A few years ago, I made the mistake of hiring a software development contractor solely based on their impressive resume. They seemed smart, experienced, and said all the right things. But two months later, I was knee-deep in delays, miscommunications, and a half-broken platform that never quite worked as promised. That experience taught me a valuable lesson: hiring a developer isn’t just about skills — it’s about alignment, accountability, and understanding the bigger picture.
Today, I run a digital agency where hiring developers — for ourselves and our clients — is part of our daily workflow. We’ve now built systems and filters to avoid costly mistakes, and in this post, I want to walk you through what really matters when hiring a software development contractor — things I wish I knew when I was starting out.
The Real Role of a Contractor in Your Business
Let’s begin with clarity. A software development contractor isn’t just a coder. They are a temporary extension of your business. You bring them in to solve a specific problem — whether it’s launching a mobile app, automating internal processes, or scaling your existing platform.
Unlike full-time employees, contractors don’t have long onboarding processes or permanent roles. They’re results-driven professionals expected to plug into your system and deliver. But that also means they must adapt quickly, understand your goals deeply, and be proactive from day one.
Many founders mistakenly assume hiring a contractor is a shortcut. In reality, it’s a high-leverage decision — but only if you choose the right one.
Why Technical Experience Isn’t Enough
I’ve interviewed dozens of candidates who could talk endlessly about React, Node.js, Laravel, or Docker. But technical skills, while necessary, are not the full picture.
The best contractors are those who’ve solved problems similar to yours. If I’m building an e-commerce checkout funnel, I want someone who’s optimized conversions before. If it’s a SaaS dashboard, I want someone who’s built scalable data systems and user management features. It’s not about ticking off tech stacks — it’s about understanding user flows, edge cases, and what happens when things break in production.
I always ask contractors to walk me through their previous projects, not just in terms of code but in terms of the business problem they were solving. That’s where you hear the truth — not just about how they code, but how they think.
How They Communicate Tells You Everything
During one hiring cycle, we had a developer with an amazing portfolio. But within the first week of the project, we couldn’t reach him for three days. When he replied, he claimed he was “just deep in work.” That’s not good enough — especially when a deadline is on the line.
I’ve learned the hard way that good communication is often more important than perfect code. A great contractor sends updates without being asked. They ask questions when something’s unclear. They respect your time, your language, and your process. You can feel the professionalism in every interaction.
When you’re hiring remotely — and most contractors today work remotely — this becomes even more important. A 12-hour time difference isn’t a problem if the communication is strong. But even the same time zone won’t help if they disappear when issues arise.
Problem-Solving Is a Superpower
Code is just the output. But real value comes when a contractor can identify the real issue behind a vague bug report or make smart architectural decisions that save you money in the long run.
I remember once hiring a junior contractor who didn’t have the flashiest portfolio. But during the test project, he found a smarter way to handle a feature that cut our infrastructure cost by 30%. That’s the difference between a coder and a problem-solver.
Ask them how they handle unexpected changes. What happens when the scope shifts mid-project? How do they deal with messy legacy code or API errors? Their answers will tell you whether they can think independently — or whether they’ll stall at the first roadblock.
Don’t Skip the Background Check
Even if everything looks good on paper, I never skip references. A quick 5-minute call with a previous client can tell you more than any portfolio ever could. I usually ask about delivery timelines, responsiveness, and whether they’d hire the person again.
Sometimes, the most talented developers have burned bridges by missing deadlines or being difficult to work with. A reference call saves you from learning those lessons the hard way.
Also, don’t ignore online reviews. Many contractors list themselves on Upwork, Clutch, or LinkedIn — and the feedback there can be eye-opening.
Process Matters More Than You Think
One of the earliest signs of a professional contractor is their process. Do they break work into milestones? Do they use Git or some version control system? Are they familiar with Agile sprints, or do they just “wing it”?
I’ve learned that even talented developers fail without a structure. On the other hand, even average developers who follow a good process can produce solid results. Ask them to walk you through how they approach new projects. You’ll get insight into how they think, how they prioritize, and how reliable their delivery will be.
In our agency, we always clarify expectations around tools and workflows from the start — whether that’s Jira for tracking or GitHub for code reviews. It makes everything smoother.
Security and Legal Clarity Cannot Be Optional
One of our clients once brought in a developer from another agency without a proper contract. The project went south, and suddenly there were disputes about who owned the code. It got messy.
From that point on, we made sure every project started with a clear contract. Ownership of code, confidentiality, payment terms, delivery deadlines — everything must be defined.
Especially if your project handles sensitive user data, ask about their approach to security. Do they follow secure coding practices? Are they familiar with GDPR or local data regulations? Even if you’re not a legal expert, make sure you have basic protection in place — including NDAs and IP clauses.
Can They Scale With You?
One thing I love about working with great contractors is that they often grow into long-term collaborators. You start with one small project, and before you know it, they’re managing bigger parts of your tech stack.
That’s why I always look for someone open to evolving with the project. I ask about their availability for future work, whether they work with a team, or if they’re open to retainer agreements. If your business grows, your tech needs will too — and switching developers midstream is painful. It’s better to build that flexibility in from the beginning.
Be Clear About Cost — But Don’t Race to the Bottom
Budget matters, especially for startups. But I’ve seen too many founders ruin their product by going with the cheapest offer.
Instead of asking “What’s your hourly rate?”, I prefer to ask “How do you typically structure your pricing for this type of project?” Good contractors can break down pricing based on scope, features, and delivery phases. They’re not afraid to talk money because they’re confident in their value.
Always get the payment terms in writing. Clarify what’s included, how revisions are handled, and when payments are due. Trust is great — but clear terms protect both sides.
Trust Your Gut — and Know the Red Flags
There are subtle signs that something might go wrong. If a contractor avoids direct questions, if their answers feel rehearsed, or if they constantly shift timelines — it’s a warning.
I’ve learned that hiring is both science and instinct. After all the interviews and checks, I ask myself: Would I feel confident handing this person the keys to an important piece of my business? If the answer isn’t a strong yes, I move on.
Final Thoughts from a Founder’s Desk
Hiring a software development contractor is a serious decision — one that impacts your timeline, your product quality, and your bottom line. Over the years, I’ve made mistakes, learned from them, and eventually built a playbook that helps me and my team choose with confidence.
My goal in writing this wasn’t just to help you hire a better developer — it’s to save you from painful detours I’ve personally experienced. A great contractor won’t just deliver code. They’ll solve problems, anticipate risks, and help your product thrive.
So take your time. Ask tough questions. And when you find someone who feels like a true partner — not just a vendor — hold on to them. They’ll make all the difference.
