8 Questions to Ask During a Software Vendor Reference Check (2026)
When you are about to sign a software contract, the vendor’s own customers will tell you more than any demo or sales deck. A reference check, calling companies that already use the software, is the most reliable way to find out how a product performs in the real world, how the vendor behaves after the sale, and what surprises to expect. The catch is that most buyers rush it or ask soft questions. Here are the questions that actually matter in 2026, and how to run the calls so you get honest answers.
Key takeaways
- The reference check is one of the most valuable steps in choosing software, because it is the only view of what happens after the contract is signed.
- Ask for references in your industry and of your size, and insist on speaking to real users, not just the executive who signed the deal.
- Cover implementation, training, support, real cost, security, and results, and always ask the two questions vendors dread: what went wrong, and would you buy it again.
- Watch for a curated list, reluctance to connect you, and answers that sound rehearsed. Those are signals in themselves.
Why the reference check matters so much
A sales team shows you the software at its best. A reference customer shows you the software as it actually runs, months or years in, with real data and real users. Nobody can tell you more about how a vendor does business than the people who have already lived through implementation, support tickets, and a renewal. Skipping or rushing this step is how buyers end up surprised by hidden costs, a painful rollout, or support that vanishes once the ink dries.
Set the calls up right
Before you dial, get the reference list from the vendor and check it critically. You want companies in your industry, or at least with similar size and challenges, not just the vendor’s three happiest marquee accounts. Ask to speak with more than one person per reference: at least one hands-on user from each department that will use the software, plus someone from IT who oversees it. The signer of the deal and the daily user often have very different opinions, and you want both.
The questions to ask
1. How did the implementation go?
Ask how smooth the rollout was, how long it took, and whether the system connected cleanly to their existing tools. Implementation is where good software goes bad, so probe for delays, scope creep, and integration headaches.
2. How long did it take to get your team productive?
Training time is a real cost. Ask how long it took before staff were genuinely productive, not just logged in, and what the learning curve was like for non-technical users.
3. How much did the vendor help, and how good was it?
Find out whether the vendor actively supported the rollout, and how. A vendor that hands you the keys and disappears is very different from one that helps you succeed. Ongoing responsiveness matters as much as the initial onboarding.
4. What has gone wrong?
Ask directly about bugs, outages, and problems, and how the vendor handled them. Every product has issues; what you are measuring is how the vendor responds when they happen. A reference who cannot name a single problem is either lucky or not being candid.
5. Did people actually adopt it?
High adoption is the truest sign that software works. Ask what share of intended users actually use it daily and what the feedback has been on ease of use and functionality. Shelfware is expensive, and low adoption is a warning.
6. What did it really cost?
Go past the license price. Ask about implementation fees, add-ons, per-user charges, and especially what happened at renewal, since introductory pricing often jumps. Ask whether any costs surprised them. This is where buyers get burned most often.
7. How are security, data, and reliability?
This question barely existed when reference checks were first written about, and now it is essential. Ask about uptime and outages, how the vendor handles security and compliance, whether the reference has hit any data or privacy issues, and how easy it would be to get their data out if they ever left.
8. What results have you seen, and would you buy it again?
Ask what measurable return they have gotten and whether it matched what the vendor promised. Then ask the single most revealing question in any reference check: knowing what they know now, would they buy the same software again? The pause before the answer tells you as much as the answer.
Red flags to watch for
The reference process itself is data. Be wary if the vendor drags its feet on providing references, offers only a tightly curated few, or will only let you talk to an executive rather than daily users. Rehearsed, uniformly glowing answers are a flag too. And if you can, find a reference the vendor did not hand you, through your own network or a peer community, because an unscripted customer is often the most honest one you will talk to.
Frequently asked questions
What is a vendor reference check?
It is the step in software selection where you speak with a vendor’s existing customers to learn how the product and the company perform in real use, covering implementation, support, cost, and results before you commit.
How many references should I check?
At least three, and ideally including one you source yourself rather than only the vendor’s list. Within each, try to speak with both a daily user and someone who owns the relationship or the IT side, since their views often differ.
What is the most important question to ask?
“Knowing what you know now, would you buy it again?” It forces an honest overall judgment. Pair it with “what has gone wrong and how did the vendor handle it,” because how a vendor responds to problems predicts your own experience.
Should reference customers be in my industry?
Ideally yes, or at least similar in size and needs. A reference that looks like your business faces the same integration, compliance, and workflow issues you will, which makes their experience far more relevant than a marquee logo from a different sector.
The verdict
A good reference check is the cheapest insurance you can buy before a software purchase. Line up references that look like your business, talk to the people who actually use the product, and ask about implementation, training, real cost, security, and results, then close with the question that cuts through everything: would you buy it again? Do that and you will walk into the contract knowing what the demo could never tell you.
Sherman Hsieh
Independent analysis of enterprise software — ERP, CRM and more
