# Session Doubt

> End-of-session doubt enumeration before claiming substantive work done. Surfaces (1) what the agent is least confident about — then root-causes each item — and (2) the biggest thing the user may not realize about the situation. A two-question reflective close-out, distinct from test-running verification. Triggers "/session-doubt", "doubt check", "what are you least confident about", "what am I mi…

- **Type:** Skill
- **Install:** `agentstack add skill-ao92265-claude-code-playbook-session-doubt`
- **Verified:** Yes — security-reviewed for prompt injection and unsafe behavior
- **Seller:** [ao92265](https://agentstack.voostack.com/s/ao92265)
- **Installs:** 0
- **Category:** [Agent Skills](https://agentstack.voostack.com/c/agent-skills)
- **Latest version:** 0.1.0
- **License:** MIT
- **Upstream author:** [ao92265](https://github.com/ao92265)
- **Source:** https://github.com/ao92265/claude-code-playbook/tree/main/skills/session-doubt

## Install

```sh
agentstack add skill-ao92265-claude-code-playbook-session-doubt
```

Requires the [AgentStack CLI](https://agentstack.voostack.com/docs/cli). Works with Claude Code, Cursor, and any MCP-compatible agent.

## About

# session-doubt

Reflective close-out for substantive work. Two questions, asked in order. Source: end-of-session technique (Sam Altman's Q1 + a Claude-suggested Q2) — "1 in 4 times it surfaces a huge deal."

Run AFTER the work is otherwise complete (and ideally after `/done` / verification-before-completion has run). This is reflection, not test execution — the two are complementary, not substitutes.

## Q1 — Least confident

Ask yourself, honestly and without flattering the work:

> What am I least confident about right now? Enumerate everything.

- List **every** item, not a curated top-3. Aim for 5–8. Include things that feel minor.
- For each: one line stating the doubt + why.
- Then **root-cause the real ones**: pick the items where being wrong would actually matter and investigate each exhaustively (read the code, run the check, trace the path) until you understand the root cause — do not stop at restating the doubt.
- Be specific. "Error handling might be incomplete" is useless. "If the upload retries after a 413, we double-charge because the idempotency key is regenerated per-attempt — unverified" is useful.

## Q2 — Biggest blind spot

Then ask:

> What is the biggest thing the user does not realize about this situation right now?

- One thing. The single highest-leverage reframe, risk, or connection the user is most likely missing.
- It should change a decision, not just inform. Prefer the insight that contradicts or reframes something the user (or you) already assumed.

## Output

```
**Q1 — least confident (root-caused):**
1.  —  → 
2. ...

**Q2 — biggest blind spot:**

```

Keep it tight. No reassurance padding. If genuinely nothing is uncertain, say so plainly — do not manufacture doubt to fill the list.

## Source & license

This open-source skill is cataloged on AgentStack and links to its original source — we do not rehost the code.

- **Author:** [ao92265](https://github.com/ao92265)
- **Source:** [ao92265/claude-code-playbook](https://github.com/ao92265/claude-code-playbook)
- **License:** MIT

Install and usage instructions live in the source repository linked above.

## Pricing

- **Free** — Free

## Security capabilities

Automated source analysis of v0.1.0 — what this tool can access:

- **Network access:** no
- **Filesystem access:** no
- **Shell / process execution:** no
- **Environment & secrets:** no
- **Dynamic code execution:** no

*"Yes" means the capability is present in the source — more access means more to trust, not that it is unsafe.*


## Versions

- **0.1.0** — security scan: passed — Imported from the upstream source.

## Links

- Listing page: https://agentstack.voostack.com/l/skill-ao92265-claude-code-playbook-session-doubt
- Seller: https://agentstack.voostack.com/s/ao92265
- Browse the marketplace: https://agentstack.voostack.com/browse

---
Listed on AgentStack — the marketplace for AI agent skills and MCP servers. Every listing is security-reviewed. Creators keep 70%.