How to evaluate a software development partner: 15 questions to ask

You need custom software built. Maybe it's a customer portal. Maybe it's internal tooling. Maybe it's the system that will run your entire operation.

The stakes are high. Get it wrong, and you're looking at months of delays, budget overruns, a product that doesn't work, and the painful process of starting over with someone else.

The problem: Every development company sounds good in their sales pitch. They all claim to be experts. They all promise on-time delivery. They all say they're different.

So how do you tell who's actually good?

Here are 15 questions that will separate genuine partners from vendors who'll take your money and disappear.

Questions about their process

1. What happens when requirements change mid-project?

Why it matters: Requirements always change. Anyone who pretends otherwise is either lying or inexperienced. The question is how they handle it.

Red flags:

• "We lock down requirements upfront and don't allow changes"
• "Changes are billed at premium hourly rates"
• Vague answers about "being flexible"

Good answers:

• Clear change management process
• Regular checkpoints where scope can be adjusted
• Transparent communication about trade-offs (time, budget, scope)
• Experience with iterative development methodologies

2. Who will actually work on my project?

Why it matters: Many firms sell you on their senior talent, then staff your project with juniors. You deserve to know who's actually doing the work.

Red flags:

• "We'll assign the best available resources"
• Can't name specific people
• Heavy use of contractors or offshore teams without disclosure

Good answers:

• Specific names and backgrounds of team members
• Introduction to the actual team before signing
• Clear explanation of who does what
• Transparency about any offshore or contractor involvement

3. How do you ensure you understand our business, not just our requirements?

Why it matters: The best technical solution depends on understanding the business problem. Partners who skip this step build technically correct systems that don't actually solve your problem.

Red flags:

• Jump straight to technical solutioning
• "Just give us the requirements and we'll build it"
• No discovery phase in their process

Good answers:

• Dedicated discovery phase to understand your business
• Questions about your customers, operations, and strategy
• Interest in the "why" behind requirements
• Experience in your industry or similar businesses

4. What's your approach to testing and quality?

Why it matters: Testing is often the first thing cut when projects run behind. But skipping it means bugs in production, which means unhappy users and expensive fixes.

Red flags:

• "We test as we go" (often means minimal testing)
• No dedicated QA process
• Testing is an afterthought or add-on

Good answers:

• Automated testing as part of the development process
• Dedicated QA before each release
• Different types of testing (unit, integration, user acceptance)
• Clear process for handling bugs found in production

5. How do you handle security and compliance?

Why it matters: Security vulnerabilities can be catastrophic. If you're in a regulated industry, compliance isn't optional.

Red flags:

• "We follow best practices" (vague)
• No specific security procedures
• Security is an add-on service, not built-in

Good answers:

• Specific security practices (code review, penetration testing, dependency scanning)
• Experience with relevant compliance frameworks (HIPAA, SOC 2, PCI, etc.)
• Security considerations built into architecture, not bolted on
• Clear data handling and privacy practices

Questions about outcomes

6. What does "done" look like?

Why it matters: If you don't agree on what success means upfront, you'll argue about it later. Many projects drag on because "done" was never defined.

Red flags:

• "When you're happy with it"
• Vague acceptance criteria
• No clear definition of project completion

Good answers:

• Specific, measurable acceptance criteria
• Clear handoff process
• Definition of minimum viable product vs. full scope
• Documented expectations for launch-readiness

7. How do you communicate progress and problems?

Why it matters: Projects go wrong all the time. The question is whether you find out about problems when they're small and fixable — or when they're disasters.

Red flags:

• "We'll send you weekly status emails"
• No access to project tracking tools
• Problems are hidden until they're unavoidable

Good answers:

• Regular, structured check-ins (weekly or more frequent)
• Access to real-time project dashboards
• Proactive communication about risks and issues
• Clear escalation paths when things go wrong

8. What happens after launch?

Why it matters: Launch isn't the end — it's the beginning. You need to know who supports the system, how bugs get fixed, and what happens when you need enhancements.

