10 Software Selection Considerations for Small Businesses

As a small business owner, choosing what software to run your business with can be a daunting task. This is especially true for many business owners who may not be technology savvy. Most small businesses will have smaller technology budgets compared to their enterprise counterparts. Selecting the wrong software can even harm your organization. Causing disaster when spending should go towards growing the organization in other areas.

Here are ten concepts to keep in mind when selecting any type of software for your business:

  1. Define your Desired Benefits
  2. Determine What you Need
  3. Research Your Options
  4. Cheap May Not Mean Inexpensive
  5. Configuration vs.Customization
  6. The Perfect Solutions Does Not Exist
  7. Integrate When Possible
  8. Get Stakeholder Buy-in
  9. Document Processes & Procedures
  10. When in Doubt, Hire an Expert

1: Define your Desired Benefits

Return on Investment

Leading a small business means things move quickly and it may seem like a luxury to be able to step back and take a deep dive into your business. Not understanding your expectations complicates determining the best fit for your business. In some cases, this causes difficulty in determining if you even required software to solve the problem.

  1. What are the business benefits you are trying to achieve? Efficiency? Productivity? Higher revenue? Reduced headcount?
  2. What will success look like?
  3. How will you measure the Return on Investment (ROI)?
  4. What are the top 5 pain points and/or problems you are trying to solve?

If you can answer these questions, you will make the rest of your selection process much simpler.

2: Determine What You Need

Once you’ve decided on your desired benefits of having the software, you will need to answer a few additional questions to help you create your initial feature shortlist.

For example:

  1. How many users/employees will need access to the system?
  2. Do your employees always operate in the office? Are they on the road a lot? At project sites? Onsite meetings with customers?
  3. How accessible do you need the software?
  4. Can the software be easily accessed by everyone who needs it, or is it restricted to just a select few users?
  5. Should it only be accessed from certain locations and/or devices, or should it allow for remote connectivity?
  6. Should users be able to access the software on mobile devices? On tablets?
  7. Do you need the software available in multiple languages for various groups of users?
  8. Do you have users with special needs such as visually impaired, colour blindness that require unfettered access?
  9. Accessibility is a big deal when you are investing in expensive software that will ideally be around for several years.
  10. Do you want to build a remote-first organization?
  11. Many modern companies are adopting a work from home (WFH) culture which has very different software needs than a traditional brick and mortar company.
  12. Do you require users to be able to collaborate?
  13. How much collaboration a platform supports collaboration is very important.
  14. In many situations, you will need the platform to facilitate communication between different teams, support staff, and even customers.
  15. Do you need any new software to communicate with existing platforms?
  16. Does either of the systems have the ability to integrate?
  17. How much growth do you expect in both the company and the user count?
  18. How important is the level of support you receive?
  19. What kind of implementation support will you require?
  20. What kind of ongoing support will you require?
  21. Do you have onsite IT support?
  22. Will you require vendor support?
  23. Are there specific features that are critical to achieving the desired business benefits?
  24. What is your budget for implementation services, ongoing support, and licensing?
  25. Where do you see the business 5-10 years from now?
  26. What needs can you anticipate at that time to accomplish those goals?
  27. How much growth in users, customers, sales, inventory, etc. will you need the system to accommodate?

These are just some of the questions you will need to answer before you create your initial product shortlist.

3: Research Your Options

Trust me when I say that doing research upfront will save you lots of time and money. Not only in picking your final solution, but in preventing the costly mistake of switching solutions in the future. Picking the wrong platform can be a very hard pill to swallow and will most likely set your company back.

Identify options in the market and make a shortlist. I like to create a spreadsheet with the software options and all the key features I desire. Then I’ll rate each system on a scale of 1-10 for each of the following to help me rank the options:

  • Desired benefits
  • Desired features
  • Ease of use
  • Security
  • Product and user reviews
  • Pricing

When it comes to choosing software, there is always the debate on pricing versus value. Should you spend extra money to get a particular feature? Or, is it better to reduce spending and forego the additional features and discover an alternative way to handle a certain task? There are no clear-cut rules to follow here, but there is some prudent advice. Utilize the 80/20 rule, also known as the Pareto Principle which asserts that “80% of outcomes (or outputs) result from 20% of all causes (or inputs) for any given event.” When researching business software, we can utilize this rule is to identify features that are potentially the most productive and the most profitable and then make them a priority.

When it comes to purchasing software this can be applied by looking at features that cover 80% of your outcomes. For example, if most of the time your customers pay via Mastercard but very rarely pay by American Express, you would want to make sure the platform supported Mastercard. You would do so by prioritizing platforms that supported Mastercard and would not penalize platforms that did not support Amex. Essentially, you would not want to pay extra or sacrifice features to gain the support of Amex, because the majority of your sales are via Mastercard.

Next, speak with your industry colleagues and see what other companies are utilizing. This can be helpful in not only learning about what platforms are out there but also finding out firsthand what is working and more importantly what is not working.

