Why Your AI Assistant Starts Making Mistakes (And How to Fix It)
Ever noticed your AI tool starts strong, then gradually becomes less helpful? Here’s what’s happening and what you can do about it.
If you’ve been using AI tools like ChatGPT, Claude, or Gemini for business tasks, you’ve probably experienced this: you start a session and the AI is brilliant. It understands your brief, generates sharp content, and offers genuinely useful insights.
But after a long conversation—reviewing documents, refining strategies, going back and forth on details—something shifts. The AI starts missing obvious points, contradicting earlier suggestions, or forgetting constraints you clearly mentioned.
You’re not imagining it. There’s a technical reason for this, and understanding it can dramatically improve how you use AI in your business.
The “Context Window” Problem
Every AI tool has what’s called a “context window”—essentially its working memory. Think of it like a desk: the AI can only work with what’s currently on the desk in front of it.
Modern AI tools have impressively large desks (some can hold the equivalent of a 300-page document). But here’s the catch: filling that desk with clutter makes the AI less effective, not more.
When you overload the AI with lengthy chat histories, verbose documents, and dozens of back-and-forth exchanges, its ability to focus and reason clearly diminishes. Industry experts call this phenomenon the AI “acting drunk”—and it’s an apt description.
What this looks like in practice:
- The AI forgets important details you mentioned earlier
- Responses become generic rather than tailored to your specific situation
- It contradicts its own previous suggestions
- Quality visibly drops compared to the start of your conversation
Why This Matters for Business Owners
If you’re using AI to draft proposals, analyse reports, plan marketing campaigns, or handle any complex business task, context overload directly impacts the quality of output you receive.
You might be paying for a premium AI subscription but getting mediocre results—simply because of how you’re using the tool, not the tool itself.
Three Strategies to Get Better Results
1. Start Fresh for New Tasks
The simplest fix: don’t treat AI conversations like ongoing email threads.
When you shift to a new topic or task, start a new conversation. If you need context from a previous discussion, briefly summarise the key points rather than continuing in the same cluttered thread.
Practical tip: Before starting a complex task, ask the AI to summarise what it currently understands about your requirements. If that summary is off-base or includes irrelevant information, start fresh with a clean brief.
2. Be Strategic About What You Include
More context isn’t always better context.
When briefing an AI on a task, include only what’s directly relevant. If you’re asking for help with a marketing email, you don’t need to include your entire brand guidelines document—just the specific points that apply.
Think of it this way: If you were briefing a human contractor, you’d give them the essentials, not dump your entire company drive on them and expect them to figure it out.
3. Break Complex Tasks into Phases
For substantial projects, work in stages rather than trying to accomplish everything in one long session.
Example workflow:
- Phase one: Strategic planning—define objectives, audience, key messages
- Phase two: Creation—draft the actual content or document
- Phase three: Refinement—review, edit, and polish
Start a fresh conversation for each phase, carrying forward only the essential outputs from the previous stage. This keeps the AI sharp and focused on the immediate task.
The Bottom Line
AI tools are genuinely powerful, but they perform best with focused, relevant context—not endless conversation histories.
By being intentional about how you structure your AI interactions, you can consistently get higher-quality outputs. It’s not about working harder; it’s about working smarter with the tools at your disposal.
Key takeaways:
- Start fresh conversations for new tasks
- Include only relevant context, not everything
- Break complex projects into focused phases
- Summarise and carry forward essentials, not entire chat histories
The businesses getting the best results from AI aren’t necessarily using different tools—they’re using the same tools more effectively.
Want to learn how AI can streamline your marketing operations? Contact Integral Media to discuss how we’re helping Australian businesses work smarter with emerging technology.
