20 Questions to Ask Before Purchasing HR Tech

Oct 12, 2021
hr tech

No matter the size of your business, you will at some point require some type of technology. Excel spreadsheets are great, but can only take you so far…

Whether it be a bookkeeping system, a platform to manage your inventory, or maybe a place to manage your employee information or to complete your payroll, the first step to getting the right tech in place is to ask the right questions.

Asking the right questions:

  • Makes the most of your time in speaking with the software vendor
  • Helps ensure you get the right information to be able to make the best decision
  • Prevents wasted time and money by purchasing the wrong software (ALERT: Sticky Situation!)

Because it is so important to get your technology right, one of our 8 foundational HR pillars under our Monthly HR Subscription -  is all about getting the right HR Systems & Technology. For example, if you are frustrated with patching all your different systems together, like payroll and your HR database and maybe a recruiting and onboarding platform, consider an “all-in-one” software like BambooHR. They get all these things in one place and provide excellent customer service at a price point small businesses can afford.*

In this blog post, we are sharing 20 questions to start you off on the right foot when looking at a software provider.

Here are the questions:

  1. What are the primary functionalities of your platform? (Start with this question to learn what the rep says are the system’s primary capabilities. This way, you are not leading them with telling them your pain points and then having them tell you they will meet your every need…)
  2. Of the functionalities you just shared, which are your top 3 “signature” or best modules/functionalities where you feel you serve customers best?
  3. What sets you apart from other software platforms which offer the same features?
  4. What size business do you best serve (aka what is their “Sweet Spot” customer size)?
  5. How long have you been in operation serving clients?
  6. When is your next scheduled upgrade and what happens during an upgrade on the client end?
  7. Is the system cloud-based or on-premise?
  8. How do you charge?
  9. I want to be sure we are not paying for services we won’t need/use – please share details about how I can ensure this won’t happen.
  10. What are your implementation fees?
  11. What are the costs to integrate with other software platforms?
  12. Which systems do you integrate with? (Ask that they send you a list of systems so you have it when analyzing which platform will be best.)
  13. When can we expect to go live after we sign the contract to start services?
  14. How long do you anticipate implementation to take?
  15. What are typical hiccups you have seen during implementation? (See how honest they are! If they say all implementations are smooth, that can be a red flag which requires more questioning.)
  16. All systems have their flaws - what would users say they like least about your system?
  17. What would users of your system say they like most about your platform?
  18. Do I have the ability to customize the system for my specific business in all areas, some, or not at all?
  19. What does your customer support look like? Do I work with a designated person or is there a team to support me? Do you have chat customer support?
  20. Can you give me 3 names of users I can all to learn more about their hands-on experience has been?


Good luck! 

*Expedition HR is excited to announce our new partnership with . BambooHR is the leading online HR software provider helping small and medium businesses elevate the value of their HR function. BambooHR’s intuitive interface, streamlined implementation process and responsive support team make it an excellent choice for HR software. If you are looking to automate your operational day-to-day HR tasks so that you can focus on the strategic aspect of HR for your company, check them out !

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As a subscriber, you...

  • Receive on-demand HR Consulting and other HR Services for a fraction of the cost to hire a full time HR employee
  • Have the support and knowledge to deal with workplace conflict
  • Know exactly what phrasing to use for tough conversations with your employees
  • Have extra time in your day because you have immediate access to the right HR forms, checklists, and tools (no more Googling HR forms!)
  • Have an expert to guide you with how to fire someone when the need arises
  • Know how to better manage employee performance
  • Understand HR Compliance
  • Have peace of mind

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