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10 Small Business Software Purchasing Tips

If you’ve ever had to purchase software, you know how hard it is (and we can’t argue!) But that doesn’t always have to be the case. 

Is your business considering new software? Keep these 10 tips in mind to make the process smoother and more successful. 


1. Timeline, Timeline, Timeline

One of the most crucial things to consider is timing. When does your software have to go live? Start there and work backwards to plan your timeline for a search process, negotiations, testing, and implementation.

I once worked for a company that made a quick decision requiring a software implementation within four months. Converting a 20-store chain to a new system in that timeline was a near disaster. The accounting team didn’t get their forms set up correctly, and there were issues that hadn’t been tested.

You can avoid this by planning ahead. Give yourself multiple months of cushion.


2. Training

One of the most crucial things to consider is timing. When does your software have to go live? Start there and work backwards to plan your timeline for a search process, negotiations, te

3. In-Person Time is Key

One of the most crucial things to consider is timing. When does your software have to go live? Start there and work backwards to plan your timeline for a search process, negotiations, te


4. Get an Apples to Apples Comparison

When I was purchasing POS software, I found it very frustrating that all of the quotes used different terminology, price structures, contract lengths, and support fees.

So I created a spreadsheet to translate each category into a comparable number. Eventually, I was able to get to an apples to apples comparison. I highly recommend doing this, otherwise it will be impossible to know what your true cost will be.

5. Consider using secondhand hardware

Many software companies will try to sell you printers, scanners, and more with their software. Do a bit of research to make sure you aren’t paying too much. There are providers that sell refurbished hardware at much lower costs.

6. The more references, the better

Software companies often provide a list of references, but only of companies that like their software! Do some research and try to find someone else using the software. Many online forums provide insight and reviews.

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7. Think Strategically

It is important to consider where you’d like to be in three, five, even fifteen years when implementing new software. Many business don’t factor in their growth plans and outgrow software too quickly.

8. Trust your instincts

I’ve been in a room with a team while they viewed a new POS system they thought was not intuitive. It was an eyesore, and creating a sale and tracking rewards was confusing – but they were short on time and needed a low-cost solution. Think it panned out? Remember: Always trust your instincts.

9. All contracts are negotiable

Make sure you read through the contract thoroughly. There are often hidden fees or surprise charges. If you don’t understand each line, ask. And don’t forget to negotiate! Ask for a free license or a longer support window.

10. Don’t forget integration

You may have other software programs used in daily operations. It is critical that any new software can integrate with your current setup, unless you are replacing it.

For example, do you have an accounting system already but want to add a POS? Then your new POS must integrate with your accounting system or you will be doing double work.  


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