Winning with Observability: Part 2

Kyle SheltonKyle Shelton
6 min read

Winning with Observability: Part 2 - Scaling, Modernization, and Maturity

In Part 1, we explored how observability transforms culture and accelerates delivery. Now, in Part 2, we tackle scaling complex systems, navigating migrations, and building a mature observability practice to drive success.

Scaling: Conquering Complexity

Modern systems are intricate, but scaling them effectively requires understanding the difference between complication and complexity. Complication arises from poorly designed systems with tangled dependencies, creating unnecessary hurdles. Complexity, however, is inherent in distributed systems—microservices, hybrid clouds, and interconnected components naturally produce unpredictable interactions. In distributed environments, complexity matters because failures cascade across services, obscure root causes, and amplify downtime. #bad.

Here are the core scaling challenges:

  • System complexity: Dynamic interactions in distributed systems make it hard to predict behavior or diagnose issues.

  • Ineffective scaling: The old mantra of "just throw hardware at it" fails in microservice environments. Adding servers doesn’t address bottlenecks in distributed architectures, wastes resources, and increases environmental impact through higher energy consumption.

  • Inconsistent environments: Disparities across dev, test, and prod setups lead to unpredictable performance and errors.

  • Communication silos: In large organizations, teams working in isolation lack shared context, slowing resolution and innovation.

  • High toil: Manual, repetitive tasks drain engineering time and morale, diverting focus from high-value work.

Solutions Through SRE, DevOps, and Platform Engineering

To scale effectively, adopt practices rooted in Site Reliability Engineering (SRE), DevOps, and platform engineering:

  • Proactive performance management: Define Service Level Objectives (SLOs) to set clear performance targets. Monitor them to catch issues before they escalate.

  • Streamlined incident response: Use observability to pinpoint issues fast, reducing downtime and customer impact.

  • Break silos: Foster collaboration with shared dashboards and real-time data, aligning teams on system health.

  • Eliminate toil: Automate repetitive tasks to free engineers for high-value work, reducing "muda" (waste).

These practices turn chaotic systems into manageable, scalable ones.

Migration and Modernization: Navigating the Chaos

Migrations, acquisitions, and modernization efforts amplify complexity. Whether integrating acquired systems or retiring legacy infrastructure, teams face steep challenges. In my career at a telecom startup, we moved our entire operation from on-premises servers in Allen, Texas, to AWS cloud. This shift forced my role to pivot from network engineering to cloud architecture, highlighting the real-world stakes of modernization.

Here are the core challenges:

  • Tool sprawl: Disparate tools without standardization fragment visibility. During the telecom migration, we juggled multiple monitoring systems, each showing partial truths.

  • Legacy systems: Technical debt from outdated infrastructure slows progress and obscures behavior. Our old network hardware couldn’t match AWS’s scalability.

  • Data migration issues: Incompatible formats and integration failures disrupt operations. Moving customer data to the cloud hit snags due to inconsistent schemas.

  • Cultural clashes: Merging teams with different workflows hinders collaboration. The shift to cloud required retraining network engineers, causing friction.

  • Loss of visibility: Transitions obscure system context. Without clear telemetry, diagnosing issues during our cloud migration felt like guesswork.

  • Talent retention: Modernization often outpaces talent. Maintaining skilled engineers during our telecom’s cloud pivot was tough—modern stacks like AWS demand new skills, and legacy expertise can feel obsolete.

Modern stacks typically win in head-to-head comparisons. Cloud-native solutions offer scalability, flexibility, and resilience that legacy systems struggle to match. But transitions are painful without the right tools.

Observability as the Anchor

Observability brings clarity to chaotic migrations and disperate systems:

  • Single pane of glass: Unified dashboards consolidate metrics, logs, and traces across old and new systems. For our AWS migration, a centralized view would have revealed issues across on-prem and cloud environments.

  • Validate success: Real-time monitoring confirms migrations meet performance and reliability goals. Post-migration, we could have verified service uptime with clear SLOs.

