TL;DR
- Most small business owners using AI are barely scratching the surface – copy/pasting email responses and calling it done
- A blank screen after an AI overview is not training. Specific use cases tied to real business problems are.
- One session using ChatGPT and Claude produced a BNI 32-second commercial, a cartoon handout for her members, and a list of business-specific prompts she can use starting today
- There is still more to come – batch-processing newsletters, creating reports from data, and setting up Claude to write in her voice
- This is the kind of work I am building a service around – AI training for small and mid-sized businesses, uniquely created for each owner
My accounting client had been using Microsoft CoPilot for about six months. Her only use case:
- copy and paste emails she didn’t have time to respond to,
- CoPilot drafted a reply,
- paste response,
- and move on.
That was it.
She knew AI existed and figured it was supposed to help her somehow. She had no idea what she was actually sitting on.
We changed that last Saturday in three hours and that was just the beginning.
What “Just Using AI” Actually Looks Like
CoPilot is a capable tool. But six months in, my client was using it the way most small business owners use AI – as a slightly smarter search engine. Ask a question. Get an answer. Done.
The problem with that approach is that it leaves 90% of AI’s actual usefulness untouched. AI is not just a question-answering machine. For a small business owner, it can be a writing partner, a research assistant, a speech coach, a content creator, a report generator, and a time-savings engine – if someone shows you specifically where to point it in your own specific business.
Nobody had done that for her. She had a tool and no map.
Starting With the Blank Screen Problem
The first thing I did before we ever got on a Zoom call was to have a conversation with her about what was frustrating her in her business – specifically. That time became the foundation for a custom reference resource I built for her that included:
- Use cases tied directly to the challenges she spoke about
- Starting prompts she could copy and use immediately
- A comparison table showing when ChatGPT is the better tool and when Claude wins
That reference document is what she opened the session with. Not a blank screen and a “good luck.”
The goal was to give her a running start, not a textbook.
What We Actually Did in Three Hours
We set up both ChatGPT and Claude. I walked her through my Special Instructions setup – specific configurations that reduce hallucinations, prompt the AI to give additional useful context after every output, and make responses more useful from the first message.
I showed her how I use multiple AI tools together to build consensus on direction and when best to use that strategy. One AI alone can be confident and wrong. Running the same problem through two or three and comparing outputs is a much smarter approach for anything that matters.
I gave her a tour of my own work – how I use ChatGPT, Claude Chat, Claude Code, Claude Cowork, Gemini, and Grok. I showed her my Substack The Cautious Modernizer – specifically Issue 02: The Adoption Problem Nobody Wants to Name – so she could see my beliefs in action: humans drive AI, humans drive AI. AI does not replace them.
I shared several prompts I have collected for getting brutally honest feedback from AI. These are not my original creations – I picked them up from other practitioners and tested them. They include:
- Devil’s Advocate – forces the AI to argue against your idea
- Red Team – attack-mode analysis of a plan or decision (Grok is particularly brutal with this one, which makes it especially useful)
- Gordon Ramsay – no-filter critique of your work
- Third-Party Framing – gets the AI to evaluate your work as an outside expert would
- Grading Itself – asks the AI to score its own output and explain the gaps
For a business owner who has been getting polite AI responses that feel helpful but miss problems, these prompts are a different experience entirely.
The BNI Commercial She Delivered This Week
Every week, members of BNI – a national business networking organization – deliver a 30-second commercial and occasionally an eight-minute speech to their chapter. The commercial is one of the most repeated, most practiced pieces of communication a small business owner in BNI does. My client had both the 30-second commercial and an eight-minute speech coming up.
We used both of these as a live training exercise.
She gave Claude the context. We worked through the speech and a pitch deck (PowerPoint) together – using AI to draft, refine, and sharpen the message. Then we took it one step further. We used ChatGPT to create a cartoon-style handout for her eight-minute speech she could print and distribute to her members. The handout illustrated each myth she was busting in the speech, one by one.
During this time, she got to see a real case use, the real nuances of working with AI, and the limitations of the free and lower cost plans.
She walked out with a finished commercial, a speech nearly done, and a printed leave-behind – all in three hours. She upgraded her Claude account after the session and finished the speech the same day.
What She Said an Hour After We Hung Up
Sixty minutes after our Zoom ended, her feedback texts came in.
She had already upgraded her Claude account and used it to start prepping social posts for her next presentation.
“OMG! When in upgraded, finish the presentation going to send you a Facebook post and a LinkedIn post for the day before and the day of. Already wrote my 30-second commercial for this coming week because it’s going to be the hook that tells people what’s coming. Having way too much fun!”
I could live in Claude land
Anything that’s going to help me make my life a little bit easier it’s huge.
I really do appreciate your time and energy and all the thought into this thank you so much.
You don’t know what you don’t know. There are a lot of small business owners out there trying to figure out what to use what not to use how to use it what it what works best what doesn’t work best I mean I’ve only eaten using CoPilot for a few months maybe six.
Six months of CoPilot copy-paste. Three hours with the right map. She already knew the difference by the time she put her phone down.
What Is Still Coming
We did not get to everything. That was intentional – I did not want to overwhelm her in session one.
In future sessions, she will learn how to use Claude Cowork for batch-processing summaries of the e-newsletters she never has time to read. The demo I showed her – where I had Cowork read 86 emails, follow links to blog posts, and produce summaries with action items – is something she can use on the exact backlog sitting in her inbox right now. She will learn how to use it for creating reports from batch documents into her output of choice – PDF, Excel, or Word.
We will also set up Claude skills to write in her writing voice, know her business inside and out, and understand her target audience. That setup takes two to three hours of focused prompt work, but once it is done, Claude stops feeling like a generic tool and starts feeling like someone who has been briefed on your business. Claude skills really is the AI gamechanger.
This Is the Service I Am Building
I am not a corporate-level AI user. I am not an engineer developer. I am a 25-year webmaster veteran who has been working in and around small and mid-sized businesses long enough to know exactly where the gaps are – and exactly how to fill them without turning a business owner into a technologist. I jumped into learning AI within one month of ChatGPT’s release and within one month of that was already teaching people how to use it in their businesses.
The AI training I am building under Webmaster For Hire is one-on-one, custom to each business, and paced so it actually sticks. Not a $50 a month, generic training video that is obsolete five days after release. The goal is AI actively working on your specific business problems, starting in session one.
My accounting client is proof it works after session one.
If you are a business owner sitting on AI tools you barely use – or not using them at all because nobody has shown you where to start – that is exactly who this is built for.
AI integration is already part of the Digital Oversight Partnership. If you are a DOP client, we are already building this together.
If you are not a current client but want one-on-one AI training for your business, contact me to get on the list. Pricing and session details are coming soon.
Ready to Stop Staring at a Blank AI Chat Screen?
Individual AI training sessions for small business owners are available now. Contact me to talk through what your business needs and where we would start.
And if you want to follow along as I document the human side of AI adoption, technology decisions, and digital oversight for small business owners, my Substack The Cautious Modernizer covers exactly that – no hype, no developer-speak, no ‘AI will replace you’ panic. Just a straight look at what modern technology can actually do for the businesses running this economy.
