The Ultimate Software Vendor Evaluation Guide for Total Software Dummies

So, you’re thinking about buying some fancy software, huh? You might be tempted to just close your eyes, pick something random, and hope for the best. Well, I hate to break it to you, but software isn’t like picking a mystery box on a game show. You need a strategy, my friend! Otherwise, you might as well throw your money into a pit and set it on fire.

But don’t worry, I’ve got your back. In this guide, we’ll dive deep into the mystical world of software evaluation, where unicorns are real, and spreadsheets are your best friends.

Chapter 1: The Shocking Importance of Software Evaluation

You might be thinking, “How hard can it be to pick software?” Well, my friend, it’s not as easy as ordering a pizza. You see, software is like a long-term relationship. You wouldn’t just marry the first person you meet, right? So, don’t rush into a software commitment without some serious thought.

Things to consider:

  1. Your Business Needs: Figure out what your business actually needs.
  2. Vendor Product Lines: Ensure vendors offer what fits your business.
  3. Future Tech: Look for vendors embracing the future.

Chapter 2: The Software Characteristics Game

Now that you know why software evaluation is the real deal, let’s talk about what to evaluate.

Key factors:

  1. Functionality: Look for AI, speed, and specific features like payroll management.
  2. Training and Support: Ensure your vendor offers a GPS out of the digital labyrinth.
  3. Deployment: Choose between DIY (on-premise) or takeout (cloud-based).
  4. Hardware and Mobility: Ensure your software is as mobile as your favorite sneakers.

Chapter 3: The Price is Right... Or Is It?

You’ve made it this far, and now it’s time to talk money. Brace yourself!

Financial considerations:

  1. Pricing Models: Choose between perpetual license or subscription wisely.
  2. Number of Users: Pay for the seats your software circus tent can hold.
  3. Cost Types: Understand upfront, recurring, and avoided costs.

Now, armed with this humorous guide, you’re ready to tackle the software evaluation maze. Just remember, picking software is like choosing a pet – it’ll be with you for a while, so make sure it’s one you can live with.


In conclusion, embarking on the journey of software selection is no trivial task—it’s a strategic decision with lasting implications for your business. By recognizing the importance of thorough evaluation, considering essential factors like functionality, support, deployment, and pricing, you can navigate the labyrinth of software choices with confidence. Remember, this is a commitment akin to choosing a reliable partner, and with the right insights, you’ll not only avoid the pitfalls but also find software that aligns seamlessly with your unique business needs. So, armed with knowledge and a touch of humor, venture forth into the software landscape, and may your choice be as harmonious as a well-played symphony.


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