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5 Tips to Help You Navigate Square Software

Dani is a writer, actress, and entrepreneur who uses Square Retail.

Congratulations on your decision to join the Square community! As an entrepreneur who uses Square Retail, I can honestly say the platform has made my business run smoothly and seamlessly.

The platform is easy to use and beginner-friendly, so you don't have to know a lot about software or technology to get it up and running. Despite this, you can run into unnecessary trouble if you don't heed a little advice before getting started.

Before diving into these tips, it's important that you know that Square has not paid me for this article in any way. I have written these tips solely to help people avoid some of the annoying issues that no one really talks about. Bruce Lee once said, "A wise man can learn more from a foolish question than a fool can learn from a wise answer."

These five tips, at first glance, may seem simple, but that is the very reason they're often overlooked. Don't discount them—they'll save you a big headache in the long run.

Tip #1: Have a Clear Way to Identify Products

This may sound like a no-brainer, but when I started with Square, I hadn't thought about how I would identify products. Don't get me wrong—I knew I had to add my products to the system in order to ring them up, but I never gave a lot of thought to what I would use to identify them. Unfortunately, this lack of thinking showed as I ran my business and cost me a lot of wasted time.

When I started, I just added titles for my products. I didn't even bother adding pictures because I didn't have an online presence in the beginning. This may be fine if you're selling ten products. However, as my simple shop expanded to include a much larger selection of products, I found that I couldn't always remember the titles I had given them.

I got lucky with the fact that you can type in a few words of the title, and Square brings up products that may match that, allowing you to choose the right one from a list. However, don't rely on this—it will quickly become inaccurate as your product catalog expands. You'll waste a lot of time hunting through all the products to figure out what to ring up.

I decided that it was time to add photos so that I would recognize the products. While the photos were a great idea, it still didn't help because I still couldn't remember all the titles I gave the products. My offerings quickly topped a few hundred products. At that time, I had only been a Square customer for about eight months, and that's all it took for my catalog to become complete chaos.

I had no choice but to do what I should have done from the beginning—set up my product catalog like it should have been from the beginning. I essentially had to re-do my entire product catalog.

I had to go through each listing, figure out what it was, update photos, and come up with new titles and descriptions. Since I couldn't close down while I did this, it took weeks to get it done. On top of that, I had to re-train my employees on the new catalog.

This is a frustration you can avoid by setting up your product catalog correctly in the first place. You should have pictures and item descriptions ready to go. Make sure you give your items an SKU number and, if possible, put in barcode numbers. In fact, Square has a feature that can automatically generate SKU numbers for you.

Most importantly, fill out as much information as you can about your products. You never know which criteria you'll need to use to find it in the register.

Tip #2: Square Offers Different Features on Different Devices

One day, I was in a car, and I saw that a customer had sent me a message through my Square website. This was in the beginning stages of my business, and I was so excited to get a message from a potential new customer.

I eagerly tapped on my app (I had a phone holder right in front of me, so I didn't have to take my eyes off the road) and went to the message. It was about an estimate that I'd sent to her. Well, I eagerly tapped the menu button only to find out that I couldn't access estimates from the Square app for Android (I'm not sure about the app for iPhone, but I believe it's the same).

This means I had to pull over because I was going to have to log in to the Square website from my phone browser. I logged in, only to find out that I could access the estimates from the phone browser but not the messages. Imagine my frustration. I had to sit on the side of the road and flip through screens just to accomplish a small task.

No, it wasn't the end of the world. However, I expect modern business software to be a bit more efficient than that. I can say from experience that all of Square's features show up on iPads that are used for the Square Register system. This is the best way to use the square platform. However, using the Square website on a computer or mobile device doesn't give you all the features. The computer comes close, but it lacks many shortcuts that could make certain processes easier.

Square has been working on adding more features to different devices, but as of right now, the only device that has full functionality is the iPad. Hopefully they'll correct this in the future, but until then, you'll likely have to bounce back and forth between devices.

Tip #3: Swipe Instead of Type

Square gives you the option to swipe or tap your customers' credit cards or phones. However, there may be some instances where you'll need to type your customers' payment information in rather than swiping. This is perfectly okay—it's not against the rules or anything. However, it can cause a few complications that you'll probably want to avoid.

The first one, which may be commonly known by anyone who owns a business and takes cards as a form of payment, is that you'll pay higher processing fees. At first glance, it doesn't seem like too much of an increase, especially if you only type the information in occasionally. It's, at most, an additional one percent. However, if you type in payments often, that one percent really adds up. Before you know it, you'll have put a dent into your profits.

I learned this the hard way before I was using the Square register. I started my business at a local flea market, and I used the small swiper that works with mobile phones. I couldn't keep up with that tiny swiper to save my life! I must have replaced it at least five times. I found myself typing in customer payments most of the time.

After a few months, I realized that I had essentially given Square a free $200. Now, when your business is racking in six figures a year, this amount might be laughable. For a flea market vendor, $200 can be the difference between success and failure. Plus, if you're processing six figures worth of payments, you'll give them way more than $200.

