Soft Skills Engineering · Jamison Dance and Dave Smith

Episode 458: Infinite tech debt hack and figuring out what is going on

·34 min·3 clips

Dave reveals why paying technical debt is like rolling a D20 minus 15—often making things worse.

This episode of Soft Skills Engineering features hosts Dave Smith and Jameson Dance answering listener questions about workplace challenges in software development. The hosts provide practical advice on navigating non-technical aspects of engineering roles, drawing from their own industry experiences. The first question comes from Nico, a developer stressed by teammates whose technical debt refactoring consistently creates more debt and merge conflicts. Dave and Jameson compare paying down such debt to rolling a D20 die with a negative modifier, where attempts often worsen the situation. They suggest that refactors promising to delete entire services or thousands of lines of code are more reliably beneficial than those merely rearranging abstractions. The hosts advise Nico to quantify the cost of resolving merge conflicts as lost business time. They propose discussing ways to avoid breaking work-in-progress, perhaps by implementing file locks or synchronization points. Jameson notes that high-energy developers might be channeled toward tangibly beneficial projects like reducing hosting costs. He also highlights the real cost of inconsistency when new patterns are added without removing old ones. Dave offers a counterpoint that the questioner might be resistant to changes that are net positive. A second question comes from an anonymous engineer at a big tech company who feels siloed and lost regarding team priorities and customer needs. The hosts agree that managers generally appreciate when engineers seek broader context. Dave recounts the difficulty of discovering information in a large organization, where org charts and dependency maps are often nonexistent. He describes the challenge of finding knowledgeable colleagues who understand inter-team relationships. Jameson recommends directly asking internal customer teams about their work or consulting team wikis. They note the common existence of multiple, often outdated, internal wiki systems. The hosts strongly advise using one-on-one meetings with managers to ask about priorities and customer goals. They explain that demonstrating this curiosity can change a manager's perception and open doors for career advancement. Dave emphasizes that understanding current priorities allows an engineer to effectively argue for new ideas by ranking them against existing goals. A memorable insight is that paying technical debt can function like a Dungeons & Dragons roll with a high chance of making the debt worse. The episode humorously explores the cultural artifact of corporate wikis, noting they range from well-maintained to "post-apocalyptic wastelands." One host recalls a team that embedded employee badge photos on their wiki as a mark of pride. They discuss the inherent challenge of keeping wiki search results relevant at scale. A surprising claim is that in a large enough organization, the number of wiki instances always exceeds what you know about. The hosts conclude that wikis are a necessary scaling tool to avoid being overwhelmed by inbound inquiries from other teams. The tone is conversational, humorous, and anecdotal, with the hosts riffing on extended metaphors. The style is advice-oriented, blending personal experience with practical, actionable suggestions. This episode would appeal to software engineers struggling with team dynamics, refactoring pitfalls, or navigating large corporate structures. Listeners seeking highly technical, code-deep dives might find the focus on soft skills and organizational commentary less engaging.

As heard by us

Tech debt gets easier to manage when change is handled like a shared, backward-compatible migration.

Soft Skills Engineering treats tech debt as a shared team problem rather than a solo cleanup chore. The episode keeps its focus on the real friction: surprise refactors, shifting permissions, and code changes that can block someone else from moving forward.

Read the full review in PlayNext →

Why you'd press play

If tech debt keeps breaking your week, this one speaks your language.

Read the full recommendation in PlayNext →

Listen to the show on

Apple Podcasts Spotify

Play clips from this episode More from Soft Skills Engineering