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How to choose the best software for your business

By Nic Perry, last updated March 30, 2021

I constantly hear business owners asking what the best software in an area is, like "What's the best CRM?", "What's the best payment processor?", or "What's the best Legal Software?" The probelem with all these questions is there are dozens, sometimes hundreds of options. A few of them genuinely suck, but there are usually a number of options that could work, and exactly which one is best for you depends on exactly what your business needs, and there usually isn't an easy answer. This article will help you understand what you need to take into consideration. Later there will be articles covering specific areas, but the evaluation process is similar for all of them.

Determine your need and wish list

The first step is knowing what you are hoping for in a software. In this, there are two separate lists:

The needs list should have everything that's a deal-breaker. These vary by business and software, but might be integrations with other tools you use, exact methods of notifications, or exact features you need for your workflows. The needs list could even be your budget, sometimes no matter how great an expensive software is, it might not be worth it for your company right now.

The wants list is all the other things that would be nice, which could include things that would be deal-breakers for another business, as well as things your business would like to add to its workflow, like tasks, additional integrations, or features like templates and automation.

Evaluating Software Options

Once you have your lists, it's time to look at your options. You are looking to evaluate based on your lists, as well as the company behind the software. In the first pass, don't spend time getting it perfect, the idea is to narrow your field from the possibly hundreds of options down to 3-10.

Using your lists is the easy part, but make sure essential features look like they work the way you need. For instance, sometimes email automation means they send automatically while other times it just means templates that speed up sending emails manually. For different purposes, either of these could be exactly what you want, while the other could be totally useless for your use. At this stage you don't need to know it's perfect, but you at least need to know if it looks about right.

Evaluating the company can take more time, so while it can be part of the first pass, it should at least be after you take a quick look at features. Software might look great but have horrible customer service or be a brand new small company without much guarantee they will still exist next year. Or the software might do everything you need but doesn't seem to have been updated anytime lately and looks like it belongs on a computer from 20 years ago. I like to look in general web searches, but also specifically looking at them on and Captera which together tend to give a really well-rounded picture of a company. Statistically, 3 star reviews tend to be the most balanced, but I also like to hear the absolute worst and the absolute best (the reviews giving high ratings also often compare to previous software and why they left it)

Final Evaluation

Now that you have your short list, it's time to take a harder look at the features and the company.

Feature check: Go back to the feature lists and look at exactly how the features work, this is the time for demos, trials, and trying to see how it would look to be used at your company. You still don't need it to be perfect, but for instance, some companies will say they "integrate with your calendar" when that integration is actually only one-way. Or they have texting, but all the messages dump into a central mailbox and you need them split out by customer. Take a hard look at all your needed features and a decent look at the wants.

Company review: Now it's time to go back to the company, look for good and bad reviews, who owns the company, how old it is, where your data is stored, if it's secure, how you can get your data out if you need to, and try to get a feel for how trustworthy the company is.

Once you have made it through all that, you will hopefully see clearly the best choice. If you don't, narrow it down to 2 and use a trial or further demos to look even harder at which one you want. At a certain point, you might have to just go with your gut and jump - sometimes there is more than one great software you could go with When in doubt, I usually go with the less expensive option at this point, if they are that equal, you might as well save some money.

The Easier Way

Want to know you did all this as well as you possibly could have and made the best decision you could with the information you had?

Hire us to work with you in your search. We can help you every step of the way, from making sure your list has everything it should, to vetting your options, to picking the software most likely to help your company go to the next level.

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