The second issue, which is highly annoying, is that when you type in a customer's payment method, depending on how large the sale is, Square will hold your money for 24-48 hours. I don't know why—I'm assuming it's a safety measure—but this was a big issue for me in the beginning of my business.

My business involves customized products, and my motto is delivering the product fast and on time. In the beginning, I would use the customer's deposit to order supplies. Since I was a small-time vendor, I didn't have a lot of extra money to get the supplies on my own. This meant that when Square held up my money, I was late on ordering supplies which, in turn, meant that I was sometimes late on delivering the finished goods to my customers.

If you have disposable income or you can afford to wait on the hold to be dismissed, this may not be a big issue for you. However, if your business relies on fast deposits, save yourself a headache by swiping, not typing.

Tip #4: Square Can't Change Your EIN for Payroll Once You've Started Your Account

I'll admit, I was a bit green when I started my flea market business. I won't go into details here (that would take a whole other article), but I'll just say that I ran into some issues that caused me to have to relaunch my brand under a new name and EIN. It wasn't a big deal. Luckily it happened in the beginning before many people knew about me or my business anyway.

Square has a place on the website where you can change your EIN. It's in the Tax Forms tab under Business. Simply type in the new EIN and hit save. Seems simple enough, right? Unfortunately, I learned the hard way that it's far from simple.

I did this change and continued doing business for an entire quarter before all hell broke loose. Square files payroll forms for you automatically—this is great for busy business owners. What's not great is that no one told me that changing the EIN on the tab in Tax Forms only changed it for sales and nothing else. There is no message anywhere on the page to let you know this.

You can imagine what happened—Square filed my payroll forms under the old EIN. I didn't find out until about two weeks later when someone from the Department of Revenue reached out to me, requesting that I file my payroll information for the quarter. I won't go into detail about that here. I'll just say that the agent from the DOR was amazing and helped me straighten everything out. However, Square wasn't so forthcoming.

After contacting Square about the issue, they had someone named Mr. Childes call me (they won't connect you directly to payroll, you have to wait on a call). Mr. Childes was very professional and pleasant as he politely let me know that the Square payroll department couldn't change my EIN. All they could do was close my payroll account and open another one.

Sounds like a simple solution, right? Wrong again, my friend.

I had one of two choices. I could close only the payroll portion of my Square account and open another one, but this new one would not be linked to my current Square sales account nor any of the other services I had with Square. That meant that my employees' commissions and bonuses would have to be manually input into the new payroll account every week because their sales would not be syncing up with payroll.

The second option was to close my entire Square account and open an entirely new account. Mr. Childes even offered to import all of my settings and products from my old Square account to the new one so I wouldn't have to set it all up again (they can do all that, but they can't change a simple number). This sounds like a winner, right? For me, it was not.

Square has a loan program for businesses that have gained Square's trust. It takes a while for Square to consider your business for a loan and my business had just been recently approved. Switching to a new account would mean that I'd have to start all over from scratch, building that trust again. Plus, I had an open loan with Square in the old account, and I didn't want to jeopardize my standings with Square. So, switching the entire account was not a viable option for me.

For a while, I tried the first option, the split account. This became quite tedious after a while but Square had no solution for me. In fact, this issue (plus the next one you're going to read) is why I am no longer a Square customer, unfortunately. I solved my problem by switching to another company altogether.

Ironically, this also jeopardizes the relationship I built with Square Loans, but my business simply outgrew what Square could offer. I needed better customer service. If you keep reading, I'll dive more into this in tip number five.

Tip #5: All of Square's Departments Work Independently of Each Other

The situation with the EIN and payroll issue occurred because Square's departments don't talk to each other. It's crazy, but if you change something in one department, it doesn't change across the whole platform. You must change it in every department yourself—sales, payroll, marketing, etc.

Call me crazy, but this just seems tedious and unnecessary. As a busy business owner, you probably don't have time to contact every single one of their departments about some change you want to make to your account. Well, with Square, you'll have to make time.

It's bizarre that Square doesn't have a way to centralize information over all departments. They are supposed to be this new, innovative payment processing company, but this lack of communication is indicative of a company that doesn't have the proper infrastructure (for lack of a better term) to handle business payment processing. In the end, this can spell out big trouble for any business.

Square Is a Solid but Flawed Payment Solution for Small Businesses

I want to make it clear that I don't think Square is a bad choice for small business owners. In fact, I like most of their features and I think they make it easy for people to begin processing payments. Overall, I would recommend Square to anyone looking for a simple payment solution.

However, there are some inherent flaws that make the system inconvenient in many cases. The five tips above point out five of these flaws. The good news is that Square is consistently working on updating its platform. The company hasn't been around very long compared to other payment processors; this makes Square a baby. They've got some catching up to do and hopefully they'll get there sooner rather than later.

Many of the issues I had above came from me not reading the user's manual fully before diving into the platform. The platform makes things so easy that you'll feel you don't need to go over those fine details. However, you absolutely need to. Knowing what you can do and can't do can save you some aches and pains down the road. Start with the five tips above, then do some of your own research. Before you know it, you'll be prepared to dive into Square successfully.

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2022 Dani Alicia