Engineering Leadership Self-Assessment Checklist : Chapter IV

Level 1, The Observer

Goal: Build awareness of how engineering actually works in your projects/programs.

Awareness & Exposure

• I attended at least one architecture/design review this month.
• I shadowed an engineer during deployment, incident triage, or feature build.
• I mapped part of the tech stack and documented owners, dependencies, and pain points.
• I reviewed recent postmortems and identified at least one recurring issue.

Reflection

• I can explain the architecture in plain language.
• I can describe the top 2–3 engineering pain points without relying on others.
• I noticed where silent firefighting is happening.

Milestone: I understand how engineering gets done, not just what gets done.

Level 2, The Questioner

Goal: Influence quality of thinking without dictating solutions.

Quality Questions

• I asked scaling questions (“What if traffic doubles?”).
• I asked maintainability questions (“Can a new engineer pick this up?”).
• I asked people questions (““What new skill or concept are you picking up through this work?””).
• I introduced/reinforced a lightweight design review checklist.

Culture & Engagement

• I created a safe space for healthy debate during planning.
• I observed how teams justified decisions and tradeoffs.
• I noticed whether tech debt was logged or ignored.

Milestone: Engineers see me as a thoughtful reviewer, not just a delivery tracker.

Level 3, The Enabler

Goal: Create space and systems for better engineering decisions.

Systems & Sustainability

• I reserved time in plans for refactoring/tech debt reduction.
• I pushed for documentation or onboarding improvements.
• I encouraged or hosted an internal tech talk or knowledge share.
• I mentored at least one senior IC toward leadership.

Observation

• I noticed if teams felt less rushed in delivery.
• I observed whether tech debt is now visible and shrinking.
• I saw knowledge spreading beyond single individuals.

Milestone: The system around me encourages good engineering, without constant intervention.

Level 4, The Technical Partner

Goal: Become a trusted co-pilot in engineering strategy.

Strategic Involvement

• I co-created or reviewed a long-term technical roadmap.
• I connected at least one tech requirement to a clear business outcome.
• I advocated for meaningful metrics (e.g., reliability, performance, dev experience).
• I participated in incident reviews or architecture boards as an equal voice.

Trust Signals

• Product/PMs sought my input on technical feasibility.
• Engineers proactively involved me in complex design discussions.
• I was able to demo a Technical POC credibly to large audience and senior leadership.

Milestone: I shape technical direction as a peer partner, not just a facilitator.

Level 5, The Engineering Leader

Goal: Lead through technical vision, culture, and strategy.

Vision & Culture

• I communicated a clear technical vision aligned with business goals.
• I championed a culture of learning, experimentation, and innovation.
• I supported career growth paths for senior engineers/architects.
• I made conscious tradeoffs balancing speed vs sustainability.
• I reviewed org design/ownership boundaries/platform strategy.

Impact

• Engineering quality is embedded into my leadership DNA.
• Teams deliver faster because of the foundations we have built.
• I have become a magnet for talent and people want to work with me.

Milestone: “I have shifted from delivery manager to true engineering leader, building both software and the culture to scale it.”

How to Use This Checklist

• Review monthly.
• Tick off items honestly, partial progress is fine.
• Journal 2–3 reflections: What did I learn? What’s my growth edge?
• Share highlights with a mentor or trusted peer for accountability.
• Revisit past levels, leadership is not strictly linear.

This is not a detailed check list, it is just a sample template to start with. We can make it as elaborate, as we want.

Closing Thoughts

Shifting from delivery management to true engineering leadership is not about throwing away what you already do well. It is about widening the lens.

If you are a delivery manager today, you already have the discipline, coordination skills, and people focus to succeed. What is left is curiosity, technical empathy, and the courage to ask: “Are we building the right thing, in the right way, for the long run?”

Leadership at its best is not just about getting work done, it is about building teams, systems, and cultures that continue to thrive long after the deadlines are forgotten.

The path is not quick, but it is worth it. Because great engineering leaders don’t just deliver features. They deliver futures.