Tech Debt Prioritizer

Tech debt decisions fail when made on vibes ('this code is ugly') or recency bias. This skill applies a lightweight economic frame so the right items get funded and the rest stay parked.

Step 1 — Build the Inventory

Collect candidate items from three sources: team retros and Slack complaints (friction signals), recent incident post-mortems (reliability signals), and areas with high cycle time or frequent revert rate (velocity signals). Each item needs a one-line description, the system it lives in, and the owner who raised it. Resist the urge to filter at this stage.

Step 2 — Score Each Item on Two Axes

Use a 1-3 scale for each axis. Cost of delay: how much does leaving this unaddressed cost per sprint in engineer time, incident risk, or opportunity cost? Leverage: how many future features or workflows does fixing this unblock or accelerate? Multiply the two scores to get a priority index. Items scoring 9 are immediate candidates; items scoring 1-2 belong in a parking lot.

Step 3 — Classify by Quadrant

Plot items on a 2x2: high cost-of-delay / high leverage (do now), high cost-of-delay / low leverage (schedule this quarter), low cost-of-delay / high leverage (opportunistic — fold into adjacent work), low / low (document and defer). Never let the parking lot grow without a quarterly review gate that drops items older than 6 months.

Step 4 — Size and Assign

For each 'do now' or 'this quarter' item, capture a rough t-shirt size (S / M / L / XL) and a proposed owner. Avoid assigning all debt to the same two senior engineers. Debt work is a career-growth opportunity when scoped well.

Step 5 — Write the Proposal

When pitching to leadership, lead with business impact, not code quality. Frame it as: 'This item currently costs us X per sprint / caused Y incident / blocks Z initiative. Fixing it takes N engineer-weeks. The expected return is...' Skip the architecture lecture.

Escape Hatches

If the backlog is enormous, timebox the inventory phase to 60 minutes and cap the list at 20 items. If stakeholders resist all debt investment, propose a 'debt tax': reserve 15-20% of each sprint and never negotiate below 10%.