Choosing a software vendor is one of the higher-stakes decisions a business makes. Get it right, and you gain a partner who accelerates your operations. Get it wrong, and you’re left with a half-built system, a strained budget, and months of lost momentum.
The proposals all look professional. The demos all seem impressive. The difference between a good partner and a costly mistake often only becomes clear after you’ve signed.
These seven questions help you see that difference before it’s too late.
1. What Does Your Discovery Process Look Like?
Discovery is where a vendor learns your business well enough to build something useful. It involves stakeholder interviews, process mapping, technical assessments, and requirements validation.
If a vendor jumps straight to quoting without a structured discovery phase, they’re guessing. That guess becomes your problem later.
2. How Do You Handle Scope Changes?
Requirements change. That’s reality. The question is whether your vendor has a clear process for evaluating changes, communicating impact, and adjusting timelines and budgets accordingly.
“We’ll figure it out when we get there” isn’t a process. It’s a recipe for disputes.
3. What’s Included in Post-Launch Support?
Launch day isn’t the finish line. The first 90 days after go-live are when real users find real problems that testing missed.
Clarify exactly what support is included. How long does it last? What response times are guaranteed? Are bug fixes included or billed separately? What about minor enhancements?
4. Can I Speak with a Similar Client?
References matter, but relevance matters more. A vendor who built an e-commerce platform may not be equipped for your logistics management system.
Ask to speak with a client who had similar requirements, a similar scale, or similar constraints. Hesitation here is a signal.
5. What Happens If We Want to Leave?
Vendor relationships don’t always last forever. You need to understand the exit path before you enter.
Will you receive the full source code and documentation? Are there proprietary frameworks that create lock-in? Can another developer reasonably take over the project?
6. How Do You Handle Disagreements?
This question often surprises vendors, but it’s important. Every project hits friction at some point. What matters is how it gets resolved.
Ask about their escalation process. Ask about past disagreements and how they were handled. A vendor who can’t discuss conflict constructively probably can’t manage it constructively either.
The Conversation Matters as Much as the Answers
Pay attention to how vendors respond, not just what they say. Confident, specific answers suggest experience. Vague or defensive responses suggest gaps.
The right vendor won’t be threatened by tough questions. They’ll welcome them as a sign you’re serious about getting this right.
Tyne Solutions builds custom software for businesses across Asia-Pacific and Europe. If you’re evaluating vendors and want a second opinion, get in touch.