5 Questions to Ask Any Custom Software Vendor Before Hiring

The custom software industry has a wide quality spread. Some shops ship reliable software on time and on budget. Others quote 3 months and deliver in 12 (if at all). The 5 questions below are designed to surface the difference in a 30-minute call, before you've signed anything.

1. What's in your "out of scope" list?

A vendor who can write a clear out-of-scope list has done discovery seriously. A vendor who says "we'll handle whatever you need" hasn't — and you'll pay for it in scope creep, missed deadlines, and surprise invoices.

What good answers look like:

"Out of scope for v1: payment processing for refunds, multi-language support, custom reporting beyond the 6 we agreed on, integration with [system you didn't mention]."

Specific items, named systems, clear distinction between "v1 includes" and "future phase."

What bad answers look like:

"We'll discuss that during development."

"Whatever you need."

Vague references to "additional scope" without specifics.

2. Show me a recent project similar to mine

Not testimonials. Not generic portfolio screenshots. A specific, recent, similar project.

What good answers look like:

Walks you through a real client project. Shows the live software (or close-to-live). Discusses tradeoffs they made. Mentions specific challenges and how they handled them.

Says "we built X for Y client in Q3 — here's what we learned that applies to your project."

What bad answers look like:

"We've done dozens like that."

Generic case study with no specific names or numbers.

"We can't share specifics for confidentiality reasons" — every project? Really?

3. What's your weekly demo cadence?

The right answer is: every Friday (or some consistent day). The wrong answer is "we'll demo at milestones."

Weekly demos = misalignments caught at week 2 instead of week 12. Milestone demos = you discover at the milestone that things drifted three months ago.

What good answers look like:

"30-minute demo every Friday at 4pm. You see the actual software running, you give feedback in the same call, adjustments happen the next week."

"Working software is the unit of progress, not documentation or slide decks."

What bad answers look like:

"We'll demo at milestones."

"We send you weekly status reports."

"The full demo is at launch."

4. Will I get the source code, and what does ownership actually look like?

The right answer is: yes, you get a private repository with full history, admin rights transferred to you, and a license that says you own the source code and can modify, deploy, sublicense, and distribute without restriction.

Watch for these caveats:

"Yes you own it, but we keep the framework/foundation/library that runs it"

"Yes but it needs our cloud platform"

"Code is in escrow" (read the trigger conditions carefully — they usually don't fire when you need them to)

If any of these come up, ownership is partial at best. See our deep dive on Source Code Ownership for more.

5. What's your exit story if we want to take this in-house?

This is the question that separates shops that depend on lock-in from shops that don't.

What good answers look like:

"Quick. We hand over the code, deployment scripts, credentials for third-party services. We document the architecture. We're available for 90 days of technical questions. After that you're on your own with documentation that lets you maintain or extend it."

Specific transition plan, specific timeline.

What bad answers look like:

"Why would you want to do that?"

"We'd work with you on that" (without specifics)

"That would require additional contract work."

A bonus question if you have time

Ask: "Tell me about a project that went badly. What happened and what did you learn?"

Every dev shop has had projects go badly. Vendors who can speak openly about a failed project (and what they learned) have institutional learning. Vendors who claim every project went smoothly are either lying or new.

If you want to ballpark cost for your specific scope before hiring anyone, our cost calculator runs 5 questions in 60 seconds. Or contact us for a 48-hour scope conversation — no commitment.