How to Choose Business Software


Buying new software for your business is much like buying a house. It will have a tremendous impact on your day-to-day. Buy the right one and you’ll enjoy it everyday, but choose the wrong one and you’re in for a bumpy ride.

Make the best decision for you and your organization by keeping these seven things in mind when you’re evaluating new software:

1. Investment

Your software is an investment in your business’ future. When you make this move, you’re investing in a tool that will become the backbone of your organization.

  • Understand what you are willing to pay.
  • Don’t let yourself get sticker shock.
  • Prepare for the potential costs and understand their ROI.

2. Identify Who, How, Where, When

  • Who is going to use the software? Your mom? Your 16-year-old staffer? Your clients? Will they need training? Will you lose any clients because of the change?
  • How are you going to use the software? To manage everything, or just one specific task?
  • Where are you going to use it? On the go, at a desk, near a pool?
  • When are you going to make the switch? Are you looking long-term, or do you need to make a change right away?

3. What’s the value/benefit of making the change?

  • Are you saving time?
    1. Streamlining processes or improving efficiency
    2. Answering people’s questions (support)
  • Filling out paperwork
    1. Following up on client tasks
    2. Improving organization
  • Are you saving money?
    1. Eliminating multiple services
    2. Identifying missed payments
  • Are you improving customer experience?
    1. Making their interactions easier
    2. Providing consistency

4. Define Priorities

Just as you would with buying a house, take time to write out what you need. Making this list will help you as you evaluate your options. Start with the ‘Must Haves’ before you create the ‘Give Up’ list. While getting the perfect software is always the goal, it’s more than likely there will be a few ‘Give Ups’ along the way. Plan ahead for the features and functionality you’re willing and not willing to give up. For example:

  1. Must Haves:
    • Clients need to manage their schedule.
    • Automate billing process.
    • Ability for customization.
  2. Give Ups
    • Processes or workflows.

5. Quality

When it comes to software, understanding the reliability or quality of it is important. Just like you would consider the builder’s reputation for a house, you’ll need to consider the reputation of a software company. If it has all the bells and whistles, but can’t be counted on to work when you need it, you’re wasting time and money.

  • Does it work?
  • Does it work with the hardware you use?
  • Is the software flexible? Is it able to adjust as you grow and to your business needs?

6. Listing Price

Price is an important piece of the decision-making process. It’s key in determining what is possible for your business. There is no use looking at the mansion if you can only afford the one-bedroom rental. Remember that like a house, cheaper does not mean better and it’s an investment in the future of your business. Understand what is included in the price. No one likes surprises — make sure you know what the costs are in these areas:

  • Support
  • Integrations or additional features
  • Onboarding
  • Initial or one-time fees

7. Location

Do you care if the grocery store is around the corner or if a school is nearby? The integrations with other software is just as important. Go back to your original ‘Must Have’ list to see if integrations fulfill some of these needs.

  • What other software do you use in your day-to-day that matter?
  • How well will they work in concert?
  • Which will the new software eliminate?

Other Tips:

  • Leverage the free trial (really use it — test your processes).
  • Set expectations with sales reps by communicating timelines.
  • Think mobile. Can you use it wherever you need?
  • Understand who owns the data. If you ever need to leave, will you be able to get your information? Is there a large fee for getting your data back? Warning: They won’t want to tell you this. You’ve got to ask.
  • Don’t be afraid to negotiate


Cassandra Schwartz is the senior manager of product marketing at Front Desk. When she’s not helping business owners run their organizations better she enjoys exploring. An avid hiker and backpacker, Cassandra spends her free time in search of remote lakes and mountain tops. For more information, download this free Software Buying Checklist to be an informed buyer, call 855.417.7120 or email