Technical Debt Assessment Skill

When to Use This Skill

Use this skill when:

• Tech Debt Assessment tasks - Working on technical debt identification, quantification, and prioritization for informed remediation planning
• Planning or design - Need guidance on Tech Debt Assessment approaches
• Best practices - Want to follow established patterns and standards

Overview

Systematic identification, quantification, and prioritization of technical debt to enable informed decisions about remediation investments.

MANDATORY: Documentation-First Approach

Before providing tech debt guidance:

1. Invoke docs-management skill for code quality documentation
2. Verify current practices via MCP servers (perplexity for latest debt frameworks)
3. Base all guidance on established methodologies

Technical Debt Quadrant (Fowler)

Debt Classification

                    Deliberate
                        │
          ┌─────────────┼─────────────┐
          │             │             │
          │  Prudent/   │  Reckless/  │
          │  Deliberate │  Deliberate │
          │             │             │
          │ "We know    │ "We don't   │
          │ the trade-  │ have time   │
          │ offs"       │ for design" │
Prudent ──┼─────────────┼─────────────┼── Reckless
          │             │             │
          │  Prudent/   │  Reckless/  │
          │ Inadvertent │ Inadvertent │
          │             │             │
          │ "Now we     │ "What's     │
          │ know how    │ layering?"  │
          │ to do it"   │             │
          └─────────────┼─────────────┘
                        │
                   Inadvertent

Debt Types

public enum DebtQuadrant
{
    PrudentDeliberate,   // Conscious trade-off for business reasons
    PrudentInadvertent,  // Learned better approach after implementation
    RecklessDeliberate,  // Cut corners knowingly
    RecklessInadvertent  // Don't know good practices
}

public enum DebtCategory
{
    // Code Level
    CodeSmells,          // Duplications, long methods, dead code
    TestingDebt,         // Missing tests, flaky tests, slow tests
    DocumentationDebt,   // Missing/outdated docs, tribal knowledge

    // Design Level
    DesignDebt,          // Violated principles, poor abstractions
    DependencyDebt,      // Outdated libraries, version conflicts
    ConfigurationDebt,   // Hardcoded values, environment coupling

    // Architecture Level
    ArchitectureDebt,    // Violated boundaries, coupling, scalability limits
    InfrastructureDebt,  // Manual processes, poor CI/CD, missing monitoring
    SecurityDebt         // Known vulnerabilities, outdated practices
}

public sealed record TechnicalDebtItem(
    string Id,
    string Title,
    string Description,
    DebtCategory Category,
    DebtQuadrant Quadrant,
    string Location,          // File(s), module, service
    DebtSeverity Severity,
    DebtQuantification Quantification,
    DebtImpact Impact,
    string Origin,            // When/how debt was introduced
    DateOnly IdentifiedDate,
    string IdentifiedBy,
    DebtStatus Status);

public enum DebtSeverity
{
    Low,       // Minor inconvenience
    Medium,    // Noticeable slowdown
    High,      // Significant impediment
    Critical   // Blocking development
}

public enum DebtStatus
{
    Identified,
    Analyzed,
    Prioritized,
    Scheduled,
    InProgress,
    Resolved,
    Accepted    // Deliberately not addressing
}

Debt Quantification

Principal and Interest Model

public sealed record DebtQuantification(
    decimal Principal,        // Cost to fix now (hours or $)
    decimal InterestRate,     // Additional cost per time period (%)
    TimeSpan PaymentPeriod,   // How often interest compounds
    decimal AccruedInterest,  // Interest already accumulated
    decimal TotalOwed,        // Principal + Accrued Interest
    DateOnly BreakEvenDate);  // When fixing pays for itself

public sealed class DebtCalculator
{
    /// <summary>
    /// Calculate when paying off debt becomes worthwhile
    /// </summary>
    public DebtQuantification Quantify(
        decimal fixCostHours,
        decimal hourlyRate,
        decimal weeklyInterestHours,
        int weeksAccrued)
    {
        var principal = fixCostHours * hourlyRate;
        var weeklyInterest = weeklyInterestHours * hourlyRate;
        var interestRate = weeklyInterest / principal;
        var accruedInterest = weeklyInterest * weeksAccrued;
        var totalOwed = principal + accruedInterest;

        // Break even when cumulative interest > principal
        var weeksToBreakEven = (int)Math.Ceiling(principal / weeklyInterest);

        return new DebtQuantification(
            Principal: principal,
            InterestRate: interestRate,
            PaymentPeriod: TimeSpan.FromDays(7),
            AccruedInterest: accruedInterest,
            TotalOwed: totalOwed,
            BreakEvenDate: DateOnly.FromDateTime(DateTime.UtcNow.AddDays(weeksToBreakEven * 7)));
    }
}

