Author: Savas Tutumlu, Co-Founder & CTO
Experience: MIT-trained • 100+ projects quoted • Sat on both client and vendor side of evaluations
Published: November 17, 2025 • Reading time: 9 minutes
Most buyers ask the wrong first question: “What’s your hourly rate?” Rate matters—but the difference between a successful build and a slow-motion disaster almost always comes down to how the team works, not their sticker price.
The questions below are grouped so you can run a structured conversation with any software development company, whether they’re in Texas, offshore, or across North America. Use them alongside our 2025 pricing guide and RFP template.
Quick Answer: The 5 Themes You Must Cover
- Fit: Have they built anything like what you want before?
- Architecture & quality: How do they design, test, and maintain systems?
- Team: Who actually works on your project—and how senior are they?
- Process & pricing: How do they estimate, communicate, and handle change?
- Ownership & risk: Who owns code, infra, and what happens when things go wrong?
1. Fit & Relevant Experience
- “Tell me about 2–3 projects most similar to what we’re planning.”
Follow‑up: industry, budget range, timeline, and live URL if possible. - “What changed between the original scope and what actually shipped?”
You’re looking for honesty about scope evolution, not a fairy tale. - “What type of work do you say no to?”
Real teams know their lane; generalists who say “everything” rarely excel at anything.
2. Architecture & Technical Depth
- “If you were designing our system, how would you break it down at a high level?”
Look for sane boundaries (modules/services), clarity about trade‑offs, and mention of observability. - “Which parts of the system are likely to be most complex or risky?”
Any answer that pretends there is no risk is itself a risk. - “Show me an architecture diagram and a README from a similar project.”
You want to see how they communicate design to non‑authors.
3. Team Composition & Continuity
- “Who will be the lead engineer or architect on our project?”
Ask to meet them, not just a salesperson. - “How many projects are they actively leading right now?”
Three is normal, ten is a red flag. - “What happens if a senior engineer leaves mid‑project?”
Listen for documentation, code review discipline, and pairing—not just “we’ll replace them.”
4. Delivery Process & Communication
- “Walk me through a typical 2‑week sprint with your team.”
How do they plan, build, demo, and incorporate feedback? - “How often will we see working software?”
Good answer: every sprint. Bad answer: “Every few months when we’re ready.” - “What tools do you use for backlog, documentation, and deployment?”
Look for a coherent stack, not improvisation every time. - “How do you handle scope changes?”
Clarify change‑control, pricing impact, and how decisions are documented.
5. Pricing, Estimates & Models
Use this section in combination with our pricing breakdown and upcoming article on fixed‑bid vs T&M vs dedicated teams.
- “How do you estimate projects—and how accurate are your estimates historically?”
Ask for examples where they were off and what they learned. - “Which pricing model do you recommend for our project and why?”
You’re testing for alignment with your risk tolerance, not just their cash‑flow preferences. - “What’s included in your price—and what isn’t?”
Clarify environments, monitoring, QA, project management, and post‑launch support.
6. Ownership, Handover & Support
- “Who owns the source code, infrastructure accounts, and CI/CD pipelines?”
The answer should be: you do. - “How is knowledge captured so we’re not dependent on one or two people?”
Listen for written documentation, architecture overviews, and runbooks. - “What support and maintenance options do you offer after launch?”
Map their retainers or SLAs to your internal capacity.
7. References & Proof
- “Can we speak with 2–3 clients whose projects look like ours?”
Ideally, at least one technical stakeholder. - “Which case studies best reflect what we’re trying to do?”
Review them ahead of time—see, for example, our ERP efficiency case study. - “What’s a project that went badly—and what did you change afterwards?”
Mature teams have scars and lessons, not just success stories.
8. Turn These Questions into a Simple Scorecard
For each vendor, score answers on a simple 1–5 scale for:
- Technical depth and clarity.
- Process maturity and communication.
- Cultural fit and transparency.
- Alignment with your budget and risk profile.
If you’re currently shortlisting partners, you can also:
- Use our RFP template as the structure for written responses.
- Anchor budget expectations with the company pricing guide.
- Compare models using our upcoming fixed‑bid vs T&M vs dedicated team breakdown.
And if you want a second opinion on a proposal you’ve already received, you can always book a short call via our pricing page. We’re happy to tell you, candidly, whether we think the plan will work—or not.