AI & ChatGPT for Small Business: Don’t Believe (All) The Hype

By: Jeff Heybruck

If you’re a small business owner, you’ve probably heard the hype: ChatGPT will revolutionize how you run your business. The truth is a bit more nuanced.

My staff and I paid $170 for a webinar on ChatGPT and stopped watching it 30 minutes in. There were no real-world examples, just ‘theoretical’ use cases that didn’t really apply to our own day-to-day. So today, I’m sharing what I’ve learned from using ChatGPT—with real use cases. And I won’t charge you a dime.

From sorting through resumes to analyzing clearing accounts, here’s my key takeaway: Chat GPT can be a little too eager to please, but it can be incredibly useful if you know when and how to use it.

Here’s a breakdown of each use case, whether or not ChatGPT was able to do the job and what I learned along the way.

Use Case #1: Resume Screening

When we first built a Custom ChatGPT to screen resumes for an open position, it worked great. We trained it by showing strong resumes alongside some complete duds, then asked it to outline the differences and learn the resume characteristics we valued most. For a while, the results were exactly what we hoped for.

But two months later, the quality of the resumes it selected dropped. To fix this, we built a second Custom GPT, but that one never performed well. Thinking we might be doing something wrong, we even tried a published GPT designed for resume review — but its results were worse. In some cases, ChatGPT highlighted resumes that were downright awful. On two separate occasions, it even gave us completely made-up email addresses for candidates. During another batch review, it fabricated commuting distances for applicants who simply listed “Charlotte, NC” as their address. Why?

By default, ChatGPT is stateless — meaning it doesn’t remember what you said in previous chats or days — unless you’re using ChatGPT’s new memory feature or maintaining a well-structured Custom GPT. Without that, ChatGPT will stop “acting trained,” and you’ll find yourself having to re-teach it again and again.

The verdict: ChatGPT can be a real time-saver for screening resumes, but to get consistent, reliable results you need to build and maintain a Custom GPT or use the new memory feature. Otherwise, you risk wasting time re-training it for every new position. (That lesson really hit home for us during the resume exercise with Lucrum — but it applies to any situation where you want ChatGPT to stay sharp over time.)

Use Case #2: Comparing Long Documents

One of our clients has a very inexpensive General Liability policy on some timberland, offered through an industry association. The old carrier was not renewing the policy and the agent (who likely received minimal commission) was not very helpful in explaining the differences between the old and new.

I had neither the time nor the desire to read between 89 and 105 pages so I asked ChatGPT if it could help me compare the expiring and proposed policies. “Tell me the key differences between these two documents.” was the prompt I used to get ChatGPT to compare the two documents and give me a list of talking points for this “volume over quality” agent. It returned a clean, structured summary of differences – including those the industry association’s own insurance agent couldn’t even explain to me. Note that I didn’t get ChatGPT to make a specific recommendation on which policy I should pick. I just wanted to understand the policies better without slogging through hundreds of pages.

The verdict: Do use Chat GPT to outline differences between long insurance contracts, or other long, legal documents. You’ll still want to double-check anything legal or binding, but this is one of the most reliable use cases we’ve found – identifying the differences.

Chat GPT can be a little too eager to please, but it can be incredibly useful if you know when and how to use it.

Use Case #3: Financial Analysis

When it comes to financial statements or profit-and-loss breakdowns ChatGPT is still hit or miss. It’s not a replacement for a trained accountant. But it can be a powerful assistant – especially when used with very specific prompts.

For example, account reconciliation often means matching transactions across records. A prompt like “Find this exact amount in this account and show me which transactions add up to it in another” can be a huge time-saver. I used this successfully while reviewing clearing accounts for a client.

This use is honestly quite similar in principle to Use Case #2 above – just with large accounting data sets. In the same way you avoid having to read hundreds of pages, you avoid having to go line by line to find transactions that appear in both data sets.

The verdict: ChatGPT’s strengths in financial analysis lie in supporting accounting resources via pattern recognition and number matching—as long as the target is clearly defined in the prompt.

Use Case #4: Writing Tough Emails

Need to send a firm but kind customer response? End a vendor relationship? Follow up on an overdue invoice? Small business owners can send 40-60 emails per day when managing multiple client accounts, proposals, vendor relationships, etc. Having ChatGPT draft head starts for these emails can save you serious time. It can even give you versions with different tones: professional, empathetic, assertive. That way you’re not starting from scratch every time.

Those of you that know me well know I can be, well, a bit blunt at times. ChatGPT does a great job of taking the “jerk” out and putting more of the “sweet” in what could otherwise be a “rude Jeff” email.

The verdict: Put your own personal spin on important email communications, but let ChatGPT handle the rough draft to speed things up.

Use Case #5: Letting ChatGPT Stand In As A Human To Role Play A Scenario

If you’ve ever rehearsed a conversation in your head before actually having it, this one’s for you. Whether it’s negotiating pricing with a vendor, delivering feedback to an employee, or explaining a policy to a difficult customer, ChatGPT can play the other side of the table. You feed it the context, and it gives you a practice run. It won’t replace your instincts or make you more empathetic, but it will help you hear how your message lands—and maybe avoid saying something you’ll need to walk back later.

The verdict: ChatGPT won’t replace emotional intelligence or good leadership judgment—but it can help you organize your thoughts and approach challenging conversations with more confidence and clarity.

Use Case #6: Personal Productivity & Planning

This one’s not strictly business-related—but let’s be honest, most small business owners don’t have a clean line between work and personal life anyway. I’ve found ChatGPT pretty useful when I need to make a decision quickly and don’t want to spend 45 minutes falling down a Google rabbit hole. Need vacation ideas? I got 80% of my family’s 2024 DC vacation plans from about 5 minutes spent on ChatGPT. ChatGPT had the idea to hit Arlington on the way in. ChatGPT had the idea to park the car for 4 days and walk or subway everywhere in DC proper. Chat GPT had the idea to build in a couple blank, half day slots for rest, rain, or on the fly ideas. None of these were earth-shattering; but I didn’t have to think of any of them.

Shopping for something and have no idea where to start? Ask for the top-rated options under $X with pros and cons. No, it won’t give you the perfect answer. But it’ll get you most of the way and save you the headache of reading through all the reviews!

The verdict: A solid time-saver for personal planning and everyday decision-making—especially when you just need to get unstuck and move on.

Warning: Don’t ignore ChatGPT’s own warning underneath it’s own search bar: “ChatGPT can make mistakes. Check important info.” ChatGPT has been known to immediately repeat back incorrect information, for seemingly no reason, when it has just been given all of the information it needs to know the answer. That’s concerning. In fact, we’ve seen this happen a lot. It also “hallucinates” as many people have been known to call it, making up facts out of thin air. Don’t just proofread what ChatGPT gives you, remember that your own human knowledge is still really valuable, and to trust that over what AI is telling you.

ChatGPT isn’t magic. It’s not going to think for you or run your business while you sleep. But it is a useful tool—especially if you’re willing to experiment and give it clear direction. The key is treating it like a junior team member with potential: helpful, fast, and surprisingly capable at times—but not someone you’d hand the reins to without oversight. If you’ve tried ChatGPT once and didn’t see the value, try again with a more specific, practical use case. Odds are, there’s a spot in your workflow where it can quietly save you time or help you think a little more clearly.