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Technical debt is inevitable, but how engineers and teams manage it determines whether it becomes a controlled investment or a painful burden. Often I was told technical debt is about "Pay me now, or pay me later, the choice is yours." And, I often chose to pay it later (either by force or due to other priorities). Here lately, I have come across many posts from some talented software engineers frustrated that a system they built many years ago was being criticized by newer engineers without any curiosity about the original decisions made. Their frustration is valid—every system is built within specific constraints, and it’s easy to judge past work with today’s knowledge. But this raises an important question: Are we designing software with enough foresight to minimize the pain of evolution?
Past Work Wasn’t “Wrong”—But Was It Designed for Change?
Engineers can benefit from assuming that past developers were competent and made decisions based on the best information available at the time. However, every system will eventually age, and some will do so more gracefully than others. The key is not just making the best decision for "right now" but also designing with adaptability in mind.
Design vs. Conversations: Was There a Plan for Change?
Prior to implementation, most engineers will consult experts, their leaders, and architects prior to building and refining the system, but what about:
- A design review process that accounted for future shifts?
- Were there any scalability and maintainability assessments?
- A decision log explaining why specific choices were made?
Great engineering isn’t just about solving today’s problems—it’s about anticipating the unknown. While we can’t predict everything, structured design reviews and documentation can help future engineers understand the decisions made.
The Role of Engineering Leaders in Guiding Technical Decisions
Technical design reviews are often seen as tedious, but they pay dividends in the long run. Unfortunately, many engineering leaders and managers either don’t prioritize them or lack the technical discernment to guide their teams effectively. And I get it. It is daunting. Visualizing the solution is huge. It can be done iteratively. This isn’t about blame—it’s about empowering leaders to create a culture of foresight and resilience.
How can leaders step up?
- Dedicate time for structured technical reviews. Even if schedules are tight, investing in foresight saves time and effort down the line. Creating templates for this helps. Another question to ask: Does this design align with the outcomes we expect the solution to provide now and in the future? And for how long?
- Foster collaboration between engineers and decision-makers. Ensure that technical and business goals align without sacrificing long-term maintainability.
- Encourage a mindset of adaptability. Leaders can foster an environment where engineers view design reviews as a valuable learning tool rather than a bureaucratic hurdle.
A strong leadership presence ensures that technical debt is managed intentionally rather than becoming an afterthought. By guiding engineers in making informed, future-ready decisions, leaders can prevent unnecessary rework and create systems that stand the test of time. There may still be technical debt, but the impact can be reduced.
Criticism vs. Curiosity: How to Give (and Receive) Feedback on Legacy Code
- New engineers: Instead of assuming past work was flawed, ask questions like “What constraints shaped this design?” instead of “This was built wrong.”
- Experienced engineers: Instead of feeling defensive, acknowledge that all systems evolve. The best engineers view feedback as an opportunity to refine future work.
- Leaders and managers: Encourage a culture of constructive inquiry. Critique can be a valuable opportunity for learning rather than focusing on blame.
Coaching Engineers to Build with Longevity in Mind
- Normalize technical debt and system evolution. It’s part of the software lifecycle.
- Encourage documentation—not just for how things work, but why decisions were made.
- Train engineers to embrace critique as part of growth, not as a personal attack.
Conclusion: The Future Will Judge Your Work—And That’s Okay
Being okay with the future judging your work may not feel 'okay' in the moment. I get it. But, inevitably your work will be outdated too. The best engineers don’t just code for the present—they set up the future team for success. By designing systems with flexibility/scalability/operational efficiency in mind, fostering curiosity over criticism, and ensuring teams document key decisions, we can reduce frustration and build software that evolves with time. The real question isn’t whether a system will need to change—it’s whether we are preparing for that change in a way that helps, rather than hinders, future teams. I hope engineering leaders and managers see this as an opportunity for growth rather than a reason to villainize, condemn, or shame engineers. Encouraging a culture of learning and adaptability will create stronger, more resilient teams that thrive even as technology evolves.