When Automations & Systems Don't Work

November 15, 2025

The purpose of automations and systems is to reduce friction and make tasks easier. The idea is to reduce the work required to perform a task. If you can take a task normally performed by humans and either create a system to standardize how the task is performed or automate the task, your business should be more efficient and more productive, right?

But…
​and this is a big but, the system or automation has to actually work as intended. When it doesn’t, it just creates more work requiring problem solving, manual workarounds, and, wait for it... it requires a person to think for themselves. This morning I personally experienced a system/automation failure when rescheduling a room booking at one of the large hotel chains. I don’t want to name the chain but its initials are Marriott. Oops!

This is what happened and why if you’re using automations and systems in your business (and you should be), you should do some thorough testing and play the “what if” game. A programmer would call it an “If/Then” statement. If this happens, then do this. I had booked a room for two days using my reward points. The need came up for me to reschedule the booking. The woman at the hotel handled the transaction and assured me my points would be refunded and I could use them for the new booking. But they were not refunded. Turns out she was supposed to release the points at the time she cancelled the old booking. Then I was supposed to rebook the room online. But my points were not there.

A Person Fixed It

Here’s where the failure happened. They definitely have a system in place. They have automations in place. However, the release of the points was left out of the automation. The woman at the hotel thought it was automatic. The resolution required a call to the corporate level. A simple inclusion of the reward point refund would have avoided calling the corporate booking office and having a human try to figure out how to fix it. And by the way she did fix it and as usual was very courteous and accommodating as has always been my experience in dealing with the Marriott corporate office.

All this is to say that I love systems and automations. They can save your business and help you grow. But they have to work. They have to be tested. And you have to include a thinking human in the equation just in case there’s a failure. Remember you own your business and you run it. Your AI apps do not. They are your assistants. And they need to be monitored and adjusted from time to time.

A New Position
​Here’s a need and an opportunity. Small businesses need AI now. Those that don’t use it will be left behind. But there’s a problem. Most business owners don’t have a clue how to use it. And why should they? They’ve been more concerned with things like their dysfunctional team, their cash flow, and sales and marketing. How would they have time to learn the ins and outs of AI, automations, and systems. So when hiring for your business consider hiring someone who can be your AI Wrangler. Someone who can manage your AI apps, automations, and your systems. And yes I see the irony here in hiring a human to manage the systems put into place to replace the work of humans. But this is a position that will become increasingly necessary in the very near future. Like tomorrow. Maybe even this afternoon.

Here are some action steps:
​1. Start looking now for someone to put into an AI/Automation and systems management position.

2. Start by looking at your current employees if you have any. There might be someone that can be trained to do the job.

3. Take 30 minutes a day to learn about AI and automations yourself. The more you know the better you will be at recognizing the right people to hire for the position. You don’t have to be an expert. Just become familiar with it.

That's it for this time. See you next week!

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