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Strategy · 13/06/2026 · 9 min read

What every CEO asks: 7 questions before signing a software contract

A bad software vendor does not just cost you the project fee. It costs you a year of time and your board's trust in any further IT investment. So when choosing, do not test the portfolio — anyone can show you that. Test the answers to seven questions where weaker vendors start talking about an individual approach.

1. Why do you publish your prices?

In the software business a “custom quote” is often just a test of how much the client can bear. A public price saves time for both sides: you know whether you are in budget, the vendor knows they are talking to a serious buyer. Whoever hides their rates usually has a reason — and you are the one who pays for it.

2. What happens if you miss the promised KPIs?

A promise without a penalty is just marketing. A professional defines measurable KPIs in the Discovery phase and puts a clause in the contract: if they are missed, an agreed percentage of the price is refunded. The vendor carries the risk, not you. If someone guarantees the result only verbally, they guarantee you precisely nothing.

3. Who owns the code?

You do — and it should hold from day one. You get repository access immediately, and once fully paid you own all the code and documentation. No vendor lock-in, no hostage-taking the day you decide to leave. The question “what happens when I want to leave you?” is the best litmus test of a vendor's motivation.

4. How fast can you start?

We can start an audit of the current state within 48 hours of getting access. Development typically begins within two weeks of signing — and the exact date is part of the written quote, not a verbal promise. A vendor who cannot tell you when you will see the first working output probably will not show it to you for a long time.

5. Can you build on our existing system?

Yes, and it is our speciality. We modernise legacy systems with zero downtime — strangler pattern, module by module — and integrate with ERP, CRM, accounting and custom internal systems. A “weekend switch” is roulette with the company as the stake; the safe road takes longer, but production never stops for an hour.

6. What happens if something breaks after launch?

The first three months of support are included in every project — monitoring, fixes and minor tweaks. After that you pick an SLA matching how critical the system is. Critical bugs are fixed within four hours, not “in the next sprint”. Fear of being abandoned after payment is the most common reason a CEO delays signing; that is why it belongs in the contract, not in an e-mail.

7. How do you handle security and our data?

We sign an NDA before the first meeting. Your data stays in your infrastructure or an EU cloud, access is named and logged, and a GDPR Article 28 data-processing agreement is attached to every contract. For a company with revenue above one million this is not a nice-to-have — it is a precondition without which the conversation does not even start.

Red flags you hear between the lines

The answers matter, but the manner reveals more. “We'll handle that via a change request” to every other question means scope will be flexible — upward. “We don't usually put that in the contract” about KPIs or code ownership means the risk stays with you. And when the price rises every time you mention an integration you hadn't named before, you are not building a partnership but an open tab. A good vendor talks about limits unprompted, before you even ask.

How to use these seven questions in a single meeting

Do not ask them like an interrogation — put them on the table at once and watch which answers come from memory and which become “we'll send that later”. What a vendor has settled in their contract they say instantly; what they improvise, they defer. In thirty minutes you separate the firm that has worked this way for years from the one inventing its rules on your project. That is the cheapest vendor due diligence you will ever do.

A good vendor answers these seven questions from memory and with a smile — they are already answered in the contract. A weaker one starts talking about an individual approach. The difference between them is exactly the twelve months and fifty thousand euros you do not want to lose.

Facing exactly this? Let's talk numbers.

An audit of your current solution within 48 hours — specific figures, no phrases.

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