Choose a custom software development company by testing how it thinks, not how it pitches. Shortlist three firms, ask each the same 15 questions about your business, their process, code ownership, security and support, then score the answers side by side. The company that asks you the sharpest questions back is usually the safer bet.
This post gives you those 15 questions, explains why each one matters, and shows what a good answer and a worrying answer sound like. If you want the wider picture first (what custom software is, when it is worth it and how projects run), our guide to custom software development for growing businesses covers it.
What should you prepare before you speak to anyone?
Prepare a one-page brief and a budget range. Without them, every agency will quote a different imaginary project and you will have nothing to compare.
Your brief does not need to be technical. It should cover:
- The problem in business terms. "Our sales team loses track of enquiries between WhatsApp, email and the website form" is more useful than "we need a CRM".
- Who will use it. Staff, customers, suppliers, or all three.
- What it must connect to. Accounting software, payment gateways, your website, ad platforms.
- Your deadline and why it exists. A trade show date is a real constraint; "as soon as possible" is not.
- A budget band. Agencies can only suggest sensible trade-offs if they know the ceiling.
If you want to go further, turn that page into a short requirements document listing each user type and the three or four things they must be able to do.
Which questions show whether they understand your business?
These first four reveal whether the company will build what you need or simply what you asked for.
1. "What would you need to know before you could give us a firm price?" A strong company lists specifics: user roles, integrations, data volumes, edge cases. A weak one gives you a number on the first call. Instant quotes on vague briefs either hide large contingency margins or lead to change requests later.
2. "What would you leave out of version one, and why?" You are looking for a partner who protects your budget by cutting scope. If they agree to build everything on your wish list, they are either not thinking or planning to bill you for it later.
3. "Have you built something with a similar workflow, even in a different industry?" Industry match matters less than pattern match. A booking flow for a clinic and one for a photography studio share most of their logic. Ask them to walk you through how they solved it, not just to show screenshots.
4. "Who from your side will talk to our team, and how often?" The answer should name a role (project manager, product lead or the developer themselves) and a rhythm, such as a weekly demo. "Whenever you need us" sounds friendly but usually means nobody owns communication.
What should you ask about their process and delivery?
Process questions tell you how the project will feel in month two, when the excitement has gone and decisions get harder.
5. "Do you run a discovery phase, and what do we get at the end of it?" Good answers describe a paid, time-boxed phase that ends with written scope, wireframes, a technical plan and a firm estimate. Our explainer on what a software discovery phase is and why it saves money covers what that deliverable should include.
6. "How will we see progress before the end?" Look for working software shown regularly on a test (staging) site you can log into. Status reports alone are not progress.
7. "What happens when we change our mind about a feature?" Every project changes. The question is whether there is a clear, written change process with cost and time impact agreed before work starts.
8. "How do you test the software?" Expect a mix of automated tests for core logic, manual testing on real devices, and a user acceptance period where your team signs off. "Our developers test as they go" is not enough on its own.
9. "Which contract model do you recommend for this project, and why?" A thoughtful company will explain the trade-offs between fixed price, time and materials, and a dedicated team for your situation specifically. Our comparison of fixed price vs time and materials vs dedicated team contracts will help you judge whether their reasoning holds up.
What should you ask about ownership, security and data?
These three questions protect you if the relationship ends. Skip them and you can end up unable to change your own software.
10. "Will we own the source code, and when does ownership transfer?" The answer should be yes, in writing, usually on payment of each milestone or the final invoice. Ask whether any of their own reusable components stay theirs and what licence you get to use those.
11. "Whose accounts will the code, hosting and domain live in?" Ideally yours: your code repository, your cloud account, your domain registrar, with the agency given access. If everything sits in their accounts, ask how and when it moves to you.
