An AI-powered CLI tool that simulates real contract negotiations — with a live AI counterparty, turn-by-turn scoring, and senior counsel-level feedback.
Contract Negotiation Simulator puts you across the table from an AI counterparty counsel. You defend your position on a real clause (liability cap, sub-processor approval, IP ownership, termination for convenience), the AI pushes back with professional legal language, and at the end of the session you receive a structured scorecard with coaching feedback.
Built for:
- In-house counsel preparing for difficult negotiations
- Legal teams training junior lawyers on commercial contracts
- Legal tech enthusiasts exploring agentic AI in legal workflows
| Feature | Description |
|---|---|
| Live AI counterparty | Claude plays an experienced opposing counsel with a real mandate |
| Structured scorecard | 4 dimensions: Playbook Adherence, Legal Precision, Strategy, Commercial Awareness |
| Senior counsel feedback | Best move, missed opportunity, suggested closing position |
| Session export | Every negotiation saved as .json for review |
| Difficulty levels | Easy / Medium / Hard scenarios |
| Multi-round | Configurable turn count per scenario |
| # | Clause | Contract Type | Difficulty |
|---|---|---|---|
| 1 | Limitation of Liability (12-month ACV cap) | SaaS MSA | Medium |
| 2 | Sub-processor Approval (GDPR Art. 28) | DPA | Hard |
| 3 | IP Ownership & Work for Hire | CSA | Medium |
| 4 | Termination for Convenience | MSA | Easy |
git clone https://github.com/marcoderoni/contract-negotiation-simulator.git cd contract-negotiation-simulator
pip install -r requirements.txt
export ANTHROPIC_API_KEY="your-key-here"
python simulator.py
- Choose a scenario — pick a clause type and difficulty
- Read the opening clause — this is your starting position
- Respond to the counterparty — propose redlines, make arguments, concede strategically
- Finish all turns (or type
scoreto end early) - Receive your scorecard — with dimensional scores and coaching feedback
FINAL SCORE: 74/100 · Grade: B
Playbook Adherence ███████░░░ 70 Defended the cap but accepted a carve-out outside mandate.
Legal Precision ████████░░ 80 Clause language was clean and correctly scoped.
Negotiation Strategy ███████░░░ 72 Good use of fallback; missed a sequencing opportunity.
Commercial Awareness ████████░░ 75 Correctly tied liability cap to contract value.
Best move: Linking the liability cap to the premium paid for the service.
Missed opportunity: Proposing a mutual cap to reframe the asymmetry.
Senior counsel close: "We can accept a 24-month cap for data breach events only, mutual..."
This simulator is part of a broader open-source collection of AI-powered legal tools:
- Legal AI Toolkit (https://github.com/marcoderoni/Legal-AI-Toolkit) — contract review, comparison, clause drafting
- Contract Negotiation Simulator (this tool) — AI counterparty + scoring
Training and educational purposes only. Not legal advice. All scenarios are fictional.
Marco Deroni — Senior Legal Counsel (Commercial) | CIPP-E | LL.M.
LinkedIn: https://www.linkedin.com/in/marcoderoni GitHub: https://github.com/marcoderoni
MIT — see LICENSE