Interest Calculation Examples

public static class DebtInterestExamples
{
    /// <summary>
    /// Missing unit tests: extra debugging time per bug
    /// </summary>
    public static DebtQuantification MissingTestsDebt(
        int untestedMethods,
        decimal debuggingHoursPerBug,
        decimal bugsPerMonth,
        decimal testWritingHoursPerMethod)
    {
        var principal = untestedMethods * testWritingHoursPerMethod;
        var monthlyInterest = debuggingHoursPerBug * bugsPerMonth;

        return new DebtQuantification(
            Principal: principal,
            InterestRate: monthlyInterest / principal,
            PaymentPeriod: TimeSpan.FromDays(30),
            AccruedInterest: 0,
            TotalOwed: principal,
            BreakEvenDate: DateOnly.FromDateTime(DateTime.UtcNow.AddMonths(
                (int)Math.Ceiling(principal / monthlyInterest))));
    }

    /// <summary>
    /// Legacy framework: time spent on workarounds
    /// </summary>
    public static DebtQuantification LegacyFrameworkDebt(
        decimal migrationCostHours,
        decimal weeklyWorkaroundHours)
    {
        return new DebtQuantification(
            Principal: migrationCostHours,
            InterestRate: weeklyWorkaroundHours / migrationCostHours,
            PaymentPeriod: TimeSpan.FromDays(7),
            AccruedInterest: 0,
            TotalOwed: migrationCostHours,
            BreakEvenDate: DateOnly.FromDateTime(DateTime.UtcNow.AddDays(
                (int)Math.Ceiling(migrationCostHours / weeklyWorkaroundHours) * 7)));
    }
}

Debt Identification

Static Analysis Integration

public sealed class DebtIdentifier
{
    public async Task<IReadOnlyList<TechnicalDebtItem>> IdentifyFromAnalysis(
        string projectPath)
    {
        var debts = new List<TechnicalDebtItem>();

        // Code quality tools
        debts.AddRange(await RunSonarQube(projectPath));
        debts.AddRange(await RunCodeClimate(projectPath));

        // Dependency analysis
        debts.AddRange(await AnalyzeDependencies(projectPath));

        // Test coverage gaps
        debts.AddRange(await AnalyzeTestCoverage(projectPath));

        // Documentation analysis
        debts.AddRange(await AnalyzeDocumentation(projectPath));

        // Architecture conformance
        debts.AddRange(await CheckArchitectureRules(projectPath));

        return debts;
    }

    private async Task<IEnumerable<TechnicalDebtItem>> AnalyzeDependencies(
        string projectPath)
    {
        // Check for outdated packages
        // dotnet list package --outdated
        // npm outdated

        var outdated = await GetOutdatedPackages(projectPath);

        return outdated.Select(pkg => new TechnicalDebtItem(
            Id: $"DEP-{pkg.Name}",
            Title: $"Outdated: {pkg.Name}",
            Description: $"Package {pkg.Name} is {pkg.VersionsBehind} versions behind. Current: {pkg.CurrentVersion}, Latest: {pkg.LatestVersion}",
            Category: DebtCategory.DependencyDebt,
            Quadrant: DebtQuadrant.PrudentInadvertent,
            Location: pkg.ProjectFile,
            Severity: pkg.HasSecurityIssues ? DebtSeverity.Critical : DebtSeverity.Medium,
            Quantification: EstimateUpgradeEffort(pkg),
            Impact: AssessDependencyImpact(pkg),
            Origin: "Dependency became outdated over time",
            IdentifiedDate: DateOnly.FromDateTime(DateTime.UtcNow),
            IdentifiedBy: "Automated scan",
            Status: DebtStatus.Identified));
    }
}

Common Debt Patterns

public static class CommonDebtPatterns
{
    public static IEnumerable<DebtPattern> GetPatterns()
    {
        yield return new DebtPattern(
            Name: "God Class",
            Category: DebtCategory.DesignDebt,
            Indicators: new[] { "Class > 500 lines", "Class has > 20 methods", "Low cohesion" },
            TypicalPrincipal: "8-40 hours to refactor",
            TypicalInterest: "1-2 hours/week in confusion and merge conflicts");

        yield return new DebtPattern(
            Name: "Duplicated Code",
            Category: DebtCategory.CodeSmells,
            Indicators: new[] { "Copy-paste violations", "Similar logic in multiple places" },
            TypicalPrincipal: "1-4 hours per duplication",
            TypicalInterest: "0.5-1 hours per change (must update multiple places)");

