Chapter 1: The Reluctance Towards Technology

It’s astonishing to observe the lack of enthusiasm surrounding technology in small businesses.

I recently worked with a contractor who expressed a strong aversion to text messaging, which truly took me by surprise. It’s perplexing; phone calls tend to be far more disruptive and time-consuming. If calls go to voicemail, you end up spending even more time retrieving and responding to them, not to mention tracking down missed connections.

An overflowing voicemail box can irritate customers, whereas text or email provides a more efficient way to manage communication. You can quickly scan messages and prioritize responses, addressing urgent matters immediately and postponing others for a later time.

In my view, it’s hard to comprehend why any small business owner, particularly those running solo operations, would shy away from text messaging.

While texts have their pros and cons compared to email, I advised my clients to use email for longer explanations while following up with a text or voicemail to highlight their needs. For anything that seemed urgent, I would at least send a text to inform them of when I could call back. This approach is simply good customer service, yet it seems many solo entrepreneurs overlook it.

Of course, some clients preferred to call regardless. Tech aversion was more common in earlier years when many didn’t have text-capable phones, or were stuck with exorbitant text messaging fees. I made it a habit to regularly check and clear my voicemail. Losing a customer due to a full voicemail box is simply foolish.

Initially, I considered offering my regular customers their own login on my website for submitting service requests. However, I was ahead of my time; few utilized that option back then. Nowadays, customers are much more accustomed to such systems, which can be more efficient than email or text. Including a voice message feature would create an ideal solution. If I were younger and still in business, I would definitely implement that.

Chapter 2: The Importance of Timely Billing

One of my guiding principles was to "Bill early, bill often." Clients remember the work you performed more recently far better than what you did weeks ago. I made it a practice to send invoices before leaving a client’s premises.

Ideally, I preferred to receive payment on the spot. When I offered electronic payment options to the contractor I mentioned earlier, he insisted on receiving a check instead. It’s frustrating. Yes, accepting credit cards incurs a small cost, but I factored that into my pricing. There’s undeniable value in receiving payment immediately; waiting for checks can delay access to funds significantly—unless you can set up a direct bank transfer.

In the latter part of my career, I used QuickBooks Online to manage invoicing. This allowed me to create an invoice in just a couple of minutes, enabling clients to pay via card from any computer, including the one where I had just completed work. This streamlined process was far superior to waiting for the next billing cycle or waiting for approval from someone higher up, which could take weeks or even months in larger organizations.

This is precisely why I focused on small businesses. I often dealt directly with the owner, most of whom understood the importance of timely payments. In contrast, larger corporations were frequently delayed.

Apple is set to simplify this process even further. Currently, businesses need a credit card reader to accept payments through their phones. However, with the upcoming Tap to Pay feature, your phone will serve as a contactless card reader, making transactions seamless. Google Pay offers a similar functionality for Android users.

If I were still in operation, I would already be using the Apple beta version for this service. It’s hard to fathom why someone like my contractor wouldn’t embrace such advancements.

While it’s true that customers may more easily dispute credit card charges than stop a check payment, if you’re dealing with such clients or if your work isn’t up to par, that’s a different challenge altogether.

Good luck navigating that, I suppose?

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