12. "How do you handle security and personal data?" Listen for concrete practices: role-based access, encrypted connections, regular dependency updates, sensible logging, and awareness of the privacy laws that apply to you (such as India's DPDP Act 2023 or Australia's Privacy Act 1988). A good team can also give an example of a real issue they caught. On our own site, for instance, we found and fixed a login rate-limit bypass that came from trusting a spoofable IP header, and removed unsafe-eval from the Content Security Policy. Small, specific stories like that are a better signal than a list of buzzwords.
What should you ask about price, support and the long run?
The last three questions are about the years after launch, which is where most of the total cost sits.
13. "What exactly is included in the quote, and what is not?" Hosting, third-party licences, app store fees, content entry, training and post-launch fixes are common gaps. Get the exclusions in writing.
14. "What does support cost after launch?" As a rough planning figure, annual maintenance tends to run at about 15–25% of the original build cost, depending on how much the software changes. A company that cannot give you any support model is planning to disappear after go-live.
15. "If we wanted to move to another developer in a year, what would you hand over?" This is the most revealing question on the list. Confident firms answer immediately: repository access, documentation, credentials, deployment notes and a handover call. Defensive answers tell you everything you need to know.
How do you score the answers fairly?
Score each company on the same sheet straight after each call, while it is fresh. Use a simple 0–2 scale per question and weight the ones that matter most to you.
| Question group | Strong answer (2 points) | Weak answer (0 points) |
|---|---|---|
| Understanding (Q1–4) | Asks about users, edge cases and integrations; suggests cuts | Quotes on the first call; agrees to everything |
| Process (Q5–9) | Paid discovery, regular demos, written change process, clear testing | "Agile" with no detail; progress shown only at the end |
| Ownership and security (Q10–12) | Code and accounts in your name; specific security practices | Code stays in their accounts; vague on data handling |
| Price and support (Q13–15) | Written inclusions and exclusions; defined support plan; easy handover | Hidden extras; no support model; defensive about leaving |
Weight the ownership and handover questions double. A slightly slower or pricier vendor is a manageable problem; being locked out of your own code is not.
For the warning signs that should knock a company off your list entirely, read our companion checklist of red flags when hiring a software development agency.
How much should a good company charge?
Price alone will not tell you who is good, but it will tell you who is unrealistic. These are typical market ranges we see, shown as estimates in US dollars; real quotes depend heavily on scope.
| Project type | Typical range (USD, estimate) |
|---|---|
| Simple internal tool or automation | $6k–20k |
| MVP web app or SaaS | $15k–50k |
| Custom CRM | $20k–90k |
| Mid-size web platform | $50k–150k |
An MVP usually takes about 8–16 weeks and a mid-size platform 4–9 months. If one quote is far below the others, ask what is missing rather than celebrating. Comparing quotes from different countries? Make sure each one covers the same scope, the same support period and the same handover terms before you compare totals.
Frequently asked questions
How many software companies should I shortlist?
Three is usually right. Fewer gives you no comparison; more than four turns selection into a full-time job and the quotes start to blur together. Ask all three the same questions so the comparison is fair.
Should I choose the company with the most relevant industry experience?
Not automatically. Experience with a similar workflow, such as bookings, approvals or lead routing, often matters more than the same industry. Ask them to explain how they solved a comparable problem and judge the depth of the answer.
Is it a bad sign if a company asks for a paid discovery phase?
Usually the opposite. A paid discovery phase means they want to understand the problem before committing to a price. The warning sign is a discovery phase with no clear deliverable at the end.
Do I need a technical person to run this selection?
It helps but is not essential. The 15 questions are written so a non-technical owner can judge the answers by their clarity and specificity. If the final decision is large, paying an independent technical adviser for a few hours to review proposals is money well spent.
Should I ask for references?
Yes, and ask to speak to a client whose project went through problems, not just a happy one. How a company handled a missed deadline or a scope dispute tells you more than a polished case study.
Ready to put us through the same test?
We are happy to be one of your three. Bring your brief, ask us all 15 questions, and judge the answers against the projects we have shipped and the services we offer. When you are ready, book a discovery call and get a fixed-price quote.