In this episode of Engineering Evolved, Tom Barber discusses the pitfalls of over-engineering platform infrastructure, particularly for mid-sized companies. He shares insights from his experience at NASA's Jet Propulsion Laboratory, emphasizing the importance of right-sizing infrastructure to match team needs and capacity. The episode covers the build versus buy framework, the challenges of internal tooling, and the significance of documentation and automation in maintaining efficient operations.
Summary
In this conversation, Tom Barber discusses the challenges organizations face when dealing with legacy systems and the importance of recognizing the human element in system migration. He emphasizes that migration is not just a technical project but a transition that impacts people's identities and roles within the organization.
Takeaways
Summary
In this episode of Engineering Evolved, Tom Barber discusses the critical first 90 days of a modernization initiative for engineering directors. He emphasizes that success is not solely about technology but about understanding the business pain, building trust, and navigating organizational dynamics. The episode provides a week-by-week action plan, highlighting the importance of quick wins, effective communication, and avoiding common pitfalls in modernization efforts.
Takeaways
Summary
In this conversation, Tom Barber discusses the challenges of managing feature requests and the importance of strategic deployment to enhance team efficiency. He emphasizes the need to prioritize time-consuming tasks to free up valuable hours for the team, ultimately leading to increased productivity without additional hiring costs.
Takeaways
Summary
In this episode of Engineering Evolved, Tom Barber discusses the critical aspects of cloud migration, emphasizing that many migrations fail due to poor planning and execution. He contrasts successful migrations, like Netflix's, with failures like TSB Bank's, highlighting the importance of treating migration as a product launch. Barber introduces the Strangler Fig pattern as a preferred migration strategy, outlines the six Rs of cloud migration, and stresses the need for effective communication and monitoring during the process. He also provides rollback strategies and discusses the importance of chaos engineering in ensuring resilience against outages. The episode concludes with key principles for successful cloud migration, urging listeners to prioritize discipline over speed.
Takeaways
Summary
In this conversation, Tom Barber discusses the significant impact of technical debt on American companies, highlighting that it costs them $1.5 trillion annually. He emphasizes that many executives are unaware of this issue, which often remains hidden within organizations, particularly in engineering payroll. Barber explains how technical debt can lead to lost deals and increased risk exposure, likening it to a ticking time bomb that can have severe consequences when it detonates.
Takeaways
Summary
Most midsize companies are making terrible architecture decisions because they're copying Netflix instead of solving their actual problems. This episode cuts through the hype and gives you a practical framework for deciding when you need microservices, when you don't, and everything in between. We talk about why "microservices" is a terrible name that encourages bad decisions, the five factors that should actually drive your architecture choices, and the spectrum of options between monolith and distributed systems that nobody tells you about. Plus, specific signals that tell you when it's actually time to evolve.
In This Episode:
Episode Summary
Are your "cross-functional" teams actually just a feature factory in disguise? In this solo deep-dive, I break down the real differences between truly empowered teams and organizations that just reorganized the boxes on an org chart. You'll learn how to measure true cross-functionality, spot the warning signs you're still running a feature factory, and get concrete strategies to transform your teams.
What You'll Learn
The Real Definition of Feature Factory – It's not about org structure; it's about how decisions get made and what gets measured
Five Capabilities That Define True Cross-Functionality:
Eight Red Flags You're Still Running a Feature Factory:
Three Frameworks to Measure Cross-Functionality:
Six Transformation Strategies That Actually Work:
Most engineering leaders would fail miserably as product managers. They'd get fired for shipping features nobody wants, ignoring user feedback, and measuring the wrong things. But here's the thing - your engineering team IS a product. And the techniques you use to build great products are exactly what you need to build a great engineering organization.
In this episode, I break down the Product Thinking Framework: a radically different approach to engineering leadership that will change how you think about your team forever.
In This Episode:
Key Takeaways:
1. Set up Engineering Office Hours
2. Shadow your engineers quarterly
3. Cut infrastructure projects into MVP experiments
4. Measure outcomes, not outputs
5. Iterate constantly on your team
Nobody wakes up wanting to be a modernization director. In this deeply personal episode, I share my journey from writing simple code at NASA JPL to leading complex system transformations at a fintech startup—and the expensive failures that taught me everything about modernization leadership.
You'll hear the story of two catastrophic failures: turning atmospheric science research code into a production web portal, and failures with month end reporting systems as a junior developer. They taught me lessons that no certification or consultant ever could.
If you've ever had a "works on my machine" moment turn into a deployment disaster, this episode is for you.
Key Topics Covered
Key Takeaways
Lesson 1: Always Think About the Future State
Before writing a single line of code, ask: Where will this actually run? Who will maintain it? What happens when things fail? The gap between "works in dev" and "works in production" gets baked in at the architecture stage, not discovered at deployment.
Lesson 2: You Can't Deploy Something Impossibly Hard to Maintain
Elegant architecture means nothing if the team who has to run it can't understand, debug, or update it. Build for the maintainers, not for the architects. Meeting requirements includes sustainability.
Lesson 3: Empower Developers to Test and Embrace Failure
The best modernization teams fail early, fail small, fail visibly, and learn fast. Create realistic test environments. Give permission to break things. Make failure a learning opportunity, not a career-limiting move.
Lesson 4: Know When You're Going Down the Wrong Path—and Admit It
The worst thing in modernization is forcing a bad approach because you're too proud to pivot. Recognize the signs: projects that keep slipping, workarounds that multiply, excuses about the environment. Have the courage to stop, reassess, and choose a different path.
Sometimes the right answer is the simpler tool that works everywhere, not the sophisticated tool that requires expertise to deploy.
Why Mid-Sized Companies Are Stuck (And How to Break Free)
You've achieved product-market fit. You're generating real revenue. You have 200-1000 employees and a tech team of 20-150 engineers. You're not a startup anymore—but you're also not Google.
And you're stuck in hell.
The VP of Engineering reads all the right blogs, follows all the thought leaders, and decides to implement microservices like Netflix. Six months later, deployments take longer, bugs multiply, engineers threaten to quit, and leadership is asking why you just spent half a million dollars to make things worse.
This isn't incompetence. This is the reality of being in the missing middle—too big for startup playbooks, too small for enterprise frameworks.
In this episode, host Tom Barber breaks down:
Stop trying to copy Spotify. Stop implementing frameworks designed for 10,000 employees. Start building systems that match your actual reality.
Perfect for: CTOs, VPs of Engineering, and technical leaders at mid-sized companies who are tired of advice that doesn't fit their world.