Seven questions to ask any IT vendor before you sign
Most IT projects don’t fail because the technology was wrong. They fail because the relationship between the business and the vendor was set up badly from day one — vague scope, unclear ownership, mismatched expectations, and no exit plan.
Before you sign anything — whether it’s a software licence, a cloud service, or an implementation contract — ask these seven questions. The answers will tell you a great deal about who you’re about to commit to.
1. “Who, specifically, will be working on our account?”
Vendors often pitch with senior people and deliver with junior ones. Ask for the names, the roles, and the percentage of their time committed to your project. Get it in writing.
2. “What does the cost look like in year two and year three?”
Most contracts have a year-one price that’s significantly cheaper than the steady state. Ask for the total cost of ownership over three years — including licences, support, escalation clauses, and any per-user or per-transaction fees.
3. “What happens if we want to leave?”
Every vendor relationship eventually ends. The question is whether ending it will be straightforward or painful. Ask:
- Can we export our data, in a usable format, on demand?
- Are there any termination fees?
- How long does the transition out take?
If the vendor hesitates on any of these, that’s the answer.
4. “How do you handle changes to scope?”
Ask the vendor to walk you through their change-request process. A vendor with a clear, written change process is one who has been through the experience of scope creep before — and learned from it.
5. “What does your support actually look like?”
“24/7 support” can mean a real engineer answering the phone, or a chatbot that takes 14 hours to escalate to someone in another time zone. Ask for:
- The actual support hours
- The first-response and resolution SLAs
- An example of a recent ticket and how long it took to close
6. “Who owns the integrations?”
Most software doesn’t live in isolation — it talks to other systems. Get a clear answer on who owns each integration: the vendor, you, or a third party. The grey areas are where projects collapse.
7. “Can you put us in touch with two reference customers?”
Not testimonial quotes on the website — actual customers, contactable, in roughly your size and industry. A vendor who can’t or won’t provide references is telling you something.
None of these questions are difficult. The reason they’re rarely asked is that the buyer is usually focused on whether the product works, and forgets to ask whether the relationship will. Both matter equally.
If you’d like an independent voice in the room before you sign with a vendor, Zaitoon’s IT consulting division offers contract and proposal reviews as a short, fixed-price engagement. Talk to us.