CTO's Guide to Technical Interview Process for Contract Engineers

Interviewing for a contract role should be faster than interviewing for a permanent one — not slower. You don't need culture fit, career trajectory assessment, or 5 rounds of interviews. You need to know: can this person do the specific technical work, and can they communicate well enough to work remotely and asynchronously? That's 2 hours if you design the process right.

The 2-Hour Framework

Round 1: Async Technical Screen (60 min, candidate's own time)

Send a single, well-defined technical problem relevant to the actual work. Examples:

• "Here's a FastAPI endpoint with a performance problem. Identify the issue, propose a fix, and explain the trade-offs."
• "Review this PR and provide written feedback as you would for a team member."
• "Design the data model for this feature. Document your assumptions and alternatives considered."

Async format (written response or Loom video) serves two purposes: it tests the technical skill AND it tests written communication — which is how they'll collaborate with you every day.

Round 2: Live Technical Conversation (45 min)

Not a quiz. A conversation about their experience, their approach to problems, and a brief deep-dive into their async submission. Questions to ask:

• "Walk me through the most technically complex thing you've built. What were the trade-offs you made?"
• "Tell me about a time you disagreed with a technical decision on a project. What did you do?"
• "What's one thing you'd do differently if you were starting that project again?"

Round 3: Domain Fit Check (15 min)

Quick call with whoever will work most closely with this person. Not a technical round — a "can we work together?" check. If they need to attend standups with your product team, a 15-min call tells you everything.

What Not to Do

• Don't run 5+ interview rounds — contractors have multiple offers and will drop out
• Don't use irrelevant algorithm puzzles — they test interview preparation, not engineering ability
• Don't delay feedback — contract candidates move fast; a 1-week feedback loop loses good people

• → CTO's Guide to Evaluating Contractors
• → How to Vet Remote Developers
• → How to Write a JD for Contract Developers