After 5+ years of freelancing and talking to hundreds of potential clients, I know exactly which questions separate founders who hire well from those who end up disappointed. Here are the 10 questions you should ask any freelance developer before signing a contract — along with what good and bad answers look like. ## Question 1: "Can you show me a project similar to mine?" **Why it matters:** Relevant experience is the single strongest predictor of project success. A developer who has built 5 SaaS platforms will build yours in half the time and with better architecture than someone doing it for the first time. **Good answer:** "Yes, here is [specific project]. It had similar requirements — [details]. Here is what I learned from it that applies to your case." **Red flag:** "I have not built exactly that, but I can learn quickly." Learning on your budget is expensive. **Scoring:** Full portfolio match = 10 points. Partial match = 5 points. No relevant experience = 0 points. ## Question 2: "How would you architect this project?" **Why it matters:** This reveals technical depth without requiring you to be technical. A good developer will think out loud about trade-offs. **Good answer:** "For your use case, I would use [framework] because [reason]. The database would be structured as [brief explanation]. For the API, I would use [approach] because [trade-off consideration]." **Red flag:** "I will figure that out once we start." Architecture decisions made on the fly lead to rewrites later. ## Question 3: "What is your estimated timeline, and how did you arrive at it?" **Why it matters:** The breakdown matters more than the number. A developer who can decompose the project into milestones understands its scope. **Good answer:** "Based on the requirements, I estimate 4–6 weeks. Here is the breakdown: authentication system — 3 days, core features — 2 weeks, integrations — 1 week, testing and deployment — 3 days. The range accounts for unknowns in the API integration." **Red flag:** "About a month." No breakdown means they have not thought it through. ## Question 4: "How do you handle scope changes?" **Why it matters:** Every project has scope changes. The process for handling them determines whether changes cause delays and budget overruns or are managed smoothly. **Good answer:** "I document the original scope clearly. When changes come up, I assess the impact on timeline and cost, send you an updated estimate, and we agree before I implement. Small changes within reason I absorb. Significant changes get a mini-proposal." **Red flag:** "We will deal with it as it comes." This leads to disputes about what was included. ## Question 5: "What is included in your price?" **Why it matters:** Hidden costs are the number one source of budget surprises. Get everything in writing. **Good answer:** "My price includes: development, basic UI (or integration with your design), deployment to your server, documentation, and 30 days of bug fixes. Not included: graphic design, content writing, third-party API costs, and hosting fees. Here is what those typically cost." **Red flag:** "Development." Too vague. Does it include deployment? Testing? Bug fixes? ## Question 6: "How will you keep me updated on progress?" **Why it matters:** Communication failures kill more projects than technical failures. Establish the cadence upfront. **Good answer:** "I send a weekly update every [day] with what was completed, what is next, and any blockers. For urgent items, I message via Telegram/Slack immediately. You will have access to a staging environment to see progress in real time." **Red flag:** "I will send you the final product when it is done." Four weeks of silence followed by a delivery that misses the mark. ## Question 7: "What happens if you cannot finish the project?" **Why it matters:** Life happens. Illness, emergencies, burnout. Knowing the exit plan protects both sides. **Good answer:** "My contract includes a termination clause. If I cannot continue, you receive all code and documentation completed to date. I use Git, so you have full version history. I can help find a replacement developer and brief them." **Red flag:** "That will not happen." Overconfidence about never having problems is itself a problem. ## Question 8: "Can I see your code quality?" **Why it matters:** Clean code is easier to maintain, extend, and hand off. Messy code creates technical debt that costs more to fix than the original development. **Good answer:** "Here is my GitHub profile. This [repository] shows my code style. I follow [PEP 8 / specific style guide], write docstrings for complex logic, and include basic tests." **Red flag:** "My code is proprietary / under NDA." While some work is genuinely confidential, a developer with zero public code is harder to evaluate. ## Question 9: "What is your payment structure?" **Why it matters:** Payment structure aligns incentives. Milestone-based payments protect both sides. **Good answer:** "30% upfront to start work, 30% at the midpoint milestone (working demo), 40% on final delivery and your acceptance. I do not ask for more than 30% upfront because you need to see progress before committing more." **Red flag:** "100% upfront" or "50% upfront with the rest on completion" with no intermediate milestones. The first is a major risk. The second gives you no leverage during the crucial middle phase. ## Question 10: "What do you NOT do well?" **Why it matters:** Self-awareness is the mark of a professional. Every developer has weaknesses, and the good ones are honest about them. **Good answer:** "I am a backend specialist. I can build a functional UI, but if you need pixel-perfect design, you should work with a designer. I also do not do native mobile apps — I focus on web and API development." **Red flag:** "I can do anything." Nobody is equally good at everything. A developer who claims otherwise is either exaggerating or has not done enough work to discover their limitations. ## Scoring Framework Use this scoring to compare developers: | Category | Weight | Score (0–10) | |----------|--------|-------------| | Relevant portfolio | 30% | | | Communication quality | 25% | | | Technical depth | 20% | | | Process maturity | 15% | | | Pricing transparency | 10% | | | **Total** | **100%** | | A developer scoring 7+ across all categories is a strong hire. Below 5 in any category — especially communication or relevant experience — is a warning sign. ## The Meta-Question Beyond these 10 questions, pay attention to one thing: **does the developer ask YOU questions?** A developer who listens to your requirements and immediately quotes a price has not understood the project. A developer who asks clarifying questions about your users, your business model, and your success criteria is the one who will build the right thing. ## My Approach When potential clients contact me, I spend the first 30 minutes asking about their business — not their technical requirements. I want to understand who their users are, what problem they are solving, and what success looks like. Only then do I discuss architecture, timeline, and pricing. This approach has led to 15+ successful projects and long-term client relationships. If you are evaluating developers for your project, I am happy to have a free consultation — even if you end up choosing someone else. Understanding your project well enough to give honest advice is part of my process.