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GusevV1987GusevV1987/ai-workspace-kit/skills/plan-ceo-review/SKILL.md

plan-ceo-review

Skill2 starsChanged 8 months agoMITView on GitHub

Founder-mode strategic plan review. Stress-tests plans across 11 dimensions from a CEO perspective — business risk, scope creep, failure modes, and go/no-go readiness.

49 other projects use a version of this.

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The file

We split this skill into the rules it gives an agent

7 rules. 0 are common, 7 are distinctive, and 0 are very specific to this project.

  • 0

    Common

    Most of the 41 edited versions we read keep these.

  • 7

    Distinctive

    This author's own choices. Worth a look.

  • 0

    Very specific

    Tied to their project's names, files or tools. Probably skip.

  • Common
  • Distinctive
  • Very specific
  1. Distinctive:

    Before executing any significant plan, review it through the lens of a founder who owns the outcome.

    line 13
  2. Distinctive:

    Before executing a multi-step implementation plan

    line 17
  3. Distinctive:

    Before any major architecture decision

    line 18
  4. Distinctive:

    When a plan touches production systems, user data, or costs money

    line 19
  5. Distinctive:

    When you want a "would I bet the company on this?" gut check

    line 20
  6. Distinctive:

    If this turns out to be wrong, how hard is it to undo?

    line 51
  7. Distinctive:

    When recommending scope changes, choose one:

    line 97

“Common” is measured: kept by at least 6 in 10 of the 41 edited versions of this file we could read. “Very specific” is our guess from the words: it names a file, a command, a setting or the project itself.

Keep what fits and drop the rest. Your version, ready for your agents.
Files
SKILL.md

Plan — CEO Review

The Rule

Before executing any significant plan, review it through the lens of a founder who owns the outcome.

When to Use

  • Before executing a multi-step implementation plan
  • Before any major architecture decision
  • When a plan touches production systems, user data, or costs money
  • When you want a "would I bet the company on this?" gut check

The 11 Review Dimensions

Score each 1-10. Flag anything below 7.

1. Problem Clarity

Is the problem statement specific and falsifiable? Can you explain what success looks like in one sentence?

2. Scope Discipline

Does the plan do exactly what's needed — no more, no less? Is every item justified? Would you cut anything if you had half the time?

3. Architecture Fit

Does this fit into the existing system, or does it introduce a new pattern? New patterns need 3x the justification.

4. Failure Modes

What happens when this breaks? What's the blast radius? Is there a rollback path? How long until someone notices?

5. Security Surface

Does this expand the attack surface? Does it handle credentials, user data, or external inputs? What's the worst case if an attacker targets this specifically?

6. Dependency Risk

What external systems does this rely on? What happens if they're down, slow, or change their API? Are there fallbacks?

7. Operational Burden

Who maintains this after it ships? Does it add monitoring, alerts, or manual intervention? Does it make the on-call rotation harder?

8. Cost Impact

What does this cost to run? Does it scale linearly or exponentially? Are there usage-based charges that could surprise you?

9. Reversibility

If this turns out to be wrong, how hard is it to undo? Prefer reversible decisions. Irreversible ones need more scrutiny.

10. Timeline Realism

Is the time estimate honest? Does it account for testing, deployment, documentation, and the inevitable surprises? Double your gut estimate.

11. Strategic Alignment

Does this move the company closer to its core goal, or is it a detour? Would you still do this if you only had 3 months of runway?

Output Format

## CEO Review: [Plan Name]

| Dimension | Score | Notes |
|-----------|-------|-------|
| Problem Clarity | X/10 | |
| Scope Discipline | X/10 | |
| Architecture Fit | X/10 | |
| Failure Modes | X/10 | |
| Security Surface | X/10 | |
| Dependency Risk | X/10 | |
| Operational Burden | X/10 | |
| Cost Impact | X/10 | |
| Reversibility | X/10 | |
| Timeline Realism | X/10 | |
| Strategic Alignment | X/10 | |

**Average:** X/10

### Failure Modes Registry
1. [Specific failure mode] → [Mitigation or acceptance]
2. [Specific failure mode] → [Mitigation or acceptance]

### Scope Recommendations
- **Keep:** [Items that are essential]
- **Cut:** [Items that can wait]
- **Add:** [Missing items that should be there]

### Verdict
[GO / GO WITH CHANGES / NO-GO]

[One paragraph explaining the verdict]

Scope Postures

When recommending scope changes, choose one:

PostureWhen to use
ExpandCritical gaps found — plan is incomplete without these additions
HoldPlan is solid as-is
TrimPlan has nice-to-haves that increase risk without proportional value
ReducePlan is too ambitious — cut to the essential core

Key Principle

This review represents the founder's perspective: what matters is whether this plan moves the business forward with acceptable risk. Technical elegance doesn't matter if the business case is weak. Speed matters, but not at the cost of reliability.

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