How to Use AI to Prepare Your Business for Sale

Not long ago, one of our co-founders worked on a deal that looked like a dream: a business doing about $1 million in revenue, under contract for $4.8 million with two experienced buyers.

Then diligence started. The buyers spent weeks inside the business and realized everything ran through the owner, from every customer relationship to every operational process.

First, the buyers cut their offer to $4.2 million. Then, as their doubts kept growing, they walked away entirely. When we brought the business back to market, the offers came in far lower.

This is just one example of owner dependency, one of the most common problems we see when businesses go to sell, and one that AI is remarkably good at fixing. The catch is that most owners don't know how to use it that way. 76% of small businesses are already using AI for things like flyers, emails, and invoices, yet 73% say they'd benefit from more training and resources to use it well.

To help small business owners get started with AI, we invited Pat Miller, owner of the Small Business Owners Community, to show us how Claude can get a business out of its owner's head by documenting and automating the workflows that keep owners tied to their businesses. The payoff works on two timelines at once: an easier week right now, and a business that's ready to hand off whenever you decide it's time.

The case for treating AI like a new hire

The first step is a mindset shift. Most business owners approach AI as an intimidating super-intelligence, and they feel a kind of guilt when they can't get impressive results out of it right away. Pat suggests thinking of it instead as a junior employee.

A new hire is promising and capable, but on their first day they don't know your business, your customers, or how you like things done. You wouldn't expect great work before you've onboarded them. AI works the same way: give it access to your information, show it what a good result looks like, and hand it one task at a time. The results improve as its understanding of your business grows.

The result is the difference between a chatbot and a connected assistant. A standalone chatbot can answer any question you bring to it, but you have to carry the answer back out and paste it wherever the actual work happens. A connected assistant can see your email, files, calendar, and apps, and can do the work where it lives: drafting the email in your inbox, updating the record in your CRM, and pulling the numbers from your bookkeeping software. That connection is what turns AI from a novelty into something that genuinely takes work off your plate.

Six steps you can take this week

The best way to build momentum is to start small. Each of these steps takes an afternoon or less, and they work whether you use Claude, ChatGPT, Gemini, or another tool.

1. Connect your core software. Start with four things: your documents (Google Drive or OneDrive), your email, your calendar, and wherever you keep your to-do list. Together, these let your assistant see who you're communicating with, what you've written, where you need to be, and what needs to get done. Everything else (bookkeeping, CRM, design tools) builds on that foundation.

2. Have it build a profile of your business. Once it's connected, ask it to read through your documents and email and answer questions like: How do I make my money? Who are my clients, and what do they have in common? Where am I growing, and where am I shrinking? You don't need to write a perfect prompt. Describe the outcome you want and let it work. Pat saved the result as a reference document he loads whenever he starts a significant task, so the assistant always begins with full context.

3. Ask it for perspective, not just tasks. This is the step most owners skip, and Pat believes it's where the most value hides. Ask questions like: What are clients repeatedly asking about that I'm not currently selling? Where do customers get stuck? Where are my employees frustrated, and what could I fix for under a thousand dollars? Because the assistant can read across your entire business at once, it will notice patterns you've missed. Pat says its observations have helped him find new business lines.

For instance, if you're thinking about selling, ask your AI assistant to play the role of a skeptical buyer evaluating your business. Have it ask you the hard questions a real acquirer would ask about owner dependency, discretionary earnings, customer concentration, and documentation. Then have it build an action plan to address the weaknesses it finds, and set it to check your progress against that plan every week.

Pat compared it to going to the gym: the value comes from doing it consistently, well before you need the results. Every question that exercise forces you to answer now is a question a real buyer won't have to worry about later, which means a smoother diligence process, a stronger price, and a much better chance your deal actually closes.

4. Let it interview you. If you don't have years of written content for the AI to learn from, don't worry: you're carrying more knowledge than you think. Ask the assistant to interview you about your business, one question at a time, and answer out loud using voice dictation. Fifteen or twenty minutes of conversation produces enough raw material for months of blog posts, emails, and social content. Meeting recordings and your sent email folder are also rich sources.

5. Save your best results as repeatable instructions. When you've gone back and forth with the AI and the result is finally right (a newsletter format, an email style, a report), ask it to turn that conversation into a saved skill. From then on, it will produce that work the same way every time, without you re-explaining. Pat trained one on 200,000 words of his own show transcripts so it writes in his voice, though he notes he still reviews everything before it goes out. Knowing when to keep a human in the loop is part of using these tools well.

6. Put the repeatable work on a schedule. Saved skills can run automatically: a morning briefing before you wake up, a background scan of your inbox for suspicious links, a research dossier prepared before every meeting. Once that happens, AI stops being something you operate and starts being something that works alongside you.

The catches

If you work with regulated information (medical records, legal matters, client financials) check your industry's compliance rules before connecting anything, and consider anonymizing data the way some of Pat's financial advisor clients do.

Also remember to budget realistically: entry-level plans around $20 a month won't get you far, and Pat recommends serious users start around $100 a month. He thinks of the cost as a personnel expense rather than a software subscription, which makes it feel like a bargain.

Finally, expect some rough edges. You may run into occasional hiccups when new versions roll out, platforms like LinkedIn that restrict AI access, and video editing that isn't quite there yet.

Final thoughts

The same work that gives you back your Fridays is the work that makes your business sellable. Every workflow you document, every process you automate, every piece of knowledge you move out of your head and into a system makes your business easier to run today and easier to hand off tomorrow.

Wondering what your business is worth right now? Every Baton sale starts with a free valuation, including honest feedback on what would make your business more valuable to a buyer. It's the clearest picture you can get of where you stand and the first step toward a business that's ready to hand off whenever you are.

FAQ

What are AI agents for small businesses?

An AI agent is an AI assistant that's connected to your actual business tools (email, documents, calendar, CRM, bookkeeping) and can do work inside them, rather than just answering questions in a chat window. Instead of copying an AI's answer into your inbox, an agent drafts the email in your inbox. That connection is what makes AI useful for day-to-day operations, not just brainstorming.

Which AI is best for small business?

Pat uses Claude, and switched from ChatGPT when Claude's Cowork feature launched because it was the first tool that connected all of his business software in one place. But his honest take is that the major platforms (Claude, ChatGPT, Gemini) are converging on similar capabilities. The best AI for your small business is the one you'll commit to: pick a platform, connect it to your tools, and get fluent with it.

How much does AI cost for a small business?

Entry-level plans run about $20 a month, but they won't get you far once you're doing real work. Pat recommends serious users budget around $100 a month; he runs his own business on a $200 plan. His advice is to treat it as a personnel expense rather than a software subscription. Compared to even a few hours of an employee's time each week, it's a bargain.

Can AI really reduce owner dependency in a business?

Yes, that's arguably its most valuable use for anyone who plans to sell someday. Every workflow you document and automate with AI moves knowledge out of your head and into a system a new owner could run. That directly addresses the top concern buyers raise in diligence: whether the business can operate without its current owner.