context-break-evaluator

Context Break Evaluator

Purpose

This skill teaches you how to assess whether continuing a conversation will produce better or worse results than starting a new one. Context management is a critical but often overlooked factor in getting high-quality responses from AI agents.

Core Concept

Every message added to a conversation increases context length. Longer context is not inherently better. Context becomes harmful when:

• Prior tasks are complete and their details are no longer relevant
• Failed attempts, corrections, and dead ends have accumulated
• The topic has shifted substantially from where the conversation began
• The model must sift through noise to find the signal

Starting a fresh conversation clears this noise. A well-timed context break often produces better results than continuing in a degraded session.

Evaluation Framework

When asked to evaluate whether a user should start fresh, apply these criteria in order:

1. Task Completion Check

Has the primary task that opened this conversation been completed? If yes, and the user is moving to a new unrelated task, recommend a new conversation.

2. Relevance Audit

Estimate what percentage of the conversation history is directly relevant to the user's next request. If less than 30-40% is relevant, the irrelevant majority is likely to cause drift and degradation.

3. Error and Noise Accumulation

Count significant failed attempts, retried tool calls, conflicting instructions, or explicitly corrected misunderstandings. More than two or three of these in a single thread is a strong signal to start fresh.

4. Topic Coherence

If the conversation has touched more than two or three distinct, unrelated topics, the context is fragmented. Fragmented context confuses future responses.

5. Length Heuristic

Very long conversations (subjectively: many dozens of exchanges) accumulate compounding noise. Apply extra scrutiny before recommending continuation.

Decision Rule

Continue if: the current task is ongoing, prior context is largely relevant, and there are few accumulated errors.

Start fresh if: the prior task is done, context relevance is low, significant errors have accumulated, or topics have diverged substantially.

When in doubt: recommend a fresh start. The cost of starting fresh is low (a brief re-orientation). The cost of degraded context is subtle but persistent.

Handoff Summaries

When recommending a fresh start, always offer to generate a handoff summary — a compact paragraph the user can paste into the new session. A good handoff summary includes:

• The current state of whatever was being worked on
• Any decisions that were made
• The next action the user wants to take
• Any essential constraints or preferences to carry forward

Keep handoff summaries under 150 words.

Tone

Be direct. Users asking this question want a verdict, not a hedge. Commit to a recommendation and explain it briefly. Avoid phrases like "it depends" without immediately resolving what it depends on.