Red flags:

• "We hand it off and move on"
• Support is a separate, expensive contract
• No ownership of post-launch issues

Good answers:

• Clear warranty period for launch bugs
• Ongoing support options with defined SLAs
• Transition plan for knowledge transfer
• Long-term partnership mindset, not project-based thinking

Questions about credibility

9. Can you share references from similar projects?

Why it matters: Past performance predicts future performance. References let you verify their claims.

Red flags:

• "Our clients prefer confidentiality" (sometimes true, often an excuse)
• No references available
• References only from very different types of projects

Good answers:

• Multiple references from similar scope/industry
• Willingness to connect you directly with past clients
• Case studies with specific metrics and outcomes
• Long-term client relationships (not just one-off projects)

10. What's your experience with our industry/technology?

Why it matters: Industry experience means faster ramp-up, fewer mistakes, and better understanding of your constraints. Technology expertise means better architecture and fewer technical dead-ends.

Red flags:

• "We're fast learners" (learning on your dime)
• No relevant experience
• Overstating tangential experience

Good answers:

• Specific examples in your industry or similar
• Deep expertise in relevant technologies
• Understanding of industry-specific regulations and constraints
• Honest acknowledgment of gaps with plan to address them

11. How do you handle scope creep?

Why it matters: Scope creep is the #1 killer of software projects. It happens on every project. The question is how it's managed.

Red flags:

• "We're flexible with scope" (often means no boundaries)
• Blame the client for scope creep
• No process for evaluating change requests

Good answers:

• Clear process for documenting and evaluating change requests
• Transparent discussion of trade-offs
• Regular scope reviews to catch creep early
• Experience maintaining scope discipline while staying flexible

12. What's your team's turnover rate?

Why it matters: High turnover means your project gets handed off mid-stream. Knowledge is lost. Momentum dies. Quality suffers.

Red flags:

• Won't answer the question
• High turnover (above 20% annually)
• "It varies" without specifics

Good answers:

• Low turnover with specific numbers
• Long-tenured team members
• Clear retention strategies
• Plans for continuity if key people leave

Questions about their approach

13. Do you use AI tools? How?

Why it matters: AI is transforming software development. Partners using it well deliver faster and cheaper. But AI without human oversight creates problems.

Red flags:

• "We don't use AI" (falling behind)
• "AI writes all our code" (quality concerns)
• No clear policy on AI use

Good answers:

• Thoughtful integration of AI for acceleration
• Human review of AI-generated output
• Transparency about where AI is and isn't used
• Clear quality assurance regardless of how code is written

14. What's your approach to documentation?

Why it matters: Undocumented systems become unmaintainable. When the original developers are gone, documentation is all you have.

Red flags:

• "The code is self-documenting"
• Documentation is an add-on or afterthought
• No standard documentation practices

Good answers:

• Documentation as part of the development process
• Technical documentation (architecture, APIs, deployment)
• User documentation and training materials
• Knowledge transfer as a project deliverable

15. Why should we choose you over competitors?

Why it matters: This is their chance to differentiate. Generic answers reveal generic thinking.

Red flags:

• "We're the best" without specifics
• Focus only on price
• Can't articulate differentiation

Good answers:

• Specific strengths relevant to your project
• Honest acknowledgment of what they're not
• Focus on outcomes, not just capabilities
• Clear understanding of what makes them different

How to use these questions

Don't just read the answers — observe how they respond.

Good signs:

• Thoughtful, specific answers
• Willingness to say "I don't know, let me find out"
• Questions back to you (shows engagement)
• Honesty about limitations

Warning signs:

• Vague, sales-y responses
• Defensive reactions to tough questions
• Overpromising on everything
• Rushing to close the deal

The evaluation framework

After your conversations, score each potential partner:

A partner who scores well across all categories — not just one — is more likely to deliver successfully.

The bottom line

Choosing a development partner is one of the highest-stakes decisions you'll make. The wrong choice costs time, money, and opportunity.

These 15 questions won't guarantee success, but they'll dramatically improve your odds. They'll help you see past the sales pitch to the reality of how a partner actually works.

Ask them all. Listen carefully. Trust your instincts when something feels off.

The right partner is out there. These questions will help you find them.

Entvas Editorial Team

Helping businesses make informed decisions