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How to Train AI to Actually Understand Your Business | Entrepreneur

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A few months ago, I was in a strategy session with a mid-sized company that had just implemented an AI assistant to support their sales team. The promise was bold. The tool would draft personalized emails, prioritize leads and surface insights from their CRM.

Within a week, they were disappointed. The emails sounded flat. The lead scoring made no sense. The insights felt irrelevant. But the problem wasn’t the AI. The problem was the missing context.

The AI was functioning exactly as designed. It just had no idea who their customers really were, how their sales team operated or what made the brand sound like itself. They gave the system data. But they didn’t give it meaning. And in today’s AI-powered world, meaning is everything.

Related: What Is Artificial Intelligence (AI)? Here Are Its Benefits, Uses and More

Why context is the competitive edge

Most AI conversations revolve around capability: What can this tool do? Can it automate tasks? Draft emails? Forecast revenue? But capability without clarity leads nowhere.

AI isn’t here to think for you — it’s here to accelerate decisions you already know how to make. It does that best when it understands your world. That understanding is built through context.

With the right context, AI becomes an amplifier. Without it, it’s a liability.

The difference between content and context

Most businesses are producing more content than ever — blogs, emails, product pages. But content alone doesn’t move the needle anymore.

Context is what tells AI how to interpret that content. It creates structure, order and trust. It’s the invisible framework that helps AI reflect your business accurately and meaningfully.

This isn’t about writing more — it’s about designing a system that reflects the truth of your business in a way machines can understand.

The five layers of context every business needs

In my work with clients across sectors, I’ve seen one pattern hold true. The businesses that win with AI are not the ones that use the most tools. They’re the ones who master their own message and operational clarity.

These are the five core layers I help clients define and deploy:

1. Foundational clarity: What you do, who you serve, what you offer and what sets you apart — communicated consistently across every channel.

2. Customer understanding: Document the problems your customers face, the results they want and the language they use. This informs everything from prompts to positioning.

3. Brand tone and voice: AI defaults to neutral. Your job is to teach it how you sound — whether bold, technical, nurturing or direct — and embed that in your AI strategy.

4. Platform consistency: Your website, LinkedIn, press coverage and directories should tell the same story. AI builds a digital “knowledge graph” of you, and inconsistencies erode trust.

5. Process transparency
Internal workflows matter. AI works better when it understands how leads move through your system, what onboarding looks like and where handoffs happen. Without that, automation gets messy.

Related: AI for the Underdog — Here’s How Small Businesses Can Thrive With Artificial Intelligence

What this looks like in practice

I once worked with a founder who was frustrated that AI couldn’t write sales emails that sounded human. But when I looked at the prompt they were using, it simply said “Write a follow-up email to a new lead.”

That’s not a prompt. That’s a guess, so we rewrote it using their actual business context. We included who the lead was, what problem they were facing, what the founder wanted to emphasize and the kind of tone that reflects their values. The result was something they were proud to send. That’s the power of context engineering.

We are moving toward a world where AI agents will become the default discovery layer for customers. People will no longer browse. They’ll ask a question. The agent will answer. So, if your business lacks clarity, structure and contextual trust, you won’t even be in the running. But if your business is architected with context, the machine will recommend to you confidently. It will summarize you accurately. It will help you scale with integrity and speed.

The future of business belongs to the owners who take time to articulate their nuance. AI does not reward noise. It rewards clarity.

The brands that win in this next chapter will not just be visible. They will be deeply understood, and the only way to be understood by a machine is to first understand yourself.

Ready to break through your revenue ceiling? Join us at Level Up, a conference for ambitious business leaders to unlock new growth opportunities.

A few months ago, I was in a strategy session with a mid-sized company that had just implemented an AI assistant to support their sales team. The promise was bold. The tool would draft personalized emails, prioritize leads and surface insights from their CRM.

Within a week, they were disappointed. The emails sounded flat. The lead scoring made no sense. The insights felt irrelevant. But the problem wasn’t the AI. The problem was the missing context.

The AI was functioning exactly as designed. It just had no idea who their customers really were, how their sales team operated or what made the brand sound like itself. They gave the system data. But they didn’t give it meaning. And in today’s AI-powered world, meaning is everything.

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