        yield return new DebtPattern(
            Name: "Missing Tests",
            Category: DebtCategory.TestingDebt,
            Indicators: new[] { "Low code coverage", "Fear of refactoring", "Bugs in production" },
            TypicalPrincipal: "0.5-2 hours per method",
            TypicalInterest: "2-4 hours per bug in debugging");

        yield return new DebtPattern(
            Name: "Hardcoded Configuration",
            Category: DebtCategory.ConfigurationDebt,
            Indicators: new[] { "Magic strings", "Environment-specific values in code" },
            TypicalPrincipal: "0.5-1 hour per instance",
            TypicalInterest: "Deployment failures, environment issues");

        yield return new DebtPattern(
            Name: "Outdated Documentation",
            Category: DebtCategory.DocumentationDebt,
            Indicators: new[] { "Docs don't match code", "Tribal knowledge", "Onboarding issues" },
            TypicalPrincipal: "4-8 hours per component",
            TypicalInterest: "1-2 hours per new team member onboarding");

        yield return new DebtPattern(
            Name: "Monolithic Architecture",
            Category: DebtCategory.ArchitectureDebt,
            Indicators: new[] { "Tight coupling", "Deployment bottleneck", "Can't scale independently" },
            TypicalPrincipal: "Months of refactoring",
            TypicalInterest: "Slower releases, harder scaling");
    }
}

Debt Impact Assessment

Impact Model

public sealed record DebtImpact(
    DeveloperProductivityImpact Productivity,
    QualityImpact Quality,
    VelocityImpact Velocity,
    MoraleImpact Morale,
    BusinessImpact Business);

public sealed record DeveloperProductivityImpact(
    int AffectedDevelopers,
    decimal HoursLostPerWeek,
    string Description);

public sealed record QualityImpact(
    int AdditionalBugsPerMonth,
    bool IncreasesSecurityRisk,
    bool ReducesReliability,
    string Description);

public sealed record VelocityImpact(
    decimal DeliverySlowdownPercent,
    bool BlocksNewFeatures,
    int FeaturesBlocked,
    string Description);

public sealed record MoraleImpact(
    bool CausesFrustration,
    bool ContributesToBurnout,
    bool AffectsRetention,
    string Description);

public sealed record BusinessImpact(
    decimal RevenueLossPerMonth,
    decimal CustomerChurnRisk,
    bool AffectsCompliance,
    string Description);

Impact Scoring

public sealed class ImpactScorer
{
    public int CalculateImpactScore(DebtImpact impact)
    {
        var score = 0;

        // Productivity (0-25 points)
        score += Math.Min(25, impact.Productivity.AffectedDevelopers *
            (int)impact.Productivity.HoursLostPerWeek);

        // Quality (0-25 points)
        score += impact.Quality.IncreasesSecurityRisk ? 15 : 0;
        score += impact.Quality.ReducesReliability ? 10 : 0;

        // Velocity (0-25 points)
        score += impact.Velocity.BlocksNewFeatures ? 20 : 0;
        score += Math.Min(5, impact.Velocity.FeaturesBlocked);

        // Business (0-25 points)
        score += impact.Business.AffectsCompliance ? 25 : 0;
        score += impact.Business.CustomerChurnRisk > 0.1m ? 15 : 0;

        return Math.Min(100, score);
    }
}

Debt Prioritization

Prioritization Matrix

public sealed class DebtPrioritizer
{
    public IReadOnlyList<TechnicalDebtItem> Prioritize(
        IEnumerable<TechnicalDebtItem> debts)
    {
        return debts
            .Select(d => (Debt: d, Score: CalculatePriorityScore(d)))
            .OrderByDescending(x => x.Score)
            .Select(x => x.Debt)
            .ToList();
    }

    private double CalculatePriorityScore(TechnicalDebtItem debt)
    {
        // Weighted scoring
        var impactScore = CalculateImpactScore(debt.Impact) * 0.4;
        var effortScore = (100 - CalculateEffortScore(debt.Quantification.Principal)) * 0.2;
        var interestScore = CalculateInterestScore(debt.Quantification) * 0.3;
        var ageScore = CalculateAgeScore(debt.IdentifiedDate) * 0.1;

        return impactScore + effortScore + interestScore + ageScore;
    }

    private double CalculateInterestScore(DebtQuantification quantification)
    {
        // Higher interest rate = higher priority
        return Math.Min(100, (double)quantification.InterestRate * 1000);
    }

    private double CalculateAgeScore(DateOnly identifiedDate)
    {
        // Older debt gets slightly higher priority (avoid perpetual deferral)
        var age = DateOnly.FromDateTime(DateTime.UtcNow).DayNumber - identifiedDate.DayNumber;
        return Math.Min(100, age / 3.65); // Max score at 1 year old
    }
}

