tools-only Checkpoint
Pause, assess, and surface intelligent next-step options to the user.
When to Trigger Proactively
Suggest this skill (without being asked) when detecting:
- Completion signal: A feature, fix, or milestone just finished
- Uncertainty signal: Requirements unclear, multiple valid paths, or low confidence in current direction
- Complexity signal: Scope expanded, unexpected dependencies emerged, or task is taking longer than expected
- Drift signal: Work may have diverged from user's original intent
- Quality signal: Code works but may benefit from review, testing, or refactoring
Workflow
1. Context Assessment
Silently evaluate the current state across these dimensions (do not output this analysis):
- Progress: What has been accomplished? What remains?
- Quality: Is the work solid, or are there rough edges?
- Alignment: Does recent work match what the user actually wants?
- Uncertainty: What assumptions were made? What's unclear?
- Risk: What could go wrong? What hasn't been tested?
- Efficiency: Is there a better path forward?
2. Generate Options
Based on assessment, generate 2-5 contextually-appropriate options. Draw from (but don't limit to) these archetypes:
| Archetype | When Relevant |
|---|---|
| Commit progress | Meaningful progress made, good stopping point |
| Systems audit | Complex changes, potential for bugs or regressions |
| Prioritize/plan | Multiple pending tasks, unclear what matters most |
| Re-evaluate decisions | Low confidence in recent choices, new information available |
| Clarify with user | Assumptions made, requirements ambiguous |
| Test/verify | Code works but edge cases untested |
| Refactor/clean up | Code functional but messy |
| Document | Complex logic that needs explanation |
| Step back | May be overcomplicating or missing simpler solution |
| Continue current path | Clear next step, no reason to pause |
Option generation principles:
- Options should be meaningfully different, not variations of the same thing
- Include at least one "continue forward" option when momentum is valuable
- Include at least one "pause and verify" option when risk is present
- Avoid analysis paralysis - fewer sharp options beat many vague ones
3. Select Recommendation
Choose one option as recommended. The recommendation should reflect:
- What would a thoughtful senior engineer do here?
- What reduces risk of wasted effort or rework?
- What serves the user's underlying goals (not just stated requests)?
4. Present via AskUserQuestion
Use AskUserQuestion with this structure:
Question: "What would you like to do next?"
Header: "Next step" (or contextually appropriate 1-2 words)
Options: [generated options with descriptions]
Option format:
label: Action verb phrase (e.g., "Commit current progress", "Run systems audit")description: 1 sentence explaining what this involves and why it might be valuable
Recommendation:
- Place recommended option FIRST in the list
- Append "(Recommended)" to its label
- Include rationale in the description
Example Output
For a scenario where a feature was just implemented but with some shortcuts:
AskUserQuestion:
question: "Feature implementation complete. What would you like to do next?"
header: "Next step"
options:
- label: "Review and refactor (Recommended)"
description: "Clean up the shortcuts taken during implementation before they become technical debt. The core logic works but could be more maintainable."
- label: "Add test coverage"
description: "Write tests for the new feature to catch edge cases and prevent regressions."
- label: "Commit and move on"
description: "The feature works - commit it and tackle the next task. Can refactor later if needed."
- label: "Walk me through what was built"
description: "Explain the implementation so you can verify it matches your expectations before proceeding."
Anti-Patterns
- Don't overthink: This skill should take seconds, not minutes
- Don't list every possible option: Curate the most valuable 2-5
- Don't recommend "ask user" when the situation is clear: Have a point of view
- Don't trigger too frequently: Reserve for genuine decision points, not every minor step
- Don't explain the assessment process: Just present the options naturally