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tree-of-thoughts

@bnadlerjr/dotfiles
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Branching reasoning that explores multiple solution paths simultaneously with evaluation and backtracking. Use for strategic planning, puzzles, design decisions, brainstorming alternatives, or any problem where the first approach may not be optimal. Triggers on "explore options", "compare approaches", "what are the alternatives", or problems requiring lookahead.

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SKILL.md

name tree-of-thoughts
description Branching reasoning that explores multiple solution paths simultaneously with evaluation and backtracking. Use for strategic planning, puzzles, design decisions, brainstorming alternatives, or any problem where the first approach may not be optimal. Triggers on "explore options", "compare approaches", "what are the alternatives", or problems requiring lookahead.

Tree of Thoughts (ToT)

Explores multiple reasoning paths as a tree, evaluating candidates and backtracking from dead ends.

Core Mechanism

At each reasoning step:

  1. Generate: Produce multiple candidate thoughts/approaches
  2. Evaluate: Assess each candidate (promising / uncertain / dead-end)
  3. Search: Pursue promising paths, abandon dead ends, backtrack when stuck

Process

1. Frame the problem and identify the decision space
2. Generate 2-4 distinct initial approaches
3. For each approach, evaluate:
   - Feasibility: Can this work given constraints?
   - Progress: Does this move toward the goal?
   - Reversibility: Can we recover if wrong?
4. Expand the most promising path(s)
5. If stuck, backtrack to last branch point and try alternative
6. Continue until solution or all paths exhausted

Evaluation Heuristics

Rate each candidate thought:

  • Sure (pursue): Clear progress, no obvious blockers
  • Maybe (explore cautiously): Potential but uncertain
  • Impossible (abandon): Violates constraints or leads nowhere

When to Apply

  • Problems where >60% of failures occur at the first step (puzzles, planning)
  • Design decisions with multiple valid approaches
  • Brainstorming where diverse options are valuable
  • Tasks requiring strategic lookahead (games, negotiations)

Three Experts Pattern

Imagine three experts with different perspectives approaching this problem:

Expert A (prioritizes simplicity): [approach + reasoning]
Expert B (prioritizes performance): [approach + reasoning]  
Expert C (prioritizes extensibility): [approach + reasoning]

Each expert evaluates their approach:
- What are the key trade-offs?
- What could go wrong?
- [If fatal flaw discovered, expert acknowledges and withdraws]

Synthesis: Which approach (or hybrid) best fits the constraints?

Search Strategies

  • BFS: When solution depth is unknown, explore breadth first
  • DFS: When deep exploration is needed before switching paths
  • Best-first: When evaluation function reliably ranks candidates

Anti-Patterns

  • Using for simple sequential problems (CoT is simpler)
  • Generating too many branches (3-4 is usually optimal)
  • Failing to actually backtrack when paths fail
  • Shallow evaluation that doesn't catch fatal flaws early