, the pitfalls of large pull requests, and the complexities of quantifying and prioritizing technical debt.
Engineering Org Design
S1E11
The Reality of AI in Software Engineering and the Future of Work
Brad & Scott
Brad & Scott discuss a recent OpenAI study on AI's effectiveness in completing real-world freelance software engineering tasks. They delve into the results showing that AI models completed only 26% of tasks successfully, highlighting current limitations.
Engineering Org Design
S1E10
Tackling Tech Culture and Interviewing: Insights from Ted Neward
with Ted Neward
Brad & Scott welcome special guest Ted Neward, a senior distinguished engineer at Capital One, joins the hosts to discuss the challenges and intricacies of engineering leadership and technology culture. Ted shares his diverse experiences, from his previous roles at Rocket Mortgage and Smartsheet to his current position.
Engineering Org Design
Articles
How can businesses measure the impact of addressing technical debt?
How can companies effectively learn from both failures and successes?
How can companies effectively manage time zone differences with global engineering teams?
How can companies improve their technical interview processes to better assess candidates' skills?
How can engineering leaders coach their teams through AI-related fears in the workplace?
How can engineering leaders effectively manage technical debt in a startup environment?
How can engineering teams effectively measure productivity beyond traditional metrics?
How can retrospectives improve decision-making in high-stakes environments?
How can teams effectively evaluate and prioritize technical debt?
How did Groupon and Dropbox handle hyper-growth differently?
How do different Generative AI tools compare in app development?
How does Generative AI impact the speed and cost of developing a niche app?
How does organizational structure impact engineering team performance?
How effective is AI in completing real-world freelance software engineering tasks?
How is AI transforming the tools used by tech recruiters?
What are the challenges and strategies for decomposing a software monolith?
What are the key elements to include in a resume for a software engineering role?
What are the key factors for successful autonomous engineering teams?
What are the potential pitfalls of using deploy frequency as a productivity metric?
What challenges do fake profiles pose in tech recruiting?
What is the fundamental definition of technical debt according to John Helm?
What role does company culture play in the success of engineering teams?
What role does tech culture play in transforming a company from a traditional business to a tech-focused organization?
What strategies did Groupon use to manage technical debt during its rapid expansion?