Cost of Delay Prioritization

public sealed class CostOfDelayPrioritizer
{
    /// <summary>
    /// CD3: Cost of Delay Divided by Duration
    /// Higher values = higher priority
    /// </summary>
    public double CalculateCD3(TechnicalDebtItem debt)
    {
        // Cost of Delay = Weekly interest being paid
        var weeklyInterest = debt.Quantification.InterestRate *
            debt.Quantification.Principal;

        // Duration = Time to fix (in weeks)
        var durationWeeks = (double)debt.Quantification.Principal / 40; // 40 hour weeks

        return (double)weeklyInterest / durationWeeks;
    }

    public IReadOnlyList<TechnicalDebtItem> PrioritizeByCD3(
        IEnumerable<TechnicalDebtItem> debts)
    {
        return debts
            .Select(d => (Debt: d, CD3: CalculateCD3(d)))
            .OrderByDescending(x => x.CD3)
            .Select(x => x.Debt)
            .ToList();
    }
}

Remediation Planning

Remediation Strategies

public enum RemediationStrategy
{
    PayOff,          // Fix completely
    Refinance,       // Reduce interest without full fix
    Consolidate,     // Combine multiple debts into one fix
    Accept,          // Acknowledge and don't fix
    Strangler,       // Gradually replace
    ScheduledPayment // Fix incrementally over time
}

public sealed record RemediationPlan(
    IReadOnlyList<TechnicalDebtItem> Debts,
    RemediationStrategy Strategy,
    TimeSpan EstimatedDuration,
    decimal EstimatedEffort,
    IReadOnlyList<string> Prerequisites,
    IReadOnlyList<string> Risks,
    IReadOnlyList<Milestone> Milestones);

public sealed class RemediationPlanner
{
    public RemediationStrategy RecommendStrategy(TechnicalDebtItem debt)
    {
        // High interest + low principal = Pay off
        if (debt.Quantification.InterestRate > 0.1m &&
            debt.Quantification.Principal < 40)
            return RemediationStrategy.PayOff;

        // Very high principal = Strangler or scheduled
        if (debt.Quantification.Principal > 200)
            return debt.Category == DebtCategory.ArchitectureDebt
                ? RemediationStrategy.Strangler
                : RemediationStrategy.ScheduledPayment;

        // Low interest = Consider accepting
        if (debt.Quantification.InterestRate < 0.01m)
            return RemediationStrategy.Accept;

        // Multiple related debts = Consolidate
        // (would need to analyze relationships)

        return RemediationStrategy.PayOff;
    }
}

Debt Tracking

Debt Register

public sealed class TechnicalDebtRegister
{
    private readonly List<TechnicalDebtItem> _debts = new();

    public DebtSummary GetSummary()
    {
        var openDebts = _debts.Where(d => d.Status != DebtStatus.Resolved).ToList();

        return new DebtSummary(
            TotalDebtItems: openDebts.Count,
            TotalPrincipal: openDebts.Sum(d => d.Quantification.Principal),
            TotalAccruedInterest: openDebts.Sum(d => d.Quantification.AccruedInterest),
            WeeklyInterestPayment: openDebts.Sum(d =>
                d.Quantification.Principal * d.Quantification.InterestRate),
            ByCategory: openDebts
                .GroupBy(d => d.Category)
                .ToDictionary(g => g.Key, g => g.Count()),
            BySeverity: openDebts
                .GroupBy(d => d.Severity)
                .ToDictionary(g => g.Key, g => g.Count()),
            TopDebtors: openDebts
                .OrderByDescending(d => d.Quantification.TotalOwed)
                .Take(10)
                .ToList());
    }

    public DebtTrend GetTrend(int months = 12)
    {
        // Track debt over time
        var monthlySnapshots = GetMonthlySnapshots(months);

        return new DebtTrend(
            Snapshots: monthlySnapshots,
            IsIncreasing: monthlySnapshots.Last().TotalDebt > monthlySnapshots.First().TotalDebt,
            AverageMonthlyChange: CalculateAverageChange(monthlySnapshots));
    }
}

Workflow

When assessing technical debt:

1. Identify: Use static analysis, code review, team input
2. Categorize: Classify by type and quadrant
3. Quantify: Estimate principal and interest
4. Impact Assess: Evaluate productivity, quality, velocity impacts
5. Prioritize: Rank by CD3 or weighted scoring
6. Plan Remediation: Choose strategy and create plan
7. Track: Monitor debt levels over time
8. Report: Communicate debt status to stakeholders

References

For detailed templates:

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Last Updated: 2025-12-26