LLM Roadmap

Interview Prep

System design questions, behavioral prompts, and the mental models behind them. Work through these after completing Levels 3–5.

System Design

Each prompt includes hints — try to answer without them first, then use the hints to pressure-test gaps.

Behavioral

STAR format for each. Have at least one concrete story ready per question.

1

Tell me about a system you built that failed in production. How did you diagnose and fix it?

STAR format. Emphasise what you learned and the observability tooling you added afterward.

2

Describe a time you had to make a meaningful trade-off between model quality and latency or cost.

Concrete numbers help (e.g., "dropping from GPT-4 to Haiku cut cost 10x with 5% quality drop on our eval set").

3

How do you decide when an LLM feature is "good enough" to ship? Walk me through your evaluation process.

Shows eval maturity. Mention golden datasets, LLM-as-judge, user study, and rollout strategy.

4

How would you explain hallucinations — and the limits of your mitigation strategies — to a non-technical stakeholder?

Tests communication. Frame around user impact and the system guardrails, not just model internals.

5

How do you stay current with the LLM landscape given the pace of change? What did you read or build last week?

Have a genuine, specific answer. Arxiv Sanity, Hugging Face blog, Chip Huyen newsletter, and actual side projects are all valid.

6

Describe a project where you owned both the ML component and the backend/infra. What did you learn?

LLM engineering roles blur the ML/backend boundary. Show you are comfortable in both.

7

Tell me about a time you pushed back on using an LLM when a simpler solution was better.

Shows engineering judgement. LLMs are not always the right tool.

8

How do you work with product/design on AI features where user expectations are hard to set?

Focus on setting clear eval criteria upfront, iterating with prototypes, and managing "AI magic" expectations.

Further reading