What Not to Do With AI: The Mistakes That Turn a Powerful Tool Into a Distraction
There’s no shortage of content about what AI can do. The use cases, the workflows, the prompts, the platforms — the enthusiasm is real and much of it is warranted. But at the April 2026 DIG Philly meeting, TJ Hock of Rentwell took a few minutes to go the other direction: here’s what doesn’t work, what he’s learned the hard way, and the traps that catch even well-intentioned adopters.
It’s some of the most practical advice in the entire session.
Prompting Without Context
This one came up repeatedly throughout the meeting, but TJ named it explicitly as a common mistake. Asking AI a vague question and expecting a useful answer is like handing a new employee an incomplete brief and being disappointed when the work misses the mark. The quality of the output is inseparable from the quality of the input. If you’re not getting useful answers, the first place to look is the question you’re asking.
Trusting the Output Blindly
AI is confident. It doesn’t hedge the way a cautious person might, and it doesn’t always flag when it’s working from incomplete or outdated information — as the tax table example from earlier in the meeting illustrated. You have to stay in the loop. Proofread. Cross-reference when the stakes are high. Your judgment doesn’t get outsourced just because AI produced an answer.
Trying 20 Tools at Once
This might be the most common mistake among people who are genuinely excited about AI and want to get the most out of it. There are dozens of platforms, each with different strengths, and it’s tempting to experiment with all of them simultaneously. TJ’s advice is direct: don’t. Pick one. Get comfortable with it. Then pick one area within that tool to focus on until you’ve genuinely developed some proficiency. Spreading attention across too many platforms too quickly is a reliable way to get shallow results from all of them and real results from none.
Letting AI Create More Noise
This one is subtle but important. AI is supposed to reduce the signal-to-noise problem — helping you find clarity, prioritize better, move faster on the things that matter. But if you’re not intentional about how you use it, it can do the opposite. Another tool to check. Another output to process. Another layer of complexity added to an already complex day. If AI is creating more distraction than it’s eliminating, something has gone wrong in how it’s being used.
Using AI to Avoid Hard Decisions
Perhaps the most honest item on TJ’s list. There’s a version of AI use that looks productive but is actually a form of avoidance — running one more analysis, generating one more framework, asking one more question, when what the situation actually calls for is a decision. AI is genuinely useful for thinking through complexity. It is not a substitute for judgment, and it should never become a reason to delay the call you already know you need to make.
TJ put it plainly: sometimes just picking up the phone is the easiest thing to do. Not everything needs to be analyzed. Not every decision benefits from another layer of AI input. Knowing when to use the tool — and when to just act — is part of using it well.
The Common Thread
What connects all of these mistakes is a version of the same error: treating AI as something that happens to your workflow rather than something you actively direct. Prompting without context, trusting blindly, jumping between tools, adding noise, avoiding decisions — each of these reflects a passive relationship with a tool that rewards intentionality.
The people getting the most out of AI aren’t the ones using it the most. They’re the ones using it most deliberately: one platform, one use case at a time, with clear prompts, healthy skepticism, and the judgment to know when the right answer is to close the laptop and make the call.
Rob Coldwell and TJ Hock are the owners of Rentwell Property Management. They were the featured speakers at the April meeting of DIG Philly in King of Prussia. Hear their full presentation and many more on our podcast “Living Well with Rentwell”.
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For more information on property management in the Northern Liberties area, schedule a free owners’ consultation at Rentwell.com


