Choosing a software development company is harder than it should be. Websites are polished. Case studies are cherry-picked. Promises are easy to make. By the time you discover a company can’t deliver what they claimed, you’re already mid-project and the cost of switching is high.
After 20 years on both sides of this relationship — building software for clients and helping clients evaluate options — here’s what I’ve learned about what actually matters.
The Team Question
The most important question is: who actually does the work?
Many development companies make sales with senior developers and deliver work with junior developers. The person you meet is not the person who writes your code. By the time you realize this, you’ve paid for the relationship.
Ask explicitly: who will be the primary developer on my project? Can I talk to that person before we sign a contract?
If they can’t tell you, or if the person they name can’t speak in detail about your specific project — that’s a signal.
Track Record in Your Domain
General software development skill doesn’t automatically translate to solving your specific type of problem. A company that’s excellent at SaaS consumer apps might be wrong for a manufacturing operations project.
Ask for case studies or references in your industry or for your type of problem. Not just “we’ve built software before” — specifically relevant experience.
When you talk to references (and you should talk to references, not just read testimonials), ask:
- Did they deliver what they said they would?
- How did they handle problems when they came up?
- Would you hire them again?
- What did they get wrong?
Process Transparency
A development company that can’t explain their process clearly doesn’t have a consistent one. That means inconsistent quality.
Questions to ask:
- How do you handle requirements changes mid-project?
- What does the testing process look like?
- How do you communicate progress?
- What happens if the project goes over scope?
Red flag: vague answers that could apply to any project. Green flag: specific answers that reflect experience with real projects.
Pricing Transparency
Development companies that won’t discuss pricing until after extensive discovery calls are either uncomfortable with their pricing or using the discovery process to qualify you. Both are legitimate reasons for their approach; neither serves you well.
Ask for a ballpark range before committing significant time. A good development company can tell you that a project of your type and scale typically runs $X-$Y, with the caveat that exact pricing requires understanding your requirements.
If the range they give you has the upper bound more than 3x the lower bound, they either haven’t done similar projects or are hedging extensively. Neither is great.
Size and Structure
Large agencies have overhead. Account managers, project managers, sales teams, executive time — all of this costs money that comes from your budget without directly contributing to your software.
Smaller shops and individual developers have less overhead, which means more of your budget goes to actual development. The tradeoff is capacity and continuity risk — what happens if the one developer is sick, or leaves, or gets busy with another project?
For mid-market businesses, my experience is that small, focused shops deliver better value than large agencies for most projects. The key is finding ones that have the depth to handle your complexity.
Communication Style
Software projects require ongoing communication. Bad communication is the root cause of most project failures.
In discovery conversations, pay attention to:
- Do they ask more questions than they answer?
- Do they push back on unclear requirements?
- Do they explain technical concepts clearly?
- Do they seem interested in your business problem or just the technical implementation?
The developers who ask good questions are the ones who’ll build the right thing.
Why I Work the Way I Do
I’m a small operation by design. One developer — me — as the primary on every project, with a network of trusted specialists for specific needs. No account managers, no sales team, no layers between you and the work.
This means: the quality is consistent because I’m accountable for it. The communication is direct because there’s no intermediary. The estimates are accurate because I’m the one doing the work.
It also means I have finite capacity. I’m selective about projects because I can only take on so many at once. I’d rather do fewer projects right than more projects wrong.
If you’re evaluating development options and want a direct conversation about whether I’m the right fit, reach out. I’ll give you an honest answer.