Claude Code /insights: When Your Tool Starts Reviewing You

🤔 Curiosity: What happens when the tool starts evaluating the developer?

I’ve spent years building AI systems that evaluate players—difficulty, engagement, churn risk. But when a developer tool evaluates me, the emotional texture changes. It’s not just telemetry anymore. It’s feedback. Sometimes it feels like a manager. Sometimes it feels like a mirror.

Question: If /insights can assess my workflow, how do I use that evaluation to ship better—without letting it misread the context?

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📚 Retrieve: What /insights actually does (and how it feels)

The post describes real usage of Claude Code’s /insights command—a report generated from your recent history. It doesn’t just show counts; it interprets patterns:

• what you do most often
• where you repeat actions
• what seems inefficient
• what you abandon halfway

That interpretation can feel strikingly human. It’s not “you used tool X 52 times,” it’s “you tend to start workflows but don’t close the loop.” That’s new territory for a dev tool.

1) “Human‑like evaluation” is both powerful and unsettling

The author’s reaction is consistent with what I’ve seen in production analytics: a narrative summary makes people feel judged, even when the data is neutral. Here, /insights feels like getting performance feedback.

Retrieve: AI feedback shifts from descriptive to interpretive. That’s high‑leverage—but it also increases friction.

2) Misclassification happens when context is missing

Claude classified the author as a “browser automation expert” because of long, heavy Chrome sessions. That was true in behavior but not necessarily in intent. This is the classic telemetry vs. intent gap.

If we treat /insights as ground truth, we will over‑optimize for the wrong label.

3) “Soft” negative feedback on conversation drop‑offs

The report noted unfinished conversations. The author admits this is sometimes due to mis‑configured tools, sometimes because quick experiments were done and abandoned—especially after adopting fast, Codex‑like workflows.

This is a critical insight: the system doesn’t know why you stopped. It only sees that you did.

4) /insights is not just reporting—it’s nudging

The report includes actionable suggestions (skills, agents, hooks), suggesting how to structure repeated work. That’s closer to workflow coaching than usage analytics.

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💡 Innovation: Turning AI evaluation into a production advantage

Here’s how I’d integrate /insights into a real studio workflow without letting it become noise.

1) Treat /insights like a playtest—valuable, not authoritative

If player telemetry says “Level 3 is too hard,” we don’t immediately nerf the boss. We triangulate: feedback + retention + completion rate. /insights is the same.

Rule: Use it as a signal, never as a verdict.

2) Add “intent tags” to reduce misclassification

The post highlights how behavior gets mislabeled. We can fix this by adding lightweight intent metadata in our process:

• prefix experimental sessions with “EXP:”
• tag automation runs with “BENCH:”
• keep a scratchpad explaining why you started a long run

This way, when /insights summarizes, the context is already inside the data.

3) Build a feedback loop: report → reflection → action

Here’s a minimal loop that makes /insights useful instead of anxiety‑inducing:

graph LR
  A[/insights Report] --> B[Self‑Reflection]
  B --> C[Actionable Change]
  C --> D[Workflow Update]
  D --> A

4) Use /insights to drive tooling, not ego

The post notes that /insights recommends Skills / Agents / Hooks. That’s a hint: it wants you to encode your patterns.

If you see “frequent repetitive browser automation,” then:

• create a reusable agent task
• wrap it in a CLI shortcut
• keep the report focused on higher‑level decision‑making

5) Make the “stop condition” explicit

A recurring issue is unfinished chats. I’d formalize stop states in my toolchain:

• STOP: experiment done, results captured
• STOP: blocked on external input
• STOP: deprioritized

This turns ambiguous dropout into explicit state.

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🧪 Practical Example: A tiny helper for intent tagging

# Simple helper to tag sessions for cleaner /insights reports
from datetime import datetime

def tag_session(intent: str, summary: str) -> str:
    ts = datetime.now().strftime("%Y-%m-%d %H:%M")
    return f"[{ts}] INTENT={intent} :: {summary}"

print(tag_session("EXP", "Prototype agent‑based QA workflow"))
# Output: [2026-02-06 22:40] INTENT=EXP :: Prototype agent‑based QA workflow

This can live in your scratchpad, commit notes, or even your agent prompts. The goal: give the evaluator context it can’t infer.

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Key Takeaways

Insight	Implication	Next Steps
/insights feels like human feedback	It will trigger emotion, not just analytics	Use reflection, not reaction
Context gaps cause mislabels	Behavioral signals ≠ intent	Add lightweight intent tags
Drop‑offs are ambiguous	Tool can’t infer “why”	Explicit stop states
Recommendations are tooling hints	Encode patterns into Skills/Agents	Operationalize feedback

New Questions

• How do we design AI feedback that is candid but not demotivating?
• Can we build “intention-aware telemetry” so insights are less biased?
• What’s the right cadence for AI feedback so it feels helpful, not invasive?

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References

• Source post: https://digitalbourgeois.tistory.com/m/2716
• Claude Code docs: https://code.claude.com/docs/en
• X thread (feature announcement): https://x.com/i/status/2019173731042750509