How do you evaluate software for your business? (2x free worksheet bonus)

When you’re looking at a piece of software for you and your team in your business, how on earth do you know if that software is any good for you?

From CRM tools to accounting software, from WordPress plugins to productivity apps, how do you determine if a tool is the right software for your business?

What can you to do ‘test’ the software to see if it meets your needs?

Are you someone who dreads trying to find a new software tool, and relies heavily on recommendations from others? Have you been caught out trying a new piece of software, been using it for a few weeks, and then realise that it’s not going to do what you need? Or it can’t do that one thing you need it to do?

In this guide, I want to help you choose software with less hassle with two really easy-to-follow processes that are designed for switched-on business owners. These processes are pragmatic and straightforward, and include:

  1. A process to help you shortlist software you want to try.
  2. And a process to evaluate the shortlisted apps – with the view to choosing one of them as the winner

These processes are offered to you to save you lots of time. Please do adjust, change, simplify or add complexity to this process in any way that suits you (*I’d love to know how you use them… let me know).


6 crucial rules about finding the right software

It’s worth having some key thoughts in your head before you start your selection of software products. When working with business owners, it’s very common for expectations to be pretty high about what a piece of software can do (a.k.a silver bullet syndrome).

If your expectations are really high, there’s a danger of never finding a tool to help you, and therefore you’ll hold yourself back from making progress in your business.

So here are some really important rules to be mindful of:


1) If you have a long wish list of requirements, the harder it will be to find some software to ‘do it all’

Despite being really obvious, it’s amazing how often this is forgotten. It’s akin to having a list of 100 toys on your Christmas list as a child, and you’re hoping that Santa will bring you all of them! It obviously depends on your requirements, but an all-in-one piece of software that does everything for you is pretty rare.

If you do have a long list of requirements, then create a spreadsheet. Give each of those requirements a priority to help you with your research. e.g. 1 = must-have, 2 = really want, 3 = nice to have.

Which leads nicely to the next point.


2) It’s completely OK to have several software tools in your business

Again, it’s completely obvious. But under the guise of saving money, it’s still really common to see business owners trying to save costs by having one software app, where 2, 3 or even 4 tools might be best. If you want an amazing tool for creating recurring payments, you wouldn’t typically want that to be the same tool that you use for email marketing. Although tools like that do exist, there are usually compromises in at least one of those tools.

Group your requirements by types of feature. e.g. taking payments or subscriptions would be one group, sending emails and automating emails would be another group. Then look for software that solves problems per group. An email tool for email problems. A payment tool for payment challenges. etc.


3) What’s best for your friend’s business might not be best for you…

I’m sure you ask your fellow business owner friends for advice on what software tools they recommend for solving a problem. It’s a great way to get ideas for working out what software you need. There are nuances in your business that might mean the software just won’t do what you need.

(Of course, the inverse of this rule is also true… what’s best for your friend’s business is amazing for you.)

Often business owners will struggle to articulate the objective reasons why they’ve selected some software. They’ll often be gushy, saying “it’s just amazing, you’ve got to try it”… but won’t give you any real detail.

Use recommendations from your friends to feed process 1 and/or process 2 below, to help you with your research and evaluation.


4) Do you like or love the software? Or does it annoy you?

This is covered in the process later, but it’s important enough to mention here. You’ve got to enjoy using the software you choose. If the software is annoying, then you’re going to use it far less than you need to. If your staff dislike using the software, they’re not going to use it. This means the software is just a cost and doesn’t really help you.

If you don’t like the user interface, how the support team talk to you, or how it integrates with other tools, then change that software for a new tool. Life is too short to be irritated by a bit of technology



5) This isn’t a life-long commitment… it can be a stepping stone

It’s completely OK to use software for a period of weeks, months or even a couple of years to then outgrow it. A software tool that helps you move forwards towards your business goals for the next 6 months, 12 months, or more is still a wise investment. You’ll learn the limitations of the software, but become clearer on what you want too.

From developing software for clients, I see this time and time again. You’ll become so much clearer on what you need from a software tool once you choose a software tool and start using it. You’ll learn what you really need, and what’s going to really move you forwards. So much so, that choosing any tool that’s close to what you need is the fastest way to work out what your priorities really are.

