long-running-work-planning

name	long-running-work-planning
description	Use this skill when facing complex problems requiring multi-step reasoning, architectural decisions, debugging with unclear root causes, or tasks where the problem scope is uncertain. Invoke even if the user doesn't explicitly mention "reasoning" or "thinking through" — triggers on phrases like "figure out why", "analyze this", "what's the best approach", or when initial attempts fail.
license	MIT
allowed-tools	mcp__sequentialthinking__sequentialthinking

Long-Running Work Planning

Maintain work continuity across extended tasks. Break down ambiguous problems, explore alternatives, and prevent timeout errors by working in structured increments.

Strategy Selection

Choose your continuity strategy based on available tooling:

Agent Starts Complex Task
    │
    ▼
Sequential-Thinking MCP Available?
    ├─ Yes → Use MCP for Structured Reasoning
    │         │
    │         ▼
    │     To-Do Tools Available?
    │         ├─ Yes → ⭐ Combine: MCP + To-Do (Recommended)
    │         └─ No  → Use MCP Alone
    │
    └─ No → To-Do Tools Available?
              ├─ Yes → Use To-Do for Task Decomposition
              └─ No  → Use Manual Chunking Strategy

Strategy 1: Sequential-Thinking MCP (Primary)

Use when the MCP server is configured. Provides structured reasoning with revision and branching support.

mcp__sequentialthinking__sequentialthinking({
  thought: "First, I need to understand what's causing the intermittent failure...",
  thoughtNumber: 1,
  totalThoughts: 5,
  nextThoughtNeeded: true
})

Strategy 2: To-Do Tools (Secondary)

Use when MCP is not available but built-in to-do tools are. Break tasks into visible, trackable steps.

Pattern:

1. Create a to-do list with all identified steps
2. Mark tasks as in-progress when starting
3. Mark tasks as complete after verification
4. Maintain visible progress throughout

Best for:

• Task decomposition with clear steps
• Work that benefits from visible progress tracking
• Environments where users want to see incremental progress

Strategy 3: Manual Chunking (Fallback)

Use when neither MCP nor to-do tools are available.

Pattern:

1. Identify the total scope of work
2. Break into 3-5 step chunks
3. Output each chunk with a clear progress marker
4. Summarize before moving to next chunk

Example:

[Progress 1/3] Analyzing the problem scope...
<output analysis>

[Progress 2/3] Evaluating potential solutions...
<output evaluation>

[Progress 3/3] Recommending approach...
<output recommendation>

Strategy 4: Combined MCP + To-Do (Recommended)

Use both together for maximum effectiveness:

• Sequential-thinking MCP: Provides structured reasoning, revision tracking, and branching
• To-do tools: Provides visible progress tracking for the user

Pattern:

1. Use to-do to create a visible task breakdown
2. Use sequential-thinking MCP for complex reasoning within each task
3. Update to-do status as reasoning progresses
4. Emit intermediate results to prevent timeout

Per-Phase Todo Lists: When running a spec-driven phase skill that defines its own Per-Phase Todo List section, use that phase-scoped list instead of creating a generic one. The per-phase list takes precedence over this generic strategy.

When to Use

Trigger Pattern	Example
Problem scope unclear	"Something's wrong with the API but I'm not sure what"
Multi-step reasoning required	"Help me design a caching strategy"
Root cause unknown	"This bug only happens under load"
Multiple valid approaches	"Should I use PostgreSQL or MongoDB for this?"
Initial attempt failed	"I tried fixing it but it's still broken"
Architectural decisions	"How should I structure the microservices?"
Complex debugging	"The race condition is hard to reproduce"
Long-running tasks	"Write a technical design for this feature"

When to SKIP

Do NOT use this skill for:

Skip Pattern	Why
Simple lookups	"What's the capital of France?"
Known solutions	"Add error handling to this function"
Formatting tasks	"Convert this JSON to YAML"
Single-step edits	"Rename this variable"
Factual queries	"What does git rebase do?"
Trivial calculations	"Sum these numbers"
Straightforward implementations	"Create a login form with these fields"

Timeout Prevention

Threshold Indicators

Watch for these signs that you're approaching timeout risk:

