What to ask before buying new business software

Technology evolves quickly. If you’re thinking about upgrading or purchasing new business software, it’s important to make an informed decision. Here’s a list of key questions to ask, both internally and to the provider, before making your investment.

Questions to ask yourself

What are your core needs? List the challenges the software should solve and divide them into:

  • Needs: Must-have features essential for your operations
  • Wants: Nice-to-have tools that make life easier but aren’t critical

What is your budget? Calculate your total cost, including:

  • Software purchase or subscription
  • Any new hardware
  • Implementation or training fees
  • Ongoing support and maintenance

Tip: Cloud-based systems can save money by removing the need for servers and IT staff.

What benefits will the software deliver? Quantify the impact. For example:

  • Will it save you time or reduce errors?
  • Can you reduce contractor or consultant hours?

Try to assign a dollar value to the benefits.

What works well for others in your industry? 

  • What systems are others using successfully?
  • Are competitors switching to something new? Why?
  • What do businesses of your size recommend?

What’s involved in data transfer? Inquire about the following:

  • Can your existing data be imported?
  • Does the provider offer import support?
  • Are there templates or tools to make this easier?

Additional tips:

  • Narrow your choices to 3-4 suppliers
  • Involve staff who will use the system
  • Set a timeline for evaluation and rollout
Questions to ask the provider

How is pricing determined? Common pricing models include:

  • Per Seat: Charges based on the number of individual users.
  • Per Concurrent User: Limits how many users can log in at once.
  • Per Processor: Charges based on the number of computers or servers running the software.

What services are included in the price? Ask if training, customizations, and installation help are included. For local providers, on-site support should be part of the package.

Is there a satisfaction guarantee or refund policy? Before you commit:

  • Ask about the return policy
  • Clarify how many days you can trial the software
  • Get refund conditions in writing, especially for custom software

How are bugs and issues handled? Some providers release fixes regularly, while others only do so when customers report issues. So, you should ask:

  • How quickly are bugs addressed?
  • Is there a support plan or escalation process?

How often is the software updated, and will you be notified? Make sure you:

  • Receive regular updates
  • Are notified proactively, ideally via email (this way you can refer back to the information)
  • Can include multiple contacts in communications

What are the support hours and procedures? Before hiring a software company by purchasing their product, find out where the company is located and if the company has a “passive” or “active” customer support system. Follow up with pointed questions such as:

  • Will you only return my call at certain hours of the day?
  • Will I have to leave messages and wait by the phone for your callback?
  • Will I have a direct call back from a representative, or will I be reassigned to someone different every time I call?
Need further assistance?

You have questions or need personalized support? Our Business Advisors are here to help:
1-833-568-2342 | hrnow@cfib.ca

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