That’s why thinking of your next software choice as a ‘stepping stone’ rather than a permanent change will help you.


6) You’ll probably only need 20% of what a software tool can do…

For more mature software products which are packed with features, you’ll find you only use a subset of that functionality. And that’s very normal. And this makes it easier to do your software research because what you need is a smaller list compared to what most products can do.

Try to focus on what you need, rather than get too seduced by the whizzy features a software product can offer. I know as a business owner that’s difficult to do, as most of us LOVE whizzy features…!

But that now leads us to the first process. Shortlisting…



Process 1 – Creating a shortlist of 2-4 software tools

Rather than focusing on feature lists or being excited about the ‘power’ of a software solution, this process is designed to tease out the functionality that you need right now.

  • If you’re a detail-oriented person, you’ll enjoy all 6 steps.
  • If you’re not much of a detail person, just do Steps 1 & 2, 5 & 6.


Step 1 – Create a spreadsheet

You might have guessed that this was coming! Create a spreadsheet with the following headings (sample available in the free download):

  • The specific problem I want to solve
  • How important is this problem to me? (1 = critical, 2 = important, 3 = nice to have)
  • What area or group does this fall into? (e.g. automation, accounting, customer database, dashboards, taking payments, etc).
  • Any additional notes or thoughts



Step 2 – Fill in the spreadsheet with at least 3 business problems

Fill the spreadsheet in using the column headers as a guide to create a list of business problems. There’s no right way or wrong way to do this, it’s your spreadsheet. Make it work for you. The examples in the download are there to help give you inspiration.

If you have between 3 to 7 problems to solve per group, your research should be fairly straightforward. If you have more than that, you might find research a little more difficult as you’ve got to check multiple features.


Step 3 – Sort the sheet by ‘priority’, then by ‘group’ (optional, but recommended)

This will sort your problems into groups, with the highest priority problems first. This simply makes it easier for you to do your research by combining groups. You’ll probably want to start with between 2 to 5 problems to evaluate initially. You can always add more later.


Step 4 – Create a new spreadsheet for software products

Create a spreadsheet with the following headings (a sample for this is also available in the free download):

  • Software product name
  • Billing frequency (monthly, annual, quarterly, lifetime)
  • Price for the number of users you need
  • Set up cost (if any)
  • How long is the trial period? (7 days, 14 days, 30 days, no trial)
  • Is there a refund guarantee? What is it?
  • What support is on offer? (email, telephone, chat)
  • Do they have a support / knowledgebase / documentation section?
  • How many of the listed problems does this appear to solve?
  • Should we review this tool?
  • Do I particularly like this tool?


Step 5 – Start researching software (and add it to the spreadsheet)

There are many ways to do this, including asking your business friends. You can research “best software for _____” or “software for doing _______”. Start adding to your spreadsheet. Add as much or as little detail as you need. If you’re a detail person, add plenty of information to help you decide. If you don’t like too much detail, then just use the columns that matter to you.

Feel free to use your intuition and instincts. The two columns that will help with this are “Should we review this tool?” and “Do I particularly like this tool?”. If a tool looks and feels great, then by all means test it.

Add as many tools as you like. You might want to add just 2 or 3, you might want to choose 10. Completely up to you.


Step 6 – Decide on some criteria and choose your 2-4 tools to test

Now you have your list of software, choose your decision method.

  • Are you going for the cheapest?
  • Are you going for the tool that you’re excited by?
  • Do you want the tool that has no setup cost?
  • Do you like the tool that has the best customer support?

The objective is to give yourself a small list of software tools to now test. You don’t want more than 2-4 tools because you’re reducing choices to help with your decision-making. Having fewer tools on the shortlist will save you time during the testing bit.


Helpful trick: you can always pick just 2 tools you feel are promising, and then test further tools if you want to.



Process 2 – How to evaluate each shortlisted software app to pick a winner

In short, this process is simply about trying to use the software to implement solutions for each of the problems you’ve listed (from step 1 and 2 in process 1). I’ve created some worksheets as a basis for you to print and use, or you can use them as a guide for creating your own version.