Next, utilize free trials and get demos from vendors when possible. There is nothing better than getting your hands on a platform to see what you can do with it. That being said, do not get distracted by shiny objects. Focus on your core features and how you can utilize them in the systems. Any features outside of that are icing on the cake. Like most business owners, you have limited time, so evaluate from an objective perspective and limit the time you take to “explore” nice-to-haves.

Next, should you rely on reviews and ratings? Well, yes and no. The goal is to identify the software and platforms that result in the desired benefits and outcomes that you have already defined. Once you narrow down your choices to the platforms that accomplish this, then you should study the reviews and ratings that are available. These are good indicators of overall satisfaction for a product, but take these with a grain of salt. Why you may ask? People are more likely to provide a negative review. In addition, watch out for fake reviews which can be spotted with the following tell-tale signs:

  1. There are no details from the reviewer’s profile or the reviewer has inconsistent reviewing methods. This could indicate computerized spam reviews.
  2. The review includes links to third-party websites and/or products in an attempt to draw customers away from the product you are interested in.
  3. The review content is repeated verbatim as new reviewers (persons).
  4. The review sounds too good. Many times individuals are paid to leave good reviews to make a product look better than it is. Much in the same way that competitors will pay individuals to leave negative reviews to prompt their products.

Lastly, do not settle for the first platform you find. Commit to doing the research, read the reviews, and solicit recommendations from colleagues and experts to make sure you are picking the best tool for your business.

4: Cheap May Not Mean Inexpensive

Most companies cite cost as the primary factor when choosing new software for their business. There are many cheap or free options available on the market for almost any software need. This includes platforms that offer a Free subscription option before making you commit to a paid subscription and even Open Source software that offer the software itself at no cost.

You really should not pick a platform solely because it is a “cheap” option. The following are just some of the reasons why this can be a very costly mistake:

  1. Switching from a platform after you decide that it does not fit your business needs can be extremely costly in both money and time.
  2. Free solutions often use other means for generating revenue such as advertising and feature limitations which can be a hindrance, especially for customer-facing features.
  3. Open Source software never comes with technical support, implementation services, nor ongoing maintenance.
  4. Free solutions often only have limited support options such as Forums or if you are lucky email support.
  5. Do not forget to consider implementation costs and ongoing maintenance costs that are not typically covered in monthly licenses.

Remember, software platforms can be expensive if evaluated as a cost on their own; however, if you look at it from a Return on Investment (ROI) perspective, it will pay for itself over time.

5: Configuration vs. Customization

While these two terms sound very similar, they have very different costs associated with them when it comes to software platform implementations.

When it comes to configuring a platform we are talking about using the existing features within the platform to set it up to operate as you desire for your business. An example of this would be uploading a company logo to display within the software. Other examples would be to set up categories for inventory items, configuring tax rules, or setting up approval workflows. These are items that do not require assistance from the vendor to set up and allow you to leverage all of the existing functionality within the platform.

Customization on the other hand typically refers to having custom code written to interact with the platform. Some platforms have a built-in scripting engine and others have Application Programming Interfaces (APIs) that allow custom code to be used with the system. This type of work is used to extend the functionality of a platform beyond what is offered by default. Many platforms will charge extra licensing fees for the ability to do this. In all cases, you will either need to hire the vendor or hire a third-party developer to do the work. This level of customization comes with risks depending on the platform. If the platform releases new versions which are not backwards compatible, you may be required to update your customization and pay for them all over again.

Now, why would you choose to customize over configure if there is higher cost and risk? Well if the feature you are missing is a priority to accomplishing the goals you started with, it may be worth the risk if maintained regularly. Additionally, if no other platform you have evaluated offers this functionality it may be your only option for accomplishing that particular goal. The key here is to ensure you put aside a healthy budget for implementing and maintaining these types of customizations.

6: The Perfect Solution Does Not Exist

As with anything, if you have enough money anything is possible; however, unless you are willing to spend millions of dollars on and have many years to commit to a completely custom-developed solution, attaining the “perfect solution” is not possible.

This comes back to the 80/20 rule. Solve the 20% of tasks that provide 80% of your output. Do not worry about programmatically handling all of your one-off scenarios and processes. The amount of time and money you will spend on handling one-off scenarios will remove all return on investment you could have realized from the software.

In addition, expect to change how you are currently doing things. At some point when you are evaluating software you will hear the phrase “it is the way we have always done it”. These are the areas that I recommend digging into sooner than later. Understanding the “why” in these situations will reveal some interesting things. Everything from “the current system made us do it this way” to “I do not know, we just do it that way” will be revealed. These are typically areas that have the most to gain from new processes and efficiencies in new software systems.

When evaluating software, do not always assume you doing everything the best way possible today. Sometimes the software can teach you industry best practices that you were not aware of and by a

7: Integrate When Possible

I am all about maximizing the value of your investment. After all, you are spending money to make your company more successful, right? There is no better way to get more value out of new software than to ensure that it works with the other software that runs your business. Now, I am not proposing that every piece of software needs to communicate with each other, but rather when you identify areas that require administrative overhead, such as double-entry of data, you should evaluate the possibility of integration.

