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/cs:cto-review — CTO Forcing Questions

C-Level Advisory cto-review Source

Install: claude /plugin install c-level-skills

Command: /cs:cto-review <plan>

Pressure-tests architecture and engineering scaling decisions. Six questions to surface the next scaling cliff before you hit it.

When to Run

  • Before approving a major architecture change
  • Before doubling the engineering team
  • Before a build-vs-buy decision > $100K/year
  • When a system is showing reliability stress (SLOs missed)
  • Before committing to a new platform / language / DB

The Six CTO Questions

1. Scaling Cliff

Where does the current architecture break, in terms of users / requests / data volume? - Be specific. "It breaks at 10× current load because the primary DB writes saturate." - If you don't know, run a load test before deciding.

2. Tech Debt Inventory

What's the top tech debt item, what's it costing per week, and when does it become blocking? 

python ../../../skills/cto-advisor/scripts/tech_debt_analyzer.py

3. Team Scaling

For each open req, what's the ramp time and contribution model? 

python ../../../skills/cto-advisor/scripts/team_scaling_calculator.py

4. Build vs Buy

Why are we building this instead of buying it — and what's the 3-year TCO of each? - If "we want control" or "it's not that hard" — push back. - If the answer is "this is our core moat," build.

5. SLO / Reliability

What are the SLOs for this system and what's the current error budget burn? - Without an SLO, you can't reason about reliability tradeoffs. - See engineering/slo-architect for SLO design.

6. Security & Compliance Surface

What does this expose, and has cs-ciso-advisor signed off? - Architecture decisions are compliance decisions. - Loop in cs-ciso-advisor before commit.

Workflow

  1. Run the tech debt analyzer + team scaling calculator
  2. Define the scaling-cliff hypothesis explicitly
  3. Cross-check with cs-ciso-advisor for security implications
  4. Apply the verdict

Output Format

# CTO Review: <plan>
**Date:** YYYY-MM-DD

## Scaling Cliff
- Current capacity: <metric>
- Break point: <metric>
- Headroom: X months at current growth

## Tech Debt
- Top item: <description>
- Cost per week: $X or N eng-hours
- Blocking date estimate: <date>

## Team
- Open reqs: N
- Median ramp: X months
- Contribution model: <pairing / squad / area>

## Build vs Buy
- 3-year build TCO: $X
- 3-year buy TCO: $X
- Strategic fit: <core / context>
- Decision: BUILD | BUY

## Reliability
- SLO defined: yes / no
- Error budget burn: X% (target < Y%)

## Security
- cs-ciso sign-off: ✅ / ❌

## Verdict
🟢 SHIP | 🟡 SHARPEN | 🔴 BLOCK

## Next Steps
[3 concrete actions]

Routing

  • /cs:ciso-review — mandatory if data surface changes
  • /cs:cfo-review — for build-vs-buy > $100K
  • /cs:execute — quarterly plan
  • /cs:boardroom — for architecture pivots

Version: 1.0.0