How to Choose a Custom Software Developer: The 10 Key Questions

You have a clear idea for software, but you’re wondering how to choose a custom software developer who can genuinely transform your business?

You may have even tried working with a solo developer, but the project stalled. You realized your ambition exceeded the capabilities of a single person. This is more common than you might think.

Choosing a custom software developer isn’t like selecting an ordinary vendor. It’s a strategic decision that will have a direct impact on the success of your project. Here are 10 essential questions to help you choose a custom software developer wisely and avoid costly mistakes.

How to choose a custom software developer: what you should really evaluate

Choosing a custom software developer starts with assessing their ability to turn your needs into a clear, realistic and structured plan. Before you even look at technologies or working methods, you need to verify whether this partner truly understands what you’re trying to achieve.

A good developer or team should be able to restate your goals, identify fuzzy areas and help you refine your vision. This first filter determines the quality of the entire collaboration, which is precisely why the questions to ask are the following:

1. Are my needs clear and well understood?

Ask yourself this before you even contact a developer. If your vision is vague, expect misunderstandings, cost overruns and missed deadlines. A good partner won’t just wait for your instructions; they will help you clarify them.

A telling sign of a strong partner is their ability to restate your project after the first meeting. If they can summarize your objectives and vision coherently, that’s proof of their understanding. A partner who invests time to define a detailed requirements document with you is a valuable ally, not an unnecessary expense.

2. Is it a freelancer or a team?

This is the crucial question. A freelancer can be excellent for a proof of concept or a simple project. However, as your software becomes more complex, it’s impossible for one person to master every aspect: functional analysis, front-end and back-end development, UX/UI design, project management, quality assurance and cybersecurity.

If you’re aiming for growth and longevity, a multidisciplinary team is essential.

Here’s a comparative table to help you decide:

3. Which technologies are recommended for my project?

Be wary of obscure or niche technologies. Even if they seem performant in the short term, they could become a burden if you struggle to find resources to maintain them in 2, 5 or 10 years.

A good partner will recommend popular, proven technologies, but above all they should justify their choice. Ask them why the suggested technology fits your project. Their answer should be tied to your business objectives rather than their personal preferences.

Ready to choose technologies that truly align with your goals? Talk with an expert who will clearly explain the options and their impacts on your project.

4. What is your experience with similar features?

Beware the trap of industry-specific expertise. It’s not always necessary that the developer has worked in your exact sector. For example, an inventory management system built for manufacturing can be successfully adapted for the medical sector.

What’s more important is whether the developer has built similar features (booking systems, payment processing, analytics dashboards). Ask for concrete examples and demos, if possible.

To get a better sense of the team’s know-how, also take the time to review some concrete deliverables, like the projects already delivered to various clients over the years.

5. What is your project management methodology?

A developer who doesn't talk about process rarely meets objectives. Methodology is the skeleton that supports the delivery of your software. Clarify these points:

• Which methodology do you use (Agile, Scrum, Hybrid)? Why is it suited to my project?

• How often will I have demos? A good practice is to present progress every two weeks (sprints).

• How are priorities managed? The process should be clear and transparent.

• Which tracking tools do you use? Jira, Azure DevOps, Redmine and ClickUp are industry standards. They centralize communications, tasks and bug tracking.

6. How do you ensure quality?

Quality assurance is often the weak link in projects that go off the rails. A QA process that amounts to manual tests by the developer alone is a red flag. A mature approach integrates multiple levels:

• Automated testing

• Peer code reviews

• Manual testing by a dedicated tester

• Multi-device testing

• Code coverage of at least 60%

7. What is your approach to cybersecurity?

In an era of cyberattacks, security is not optional. A mature partner should have a clear secure development policy. Questions to ask:

• How do you handle security updates for dependencies? External libraries should be updated regularly.

• Do you follow recognized standards? Such as OWASP (Open Web Application Security Project) best practices.

• How is access to sensitive data controlled? Who has access to development, test and production environments?

• Do you have logging and auditing mechanisms? In case of an incident, you must be able to trace what happened.

Transparency about these practices is an indicator of maturity and professionalism.

8. Is the development done entirely locally?

Outsourcing isn’t a problem in itself, but lack of transparency is. It’s essential to know where and by whom your software is developed. If part of the work is entrusted to freelancers or a team abroad, you need to understand the implications:

• Security and confidentiality: Will your data be handled in a country with less stringent laws?

• Communication: Will the time difference complicate exchanges?

• Quality and control: How does the partner ensure the quality of subcontractors’ work?

A team that develops locally, in Quebec, often offers better cohesion, smoother communication and a better understanding of local business realities.

9. What kind of support do you offer after launch?

Software is not a project with an end date; it’s an asset that lives for years. Launch is only the beginning. A reliable partner should present a concrete support plan:

• Corrective maintenance: Who fixes bugs after launch, and within what timeframes?

• Evolutionary maintenance: How will new features be developed?

• Hosting and monitoring: Does the partner manage the infrastructure and continuously monitor performance?

A developer who doesn’t talk about software maintenance leaves you with a project at risk from day one.

10. Finally, is there chemistry?

Beyond the technical and the processes, software development is a human endeavour. You will collaborate closely with this team for months or even years. Cultural and interpersonal fit is fundamental.

If the connection is strained from the start, it’s unlikely to improve when pressure sets in.

Conclusion

Knowing how to choose a custom software developer is a strategic decision that directly influences your project’s success. Use these 10 questions to ask a custom software developer as a checklist during your meetings. The answers you receive, or don’t, will be the best indicators to find the partner who will turn your idea into a commercial success.

Ready to validate your choices before you get started? Talk with the Exolnet team, who can analyze your project and guide you toward the best development approach.

FAQ

What is the biggest mistake to avoid when choosing a custom software developer?

The biggest mistake is focusing solely on the initial cost. A low-priced freelancer or team may seem attractive, but the hidden costs associated with delays, bugs and lack of support will quickly outweigh the initial savings. Evaluate overall value, including expertise, methodology and long-term support.

Can a freelancer be enough for my project?

A freelancer can be an excellent option for very simple projects, such as a small app or a proof of concept with a limited budget. However, for complex custom software, a multidisciplinary team is almost indispensable to ensure quality and longevity.

How long does a custom software development project typically take?

The duration varies with complexity. A first version can take 3 to 6 months, while developing a full-featured software product can span 9 to 18 months. Development projects are rarely sprints; they’re marathons that evolve over several years.

Do I need technical knowledge to manage a development project?

No, it’s not necessary if you choose a partner with a strong project manager and a business analyst. Their role is to bridge your business needs and the technical jargon. Your expertise is in your business; theirs is in development. A good team will explain technical issues in plain language.