- Ali Ismail
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- OSS Violation
Embarrassing Game Over
You’re behind the wheel of a Ferrari, engine purring at the starting line. The light turns green, and with steady confidence, you take action: clutch down, a perfect rev, shift, release…
-STALL-
Whoops, you jumped straight to 2nd gear instead of starting in 1st. The car sputters embarrassingly, and the race is over before it even begins. GAME OVER.
OSS Domains
The Leveling Ladder is not just a sequence of individual career promotions, but instead it’s a natural progression within three interdependent domains. As you progress in your career, you’ll be required to seamlessly transition between these different gears depending on the context.
Operations: Mastering the basics, delivering projects, and meeting immediate goals.
Systems: Scaling your work, managing complexity, and solving problems across teams.
Strategy: Thinking long-term, aligning with business goals, and driving the future.
Each step builds on the previous one, and catastrophic failures are due to skipping a step or a poor foundation in a previous one. There’s countless cautionary tales of business skipping these steps.
Case Study: TSB Bank Migration Failure
In 2018, TSB leadership was aggressively pushing for a system migration to save costs and increase their independence. They failed to validate data, properly test, and completely lacked rollback mechanisms.
They moved from operations (everyday tasks) to strategy (cost savings) without investing in systems (integration testing, risk management, and coordination).
This resulted in millions of customers losing access to their accounts, and the company incurring £330 million in damages.
Mapping the Phases to Leveling Ladder
Let’s map the OSS domains to the Leveling Ladder and take a closer look on how it affects software engineers and their careers.
Phase 1: Operations (L3-L5)
Most engineers live here. The skill sets all end up building towards delivering projects. Starting out you may do minor bug fixes. With some mastery on the ecosystem you can push out features and own them. By mastering pushing features you can get good at delivering projects rapidly.
Focus: Mastering tasks and delivering projects.
Responsibilities:
Deliver features, fix bugs, and meet deadlines.
Collaborate within the team to ensure project success.
Begin to connect your work to the bigger picture.
Skills Required:
Coding, debugging, testing.
Communication and time management.
Growth Challenges:
Narrow focus on individual tasks.
Limited exposure to cross-team dependencies.
How to Excel:
Communicate progress and blockers clearly.
Deliver high-quality, maintainable code.
Start observing how your work impacts the team and the system.
Phase 2: Systems (L6-L7)
When engineers transition here, their typically still involved in code but have an added layer of solving scalable problems. This includes designing architectures, managing bottlenecks, and that existing systems interface seamlessly. The lens shifts from being project focused to balancing complexities across teams, systems, and business priorities. At this level, you are relied upon for driving technical execution and alignment across the organization.
Focus: Scaling and managing complexity.
Responsibilities:
Design system architecture and handle cross-team dependencies.
Balance short-term firefighting with long-term planning.
Identify and solve bottlenecks.
Skills Required:
Systems thinking and dependency management.
Cross-functional collaboration and trade-off analysis.
Growth Challenges:
Managing competing priorities and overwhelming complexity.
Aligning systems with business goals.
How to Excel:
Look for patterns in problems across teams.
Propose scalable solutions with clear trade-offs.
Mentor others to strengthen team-wide capabilities.
Phase 3: Strategy (L8-L9)
This level is all about raising the standards to the industry level. And if you’re already caught up to the industry level, it’s about raising the industry’s standards. When you’re at this level, you’re thinking years ahead. You’re balancing innovation with stability, and ensuring your systems scale with company growth. Mastery here means driving the vision that shapes the company’s future while empowering teams to execute sustainably.
Do note, that this mindset can be applied to the top of Operations and Systems. In Operations it would be all about raising the codebase quality to meet or exceed industry best practices (e.g., clean code, automated testing, efficient debugging). And at Systems it would be in terms of pushing for meeting or exceeding industry best practice in terms of team-wide improvements in velocity, communication, and collaboration during project execution.
Focus: Driving vision and ensuring long-term sustainability.
Responsibilities:
Align technical vision with business goals.
Address tech debt and ensure systems scale with growth.
Prioritize innovation without sacrificing stability.
Skills Required:
Business acumen and risk management.
Expertise in balancing short- and long-term goals.
Growth Challenges:
Misalignment between technical and business priorities.
Balancing innovation with operational stability.
How to Excel:
Build frameworks for scalable decision-making.
Regularly audit systems for scalability and sustainability.
Communicate clearly with executives and stakeholders.
Beyond the Ladder
Smoothly shifting between Operations, Systems, and Strategy requires expanding your perspective. Each phase challenges your mindset in different ways. You need to master delivering quality code rapidly, managing business needs cross functionally, and driving vision to stay ahead for years to come.
In order to excel you need to find time to reflect, adapt, and raise your standards. This applies to refining code, systems, or redefining how things should be done. Your depth of understanding is your leverage in the game. The secret is to know the context of where you are and juxtaposing it against where you need to be.
Push yourself to master each of these disciplines.