A few different sets of ideas clustered together to help assess the priority:
Trade-off analysis:
Feature Group | Competitive Offering | Overall Product Health (performance, security, efficiency) | Long Term Risk | Scoring |
Customer-facing | Yes (3) | No (1) | Risk of losing user engagement (5) | 9 |
Tech debt/architectural | Doesn't impact (1) | Yes (5) | Scalability & vulnerability issues (5) | 11 |
Categorize tech debts in terms of value to the business & measure it in terms of the effort for the work:
Category | Effort | Value |
App Performance | Medium | Doesn't yield any significant change |
Security Update | Low | Allows user-profiles secure |
Android OS changes (compliance) | High | App/Feature Crash, App updates |
Inhibits certain modal/design toolkit changes | Medium | Allow creating modern modal design & in-app experience |
Based on the first analysis, we get a score that tells us that tech debt will be expensive misses and should be prioritized.
Based on the second analysis, I can choose categories of work I want to do incrementally towards tech features so I don't completely neglect the most important ones.
Lastly, I would ask questions about what the "functional feature is and see how it impacts user engagement". I will try to map how the feature of that feature may be tied to one of these categories from the second analysis and try to find a meaningful co-relation (if one exists). Having a more digestible picture of the scenario then will help us decided what efforts to prioritize.