  • Accelerate troubleshooting: Correlated data speeds up issue resolution. During our cloud transition, observability could have pinpointed latency spikes faster.

  • Foster collaboration: Shared tools bridge cultural gaps. Observability dashboards helped our network and cloud teams align, easing knowledge transfer.

With observability, migrations shift from chaotic fire drills to structured, predictable processes. It’s the anchor that keeps teams grounded, even when talent and technology are in flux.

The Ideal State: Observability Maturity

Troubleshooting in distributed systems is hard. Applications span clouds, on-premises servers, and hybrid setups. Failures cascade unexpectedly, data lives in silos, and telemetry lacks standardization. Noise from overloaded data and complex systems buries critical signals.

The 4 Ws of Observability

Effective troubleshooting hinges on answering four questions, even without deep system knowledge:

  1. What happened? Identify the issue—e.g., a service failure or latency spike.

  2. When did it happen? Pinpoint the exact timing to trace back to triggers.

  3. Where did it happen? Locate the affected component in the system.

  4. Why did it happen? Uncover root causes through correlated data.

Answering these questions quickly—across high-level overviews and low-level details—empowers teams to resolve issues efficiently.

The Ideal State: Observability Maturity

Troubleshooting in distributed systems is hard. Applications span clouds, on-premises servers, and hybrid setups. Failures cascade unexpectedly, data lives in silos, and telemetry lacks standardization. Noise from overloaded data and complex systems buries critical signals.

The 4 Ws of Observability

Effective troubleshooting hinges on answering four questions, even without deep system knowledge:

  1. What happened? Identify the issue—e.g., a service failure or latency spike.

  2. When did it happen? Pinpoint the exact timing to trace back to triggers.

  3. Where did it happen? Locate the affected component in the system.

  4. Why did it happen? Uncover root causes through correlated data.

Answering these questions quickly—across high-level overviews and low-level details—empowers teams to resolve issues efficiently.

Observability Value: Strategic Vs Tactical

Observability delivers value across two dimensions: tactical and strategic. Tactical actions drive immediate impact, while strategic initiatives build long-term resilience. Together, they create a mature observability practice that scales with complexity.

Observability Value QuadrantTactical- Bailing WaterStrategic- Paddling the Boat
FocusImmediate impact: Fix issues, restore service, improve system reliability.Long-term resilience: Standardize practices, upskill teams, drive adoption.
Key Actions- Collect metrics, logs, traces, and profiles for full system visibility.

- Build intuitive dashboards for real-time insights.
- Automate incident response and self-healing systems.
- Optimize MTTX (Mean Time to Detect, Identify, and Resolve). | - Define observability policies to ensure consistent telemetry standards.
- Invest in enablement and training to upskill teams across the organization.
- Establish a Center of Excellence (CoE) to champion observability adoption. | | Outcome | Faster issue resolution, reduced downtime, and improved customer experience. | Unified observability culture, scalable systems, and proactive problem prevention. |

This quadrant illustrates how tactical wins—like real-time dashboards and automated healing—complement strategic efforts, such as standardized policies and team enablement. A mature observability practice balances both, enabling teams to troubleshoot efficiently and build systems that prevent issues before they arise.

Conclusion: Transform with Observability

Observability is a game-changer. It empowers teams to scale complex systems, navigate migrations, and achieve a mature, resilient state. By fostering collaboration, reducing toil, and providing clarity, observability drives operational excellence.

Assess your observability maturity today. Adopt SLOs, break down silos, and leverage tools like Grafana cloud to build a proactive, data-driven culture. The payoff? Faster delivery, happier teams, and delighted customers.

Let’s connect on observability, SRE, or shared passions—reach out on linkedin. Thanks for reading, and here’s to winning with observability!How

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Written by

Kyle Shelton
Kyle Shelton

Outdoorsman | Networking | SRE | Chaos & Platform Engineering | DevOps @toyotaracing | former @aws @splunk @verizon @gm | Thoughts are my own Personal: Husband | GirldadX3 | BBQ | Outdoors | Nascar | Baseball | Triathlons