The (big) picture of debt

Technical debt comes with context - understanding the circumstances and history that led to current problems is crucial before attempting solutions

Meet teams where they are - rather than forcing radical changes, provide incremental paths and tools that work with their current reality

Build trust through action - demonstrate willingness to do the hard work yourself before asking others to change

Ensure proper timing - tackle technical debt when:

• The organization feels the pain
• Teams have capacity and motivation
• Infrastructure and tooling is mature enough
• Multiple stakeholders’ incentives align

Find partners and champions - significant technical transformations require:

• Dedicated teams for ongoing maintenance
• Engineers willing to lead long-term
• Stakeholders across different areas
• Shared ownership and accountability

Make changes incrementally:

• Start small with willing early adopters
• Automate what’s possible
• Allow for safe rollbacks
• Build confidence through small wins

Focus on self-service and automation:

• Provide frameworks and tools
• Build in best practices
• Make the “right way” the easy way
• Reduce friction for adoption

Be ready to let go:

• Hand off projects to dedicated owners
• Allow others to champion the cause
• Accept that timing may not be right
• Focus efforts where organization shows readiness