What to Ask a Software Development Company Before You Sign Anything

Most businesses spend more time negotiating the price of a software project than they do evaluating whether the company they're hiring is actually the right partner.

That's understandable. Price is easy to compare. The quality of a long-term working relationship is much harder to assess in a 45-minute sales call.

But here's the thing: for most mid-size businesses, a software project isn't a one-time purchase. It's the beginning of a multi-year relationship. The software will need updates, fixes, and adaptations as your business grows. The team that builds it will know things about your operations that no one else does. Getting it wrong isn't just a budget problem — it's an operational one.

These are the questions that separate the vendors who will genuinely serve your business from the ones who will take the project, cash the check, and become increasingly hard to reach.

Questions About Long-Term Commitment

"What does our relationship look like after the project launches?"

This is the most important question on this list, and the one most businesses forget to ask. A good software partner should be able to describe clearly what post-launch support looks like — specific response times, maintenance schedules, how they handle updates, and who your ongoing point of contact will be. Vague answers like "we'll be available if you need anything" are a warning sign. You need specifics.

"What percentage of your revenue comes from ongoing client relationships vs. new projects?"

A company that survives primarily on new project revenue has a fundamentally different incentive than one that has built a book of long-term maintenance relationships. If most of their income comes from landing new clients, their attention and resources will always flow toward the next deal — not toward you, once you've signed.

"Can you share examples of clients you've worked with for more than three years?"

Any company can claim they care about long-term relationships. Proof is in the actual client tenure. Ask for references from clients they've maintained active relationships with for several years — and actually call those references.

Questions About Their Process

"How do you handle scope changes during a project?"

Scope changes happen on every project. The question isn't whether they happen — it's how the company handles them. A good partner will have a clear, fair process for evaluating and pricing changes. A problematic vendor will either resist all changes (creating a rigid, unworkable project) or add charges without clear communication. Either extreme is a problem.

"Who will actually be working on our project day-to-day?"

This matters more than people realize. Sales and leadership teams often present well. The actual development team working on your project may be entirely different people. Ask to meet the team members who will be hands-on with your work. Ask about turnover. Ask whether you'll have a consistent point of contact throughout the project or whether it'll be handed off between people.

"How do you handle a situation where the project isn't going according to plan?"

The quality of a software partner is most visible when things go wrong — because things will always go wrong at some point. A company that has a clear, honest process for flagging problems and course-correcting is far more valuable than one that promises everything will go smoothly. Listen for transparency and accountability. Be wary of anyone who can't describe a specific time a project hit difficulty and how they handled it.

Questions About Ownership and Risk

"Who owns the code when the project is done?"

This should be non-negotiable: you should own your code. But the details matter. Ask specifically about intellectual property assignment, what happens to any third-party components used in the build, and whether there are any licensing dependencies that could affect your ownership or usage down the road.

"How do you document your work?"

Documentation is one of the most consistently neglected parts of software development — and one of the most important for your long-term protection. If a developer writes undocumented code, you're dependent on them forever, because no one else can understand what's running. Good documentation means you're never held hostage. Ask to see examples of their documentation from previous projects.

"What would it take for another developer to maintain or update this software after you?"

This is the hostile version of the documentation question — and it's worth asking directly. If the answer is uncomfortable or evasive, that tells you something. A company that builds systems only they can maintain has a very different incentive structure than one that builds for your long-term independence.

Questions About Security and Reliability

"How do you handle security vulnerabilities after launch?"

Software security isn't a one-time concern — new vulnerabilities are discovered in underlying technologies constantly. Ask how they monitor for and respond to security issues after a project goes live. If they don't have a clear answer, your software will be running unpatched vulnerabilities within months of launch.

"What is your uptime track record, and how do you handle outages?"

For business-critical software, downtime is a direct business cost. Ask for specifics on their reliability history and their incident response process. A good partner should be able to tell you clearly how they handle outages — including communication timelines and what your recourse is if reliability standards aren't met.

Questions That Reveal Culture

"Tell me about a project that didn't go the way you expected."

Every company has them. How they talk about it — with honesty and accountability or with deflection and blame — tells you everything about who you're dealing with. The best partners own their mistakes and describe what they learned. The worst ones don't have a good answer for this question.

"What would make you walk away from a potential client?"

This one surprises people, but it's genuinely revealing. A development company with standards and integrity will have an honest answer here. They'll describe clients they aren't a good fit for — unrealistic timelines, undefined scope, unwillingness to collaborate. A company that says "we'll work with anyone" is telling you they're optimizing for revenue, not fit.

One Final Question — The One That Matters Most

After you've asked all of the above, there's one last thing to evaluate that no question can fully capture: do these people actually seem invested in your success?

Not in the success of the project as a deliverable. In your business. Do they ask questions about your operations, your goals, your users? Do they push back on ideas that won't serve you well, even at the risk of reducing the scope? Do they seem like they want this to work for you long-term?

The best software relationships aren't transactional. They're partnerships. And you can usually tell the difference before you sign anything — if you're asking the right questions.

At Ontoborn, we work with mid-size businesses, enterprises, and research organizations who need a software partner they can count on for years, not months. If you'd like to ask us these questions directly, we're ready for them.

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Ontoborn Technologies is a custom software development and maintenance company trusted by enterprises, universities, and growing businesses for over a decade. We build software that lasts — and stay with you after launch.