Indicator	Risk Level	Action
Estimated steps > 10	High	Chunk immediately, use MCP or to-do
Complex multi-file changes	High	Break into phases, output incrementally
Ambiguous requirements	Medium	Clarify first, then chunk
No clear end state	Medium	Define success criteria, then chunk
New domain/concept	Medium	Research phase, then chunk

Proactive Chunking

Before starting complex work:

1. Estimate scope: How many distinct steps? How many files affected?
2. Check thresholds: If steps > 10 or files > 5, chunk first
3. Choose strategy: MCP preferred, to-do secondary, manual fallback
4. Output plan: Share the chunking plan before diving in

Incremental Output Patterns

Pattern A: Phase-Based Output

## Phase 1: Analysis
<output analysis results>

## Phase 2: Design
<output design decisions>

## Phase 3: Implementation Plan
<output task breakdown>

Pattern B: Progress Markers

[1/5] Setting up the foundation...
[2/5] Building core components...
[3/5] Adding integrations...
[4/5] Testing and validation...
[5/5] Documentation and cleanup...

Pattern C: Checkpoint-Based

Checkpoint: Requirements understood
<output>

Checkpoint: Design approach selected
<output>

Checkpoint: Implementation complete
<output>

Anti-Pattern: Holding Output

❌ Bad: Working through 15 steps internally, then outputting everything at once ✅ Good: Outputting after every 2-3 steps with progress markers

MCP Tool Reference

Sequential-Thinking MCP Parameters

Parameter	Required	Description
thought	Yes	Current reasoning step
thoughtNumber	Yes	Current step number (1-indexed)
totalThoughts	Yes	Estimated total steps needed
nextThoughtNeeded	Yes	true if more steps needed
isRevision	No	Mark as revision of previous thought
revisesThought	No	Which thought number is being revised
branchFromThought	No	Branch point thought number
branchId	No	Identifier for the branch
needsMoreThoughts	No	Request more thoughts than estimated

Core Patterns

Linear Progression

Standard step-by-step reasoning:

{ "thought": "Analyze the error stack trace...", "thoughtNumber": 1, "totalThoughts": 4, "nextThoughtNeeded": true }
{ "thought": "Identify the failing component...", "thoughtNumber": 2, "totalThoughts": 4, "nextThoughtNeeded": true }
{ "thought": "Trace the data flow...", "thoughtNumber": 3, "totalThoughts": 4, "nextThoughtNeeded": true }
{ "thought": "Root cause is X, fix is Y"       

Revision

Correct previous reasoning:

{ "thought": "Wait, my assumption in thought 2 was wrong...", "thoughtNumber": 3, "totalThoughts": 5, "nextThoughtNeeded": true, "isRevision": true, "revisesThought": 2 }

Branching

Explore alternatives:

{ "thought": "Alternative approach: what if we use async/await instead?", "thoughtNumber": 4, "totalThoughts": 6, "nextThoughtNeeded": true, "branchFromThought": 3, "branchId": "async-approach" }

Timeout Prevention with MCP

1. Start conservative: Estimate totalThoughts at 3-5 for most problems. Extend with needsMoreThoughts: true if needed.

2. Chunk reasoning: If approaching 10+ thoughts, summarize findings and restart the sequence.

3. Dynamic adjustment: Set nextThoughtNeeded: false early if the answer becomes clear.

4. Avoid overthinking: If 3 consecutive thoughts don't add value, conclude.

Examples

Example: Complex Debugging (USE tool)

User: "My API works locally but fails in production sporadically"

Thought 1: "List differences between local and production environments..."
Thought 2: "Check for race conditions in shared state..."
Thought 3: "Investigate timeout configurations..."
Thought 4: "Production has different load balancer settings causing session affinity issues"

Example: Long Design Task (USE tool + to-do)

User: "Design the architecture for a new payment system"

To-do list created (or use the Per-Phase Todo List from the active spec-driven skill):

1. Gather requirements
2. Design data models
3. Design API contracts
4. Design integration points
5. Document decisions

If a spec-driven phase skill (e.g., spec-driven-technical-designer) is active, its Per-Phase Todo List takes precedence and should be used instead of this generic breakdown.

Then use MCP for each phase of reasoning.

Example: Simple Task (SKIP tool)

User: "Add a README file to this project"

Direct response. No structured reasoning needed — straightforward single-step task.

Reference

For detailed decision frameworks and advanced patterns, see references/decision-framework.md.