Software Buying Tips

25 Critical Questions for Software References

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I have a secret that will free up weeks of your time.  Interested?25 critical questions references

Do you remember reading Good to Great?  Remember the idea of getting the right people on the bus?  Do you remember what Jim Collins wrote about hiring the right people?

He mentioned that good-to-great leaders take “the time to make rigorous A+ selections right up front.”  He included a quote from the then CEO of Gillette, Colman Mockler, “Every minute devoted to putting the proper person in the proper slot is worth weeks of time later.”

So, what’s the secret to saving weeks of your time?

Simply to take the time to select the proper person…or software in this case.  Do it right up front.  Follow a proven process and don’t skip the references (current customers with a fully installed, recent version of the product).

Below are a few tips and some suggested questions to ask when talking to a customer reference.  Remember, talking to customers gives you a greater assurance that the software can successfully perform as you need it to and, ultimately, save you weeks of time later.

Tips for Talking to Customer References

  • Pick customers that are similar to you (industry, size, customer base, geography)
  • Relate your questions to your business and processes
  • Talk to at least one user in each functional department, including IT
  • Don’t evaluate information while you are gathering it, evaluate afterwards
  • Focus on examples and facts rather than people’s opinions

25 Critical Questions to Ask Customer References

Background Questions

  • What is your company’s relationship with the vendor?
  • Do you receive anything for being a reference?
  • Describe your business and how you operate.
  • When and why did you decide to look for (type of software) software?
  • What other systems did you consider when making this decision?

Product Questions

  • Why did you choose this system?
  • How does the system perform vs. expectations?
  • How does the system perform with regards to (your critical processes)?
  • What are the best features and limitations?
  • What feedback have you gotten from the users?
  • Did you have to customize the system?  If so, why/how?
  • Is there anything that surprised you about the system?
  • What significant benefits have you realized since implementing the system?

Implementation and Support Questions

  • Describe the implementation project and team.
  • How long did it take to implement the system?
  • What tasks were you responsible for completing during implementation?
  • Describe the technical support process.  How do you submit issues, receive help, etc…
  • How responsive is the vendor to issues?
  • What is the quality of support?
  • What training was provided/is available?

Wrap-up Questions

  • What was the total cost of ownership (software, hardware, services, training, etc…)?
  • What would you do differently with regards to selection or implementation?
  • What has the return on investment (ROI) been so far?
  • Would you select this vendor/system again?
  • Is there anything else you can share that may help us make a decision?

P.S. Product reviews are available in the Capterra directories.  Check to see which vendors have customer reviews online.  Want more info on the power of reviews, check out Alexandra’s post, “Consider the Source“.

About the Author

Ryan Yeoman

Ryan Yeoman

Ryan Yeoman currently resides in the always sunny Cabo San Marketing neighborhood at Capterra working with a great team to help software buyers find the right software. He's inspired by his two sons, the mountains, and Life is Good T-shirts.



Comment by JP Medved on

Hi Jennifer, while we get that link up and running again, you can check out a similar guide here:

Comment by Jennifer Chien on

Great resource! The proven process link is not working. Would it be possible to get a new link? Thank you!

Pingback by Capterra Blog – A blog about business software - Stretchy Software: ChMS that Grows with Your Small Church – on

[…] option measures up to the others. Read reviews of the software you’re considering and actually call current users to see how the software works in real life. Look at the company’s website and ask if there’s a […]

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