Engineering case study
GermanGuess
GermanGuess is a personal language-learning system using hybrid validation: rules check grammar, LLMs vary exercises. Live at germanguess.com — the first step of my AI journey from enterprise programme leadership to practical AI building.
Background
As a programme lead in Germany I need B1 German for daily work. Existing apps do not cover my learning path. I built GermanGuess to understand where LLMs help with structured validation — and where they do not.
Problem
Professionals learning German need consistent, trustworthy practice — the same quality bar applies when scaling exercises without heavy manual review.
Goals
- Grammar exercises with immediate, reliable feedback
- Hybrid validation: rules + LLM variation
- Measurable learning curve across sessions
- Understand where LLMs fail in learning products
Architecture
Current implementation — based on what is built today.
Technology stack
React · TypeScript · Python · LLM APIs · PostgreSQL
Engineering challenges
- Reliably generating grammatically correct exercises
- Catching hallucinations and incorrect corrections
- Modeling learning progress meaningfully in PostgreSQL
- Keeping feedback loops faster than traditional learning apps
Trade-offs
- LLM variation vs. reliable rule checking — hybrid validation required
- Feature scope deliberately limited in favour of exercise quality
- Single-user focus — no multi-tenant architecture
Lessons learned
- AI works well for variation, less for reliable rule checking without additional logic
- Feedback loops must be faster than in traditional learning apps
- Personal projects make LLM limitations most visible
Current status
Live for users. Gathering feedback. Building additional learning modes.
Future improvements
- Extended grammar modules (subjunctive, passive voice)
- Better hallucination detection in LLM feedback
- Visualise learning progress and target weak areas for repetition
Estimated milestones
- Q2 2026 — Subjunctive module with rule validation
- Q3 2026 — Hallucination guardrails for correction feedback
- Q4 2026 — Weak-area dashboard