timdevai /cs:cto-review — CTO Forcing Questions
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-architectfor 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
- Run the tech debt analyzer + team scaling calculator
- Define the scaling-cliff hypothesis explicitly
- Cross-check with cs-ciso-advisor for security implications
- 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
Related
- Agent:
cs-cto-advisor - Skill:
cto-advisor - SLO:
../../../../engineering/slo-architect/
Version: 1.0.0