May 22, 2024

Evaluating Your Software Tools: How To Guide & Free Template

Not sure if your software is still a good fit for your business? Learn how to evaluate your tech tools, and get our FREE template to help you out.

Time to read:
4 minutes
Written by
Jennifer Cote

Have you ever bought something that you thought would change your life, but then a year later, you never use it? The technology you invest in for your company can be the same. You can choose a CRM or email marketing tool based on what worked for you at the time, but that doesn’t mean it’s still the best fit.

On the flip side, you can also buy something or choose a tool that is your favorite software years and years later! 

On the surface, one is not necessarily better than the other — it’s natural that as your business grows and changes, that the tools you need could too. 

The challenge is when you don’t realize that your tools don’t fit anymore. That’s why it's important to assess and reevaluate your tools and software (also called your “tech stack”) every year. 

Read on to learn:

  • What a tech stack is
  • Why “good software” is subjective
  • Steps to evaluating your software tools
  • FREE template for software evaluation (It’s at the bottom so you can scroll down to it if that’s what you’re looking for)

What is a tech stack?

A tech stack refers to the set of software tools, apps or systems you use to run your business. For small business this could include your payment processor, email tools, website, text messaging tools, customer data management, sales tracking, job tracking, etc. 

Examples of what would be included in your tech stack as a small business are:

  • Payment processor
  • CRM
  • Analytics
  • Email marketing tools
  • Website
  • Calendar tools
  • Job tracking tools
  • Social media tools

In terms of actual names or companies, your tech stack could include:

  • Quickbooks
  • Roofr
  • Google Analytics
  • Squarespace
  • Canva
  • SurveyMonkey
  • Hubspot
  • Calendly
  • Google sheets
  • Google doc
  • Google calendar

What “good” software looks like

Before getting into the actual evaluation of your software, it’s important to remember that “good” software is subjective. 

You may pay more for a tool that on paper looks like a high expense. But that software could be super user friendly, you could use it every day, and you could save time with its features. Therefore, the “higher expense” actually ends up saving you money and time down the line. In fact, the right software can actually save you money in the long run.

Just keep this in mind as you’re doing your evaluations. 

Bonus tip: Be brutally honest with yourself in your evaluation

It’s completely normal for tools to lose their shine. A software that worked for you for years may not be a good fit for your business any more. Maybe it doesn’t help you work towards your goals, or they don’t have support anymore and you get frustrated using it. 

Try to be as honest as possible when going through your software evaluation. It’s 100% okay if you realize you need new tools. It’s also totally fine if you realize you don’t!

Evaluating your current software: A Guide

When you think about the software you're using, it can be challenging to answer the question: “does it work for your business?” But it’s true: just because something used to be the best tool for you doesn’t mean it still does.

Here’s a step-by-step guide for how you can determine if your current software — or tech stack — still works for you. 

Step 1: Identify your business needs

First things first: you need to have a clear idea of what you need your software to do, and what the day to day requirements are for your software. This first step will be the benchmark in which you’ll evaluate your current and potential software options. 

We have a section for this in our evaluation sheet to help you get this down, too. 

List current business processes

Document all your business processes such as job scheduling, customer relationship management (CRM), accounting, inventory management, and reporting.

Define your goals

Specify what you need your software to achieve. Consider factors like efficiency, scalability, user-friendliness, and integration with other tools.

Prioritize features 

Rank the importance of features your business requires now and anticipates needing in the future.

Step 2: Assess current software performance

Next, you need to look at your current software. 


Check if the software covers all essential business processes. Evaluate if it offers all the necessary features and tools. 


Assess how user-friendly the software is and if you genuinely like using it. Gather feedback from your team on their experience using it.


Determine if the software can handle increased workload as your business grows. Check if there are higher-tier plans or add-ons available.


Ensure the software integrates smoothly with other tools and systems you use.

Look for API support or built-in integrations with common business tools.

Step 3: Gather feedback from stakeholders

Next, take time to see how your software impacts others who are affected by it. 

Survey your team

Ask your employees for their input on the software’s strengths and weaknesses. Focus on areas like ease of use, functionality, and efficiency.

Talk to homeowners

Does your software actively add to your customer experience? Does it take away from it?

Step 4: Compare with alternatives

Once you’ve looked at your current software, it’s time to explore what else is out there. 

Research other options

Investigate other software solutions available in the market. Speak to your network and see what they’re using. Look for products tailored to the roofing industry or general business management tools.

Compare those to your business needs

Evaluating potential software against your business needs can highlight any gaps or holes that could be filled by new software. 

Read reviews and case studies

 Look for reviews and case studies from businesses similar to yours to gauge real-world performance and satisfaction levels.  

If you’re really interested in a specific software, you can even ask their sales team for 2-3 customers that you could speak to about their experience. 

Step 5: Conduct a cost-benefit analysis

This is where you need to get crafty, because cost doesn’t always just mean money. 

Evaluate monetary costs

Consider the total cost of ownership for your current software, including licensing fees, maintenance costs, and any hidden expenses.

Benefit assessment

Weigh the benefits your current software provides against the cost. Think about time saved, ease of use, how it impacts your business performance,error reduction, and any other quantifiable benefits.

ROI calculation

Calculate the return on investment (ROI) to determine if the software is delivering sufficient value for the money spent.

Step 6: Make an informed decision

Now that you have all the information, it’s time to look at everything and make a decision: Is your software still working for you or not?

Our template can help make this super clear. 

Step 7: Monitor and review regularly

Once you’ve conducted your review, its important that you keep it up to date. We recommend scheduling regular reviews of your software’s performance and alignment with business goals. Every year is a good cadence to review software. 

Stay updated

Keep abreast of updates and new features from your software provider.

Continuous Improvement: Always be on the lookout for new tools or improvements that can enhance your business operations

FREE TEMPLATE: Software evaluation for small businesses

Access our FREE Google Sheets template that will make it easy to review your current software — and any potential new ones.
Get it HERE.

Other business resources

A guide to upgrades and add-ons

How being smart with software can save you money

What to look for in payment processing software

An overview of roofing tech

If you want to learn more about Roofr, reach out to our team!

Join Roofr, get a free roof measurement report
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