Hiring someone to build software is a big decision. Whether it's an internal tool, a customer-facing app, or a system integration, you're investing real money and trusting someone with your business operations.
The problem? It's hard to evaluate developers if you're not technical yourself. Everyone's portfolio looks impressive. Everyone promises on-time delivery. And yet, horror stories abound.
Here are 10 questions to help you separate the pros from the pretenders.
1. "Can you walk me through a similar project you've done?"
Why it matters: Past work is the best predictor of future results. You want specifics — not vague references to "many projects like this."
Green flags:
- They can describe the problem, solution, and outcome clearly
- They mention challenges and how they handled them
- They offer to connect you with the client
Red flags:
- Vague answers ("we've done lots of these")
- Can't discuss details due to "confidentiality" on everything
- No portfolio or references at all
2. "What happens if the project goes over budget or timeline?"
Why it matters: Every project hits bumps. What matters is how they handle it.
Green flags:
- Honest about uncertainty upfront
- Clear change request process
- Willing to absorb overruns caused by their mistakes
Red flags:
- "That won't happen" (it will)
- No process for scope changes
- All overruns are billed to you, no matter the cause
3. "Who will actually be working on my project?"
Why it matters: Some shops bait with senior talent and switch to juniors after signing.
Green flags:
- You meet the actual developers
- Clear about team structure
- Consistent point of contact
Red flags:
- "Our team will handle it" with no names
- Developers introduced only after contract
- Offshore handoff you weren't told about
4. "How do you handle communication and updates?"
Why it matters: Radio silence during a project is terrifying. You need to know what's happening.
Green flags:
- Regular check-ins (weekly at minimum)
- Access to project tracking (Trello, Linear, etc.)
- Responsive to questions
Red flags:
- "We'll reach out when there's something to show"
- No project management tool
- Long response times during sales (it gets worse after)
5. "What do you need from us to succeed?"
Why it matters: Good developers know software projects are collaborative. They'll need your input, decisions, and feedback.
Green flags:
- Clear about required time commitment
- Specific about what decisions they need from you
- Realistic about dependencies
Red flags:
- "Just sign off and we'll handle everything"
- No discovery process
- Don't ask questions about your business
6. "How do you handle bugs and issues after launch?"
Why it matters: Software always has bugs. What's the plan when they surface?
Green flags:
- Warranty period included
- Clear support/maintenance options
- Bug vs. feature distinction explained
Red flags:
- "There won't be bugs" (lie)
- Everything post-launch is billable
- No support offering at all
7. "Will we own the code?"
Why it matters: You're paying for this. Make sure you own what you're buying.
Green flags:
- Full ownership transfers on payment
- Source code delivered
- Documentation included
Red flags:
- They retain ownership
- "Licensed" to you (not owned)
- Proprietary framework lock-in
8. "What happens if we want to make changes later — with someone else?"
Why it matters: You might outgrow them, or they might disappear. Can another developer pick up the work?
Green flags:
- Standard technologies and frameworks
- Clean, documented code
- No vendor lock-in
Red flags:
- Custom/proprietary everything
- "Our platform" that only they can modify
- Dismissive about handoff scenarios
9. "Can you explain your pricing?"
Why it matters: You should understand what you're paying for. Vague pricing hides surprises.
Green flags:
- Transparent breakdown
- Fixed price or clear hourly estimates
- Explains what's included and what's not
Red flags:
- "It depends" with no further detail
- Hidden costs revealed later
- Unwilling to commit to any estimate
10. "Why should we choose you over [competitor / doing it ourselves / off-the-shelf]?"
Why it matters: Honest developers will tell you when they're not the right choice.
Green flags:
- Acknowledges alternatives exist
- Clear about their strengths and limitations
- Helps you make the right decision, even if it's not them
Red flags:
- Trashes all competitors
- Can't articulate their differentiation
- Pushes you toward custom when simpler solutions exist
The Meta-Question
Beyond specific answers, pay attention to how they answer:
- Do they listen, or just pitch?
- Do they ask smart questions about your business?
- Do they admit when they don't know something?
- Do you feel like a partner or a transaction?
The best developers are collaborators. They want to understand your problem, not just build to spec.
Next Steps
If you're evaluating developers and want a second opinion, we're happy to chat — even if you don't end up working with us. Sometimes an outside perspective helps.
[Contact us →]
Pink Lemon8 is a Winnipeg-based software development company. We build internal tools, custom systems, and technology solutions for businesses who want things done right.