For example, you may want to have your CRM system communicate with your marketing software so that you can automatically push lead and customer information and target those groups. You may want to have your point of sale system automatically push sales transaction data into your accounting system. Or you may want to have your web store push online sales orders into your inventory system to facilitate fulfillment. The combinations are limitless, assuming you are picking solutions that are forward-thinking and offer the ability to integrate with other systems.

Integrations can help connect your new software to everything else your team is using. Allowing your business to get more done faster.

8: Get Stakeholder Buy-In

If your team will not use the software, there is no point in implementing it. Adoption is crucial to the success of your implementation. This comes down to you needing “buy-in” from key stakeholders in the company to ensure they see the value of using the new system. Include anyone who will be affected by the software change in presentations and discussions. That could include:

  • Department employees
  • Managers in charge of the software budget
  • Executives who need to approve the purchase of
  • IT personnel who will implement the new software
  • Management who will be responsible for driving the change

If they feel you are making the change just to have new software, adoption will be very difficult. If they feel that using the new software benefits them somehow, they will want to use it and, in fact, be begging you for it. This means finding the “reason” for each department to want to use the new system. It may be that entering sales orders will take a fraction of the time, or that you are reducing data double-entry significantly, or that you are automating current manual processes. The key will be to find the 2-3 takeaways that will excite each group within your organization to want to make the effort to learn the new software and utilize it as you desire.

Do not just find a new software system; make sure everyone on your team wants to use it.

9:Document Processes & Procedures

This, in my opinion, is one of the most crucial steps that nearly all software implementations lack. All of your employees will be using this new software, but can you guarantee that everyone will be using it in the same way? Everyone needs to be on the same page to prevent issues down the road. Ever hear the saying “garbage in, garbage out”? It is referring to when users do not use the software correctly and the input into the system is not what is desired. If all your data going in is flawed from the start, then you will never realize the full potential of what you were wanting as the original benefit for implementing the software in the first place.

So how do you keep everyone on the same page and working toward the goals you set out? Communication, documentation, and expectations. These three items will help to ensure that your team is leveraging your investment properly.


Communicate about everything regarding this new software. Start talking about it early in the process. Get feedback from your team early and often regarding what they think their needs are and how they rate the importance of features. Communicate “why” you chose the system that you picked, what problems it solves, what are the benefits to the company and the team. Also, be mindful of the technologies you use to communicate. Information you want to be retained and referred to often should not be communicated in systems like chat and email, but rather using documentation systems, wikis, and help systems. Quick information relating to a point in time is best communicated using chat and email systems.


Creating user software manuals and process manuals will help to ensure that all users understand how you expect them to utilize the software. Complicated procedures should be broken down into bite-sized steps and include images and screenshots for reference. Use numbered bullet lists to make consumption of long instructions easier. Outline the process that you want to follow 80% of the time and list the known exceptions to the rule and how you want them dealt with. Get feedback from users on whether the documentation is easy to understand and if not refine and rework it. Lastly, don’t provide printed manuals. Instead, provide them in a format that is digital, easy to search, and quick to access. Printed manuals get outdated quickly, are hard to find information in, and get shoved on a shelf somewhere only to be forgotten.


Set clear expectations, that users are to follow guidelines that you have laid out. Let them know that with new software there will be challenges in the beginning and that is expected. Tell them that challenges do not mean it is not working, but that you need to learn from them and pivot processes as required. No one likes change, especially when it comes to “the way we have always done things”. Expect pushback from some users, but make it clear that by learning the new system, they will be able to do their job more efficiently and be more productive.

In the end, make sure your employees not only understand how to use the new software, but what they should be using it for too.

10: When in Doubt, Ask an Expert

Sometimes you are too busy running your business and you do not have the time to invest in the selection process. Sometimes you are not comfortable enough with the technology to make the decision. In these cases, it might make sense to hire an expert to assist in the process.

The following are some things to consider when selecting a consultant to assist you in the process:

  • Software vendors are there to sell their software to you and do not approach consulting objectively. Their goal is to get you to buy their product.
  • Software Consulting firms that specialize in the deployment of one or two platforms can be a little more objective than software vendors; however, their goal is to sell you implementation services.
  • Managed Service Providers typically will have experience using many different platforms from their various customers; however, they are not necessarily experts in all of them. As a result, they may not be willing to provide recommendations for certain types of software.
  • Technology consulting firms can provide a 3rd party perspective on platforms and technologies without having a vested interest in the actual sales of any one particular platform. That being said, ensure the firm you are working with is taking a bipartisan approach to their consulting.

Selecting new software for your small business can be a very daunting and time-consuming process. If you are not prepared for that, it may mean your project never takes off in the first place. To be successful ensure you have the willingness to commit and follow through both financially and time-wise.

If you feel you cannot execute a project such as this on your own, you may want to check out our services at Technodus Consulting and see how we can assist you in successfully implementing new software for your business.

Hi, I’m chad

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