Step 1 – Flesh out each of your business problems in more detail (using a worksheet)

Using your spreadsheet of problems that you want to solve with a software product, you’re going to fill in a worksheet (Part A – Problem Summary Worksheet). The free download contains blank printable worksheets in A4, plus a filled-in example for you to refer to.

This worksheet describes:

  • What problem do I have?
  • What outcome do I want?
  • What do I want to happen?


Brainstorm enough detail here so that you know what outcome you are attempting to achieve. Fill in a worksheet for each of the problems you wish to solve with the software, as it’s going to help you to evaluate whether or not your shortlisted software product can meet your business needs.

You’ll probably want to start with between 2 to 5 problems to expand on initially. You can always test more problems later. You want to start with the highest priority problems first. Simply put, if a piece of software doesn’t solve your core business need on the first handful of problems, you can save a lot of time and dismiss it early from the shortlist.

Whilst this might seem like a lot of work, you’ll be amazed at just how much time this is going to save you in the long term. It’s going to help you to become clearer on what business processes you’re going to augment with the software. Essentially this step encourages you to think about the key steps of your processes and where the software tool fits within this.


Step 2 – Try to implement and solve every problem for every piece of software you’ve shortlisted

Using the second worksheet in the resource pack (Part B – Software Worksheet), you’re going to use each piece of software and try to implement a solution for each problem that you’ve described in Part A – Problem Summary Worksheet.

This is where you’ll want a short list of 2-4 software tools and a short list of 2-5 problems to test, otherwise, this can become a really long software evaluation process.

  • e.g. if you’ve got 8 problems listed, and you have 4 products to test, then you have 8 x 4 = 32 tests to do.
  • e.g. If you have listed 5 problems, and you have 4 products to test, then you have 5 x 4 = 20 tests to do.
  • e.g. If you’ve listed 3 problems, and you have 3 products to test, then you have 3 x 3 = 9 tests to do.

If you’re a busy business owner, then you want to be pragmatic with your time as you’ll only have limited time to evaluate all of these software tools. You can always add more problems later if you want to make sure a software tool is suited to your business needs.


The evaluation worksheet asks you the following:

  • Your notes on how to solve the problem using the piece of software
  • Is the problem solvable using the software?
  • How easy is the software to use?
  • How does the software feel?
  • How well does it do the job?


This is where you can make notes on the usability and suitability of the software. If you need any technical support, do they help you solve the problem? Does the documentation explain to implement what you need? And of course, does the software have the technical capability and tools available to do what you need?



Step 3 – Make a choice

By now you’ll have a really solid grasp of the software tools, and you’ll know which ones have the features and functionality that you’re looking for. You’ll know by this stage which software tool you like, and what tool(s) you find frustrating. Once you get started, you’ll notice how quickly this method eliminates completely unsuitable software.

These 2 processes should make your decision-making process much easier, and help you with selecting the right tools for your business.

I’ve found from my own experience that the best way to know if the software is right for you is to simply test it. So I have shared my own process with you to help you find the right one for you.


In summary…

Whilst there is plenty of detail for you in this article, the process for evaluating different software to determine its suitability for your business is actually pretty simple.

  1. Make a list of the problems you want to solve
  2. Shortlist some software you think will do the job
  3. Create detail for each problem, ready to test each software tool
  4. Test each tool with every scenario
  5. Make a choice on what has best functionality and usability

If you work in project management, IT or software engineering, you’ll appreciate that this process is essentially a simplified version of a test plan. It works, it’s efficient, and it’ll help you to choose the right type of software you’re going to need.

You’re very welcome to download the free resource, where I’ve created a pack to help you with your evaluation process. It includes all of the documents I’ve mentioned in this article, in addition to some examples to help you get going.

I’d love to know how you get on. Please feel free to drop me a line via the website contact form.

Free Download
Easy Software Evaluation for Business Owners Pack
An easy-to-use pack of spreadsheets and worksheets designed to help you evaluate software tools and ensure that they're the best possible fit for you and your business. Includes:
  • a spreadsheet to summarise your 'business problems'
  • a spreadsheet to shortlist possible software products
  • a worksheet for planning a simple test for each software tool
  • a worksheet for you to track your progress using that software tool
    Your Name(Required)
    We will collect, use and protect your data in accordance with our Privacy Policy. In short, we respect your information and never share it.