The AI Paradox: Why It's Both Your Best Assistant and Worst Enemy
How the same tool that drafts your motion in minutes can confidently cite cases that don't exist - and what every lawyer needs to know before trusting AI with legal work
If you’ve experimented with AI tools like ChatGPT or Claude in your practice, you’ve probably experienced both sides of what I call the AI paradox.
On one hand, these tools can draft a comprehensive motion in minutes that would normally take you hours.
On the other hand, the tool will cite cases that don’t exist - presenting both outputs with the same level of confidence.
As I demonstrate in the video above, this isn’t a theoretical challenge - this paradox is evident whenever you use AI.
And understanding where AI succeeds versus where it fails isn’t obvious until you dig deeper.
The Real Power (It’s Not Hype)
Let’s start with what AI genuinely did well in the video:
20 well-structured paragraphs of factual background
Over 100 paragraphs of legal analysis with proper organization
Clear section headings and logical flow
Strategic arguments organized coherently
All within the span of minutes.
AI clearly excels at taking information you provide and organizing it into professional, structured documents. For first drafts, it’s genuinely exceptional.
This isn’t just impressive: it has the potential to transform lives for lawyers managing heavy workloads. Those hours saved on drafting are hours you can spend with clients, on strategy, or simply with your family.
Where the Wheels Come Off
This strength in organizing and pattern recognition is AI’s biggest weakness when it come to finding information is relevant.
Case in point: I asked for relevant Ontario case law. AI confidently provided 49 cases with proper citations.
They looked perfect at first glance - party names, years, court abbreviations, citation numbers. On closer scrutiny, more than 50 % of the cases discussed in the video were problematic:
Some cases existed but were not relevant (criminal matters when I needed arbitration law)
Some cases simply didn’t exist at all - pure fabrications that followed the right citation format
Even more concerning? When I asked AI to verify its own citations, it claimed it had confirmed all the links were accurate. The truth was that it hadn’t - it actually did not even have the ability to access the legal database.
Yet the tool told me everything was verified anyway.
Understanding What’s Actually Happening
This isn’t a bug. This is how AI fundamentally works.
AI is designed to be helpful, which means it will give you an answer even when it should say “I don’t know.” It fills gaps with confident-sounding fabrications rather than admitting uncertainty.
So in my arbitration example, AI knew my objective, recognized what legal citations look like (Party v. Party, Year, Court, Number), and simply created cases that matched both the format and my desired outcome.
The cases sounded perfect because they followed the right pattern and matched my needs - even when they didn’t exist.
This is the paradox: The same tool that makes you incredibly efficient can also make you dangerously wrong.
Again not a theoretical issue as the many real-life cases makes clear.
One lawyer’s time-saver becomes another lawyer’s career-ending mistake.
The Strategic Integration Approach
The solution here isn’t to abandon AI. That would be like refusing to use computers because they can crash.
Instead, you need to understand where AI excels and where human expertise is non-negotiable.
Leverage AI for:
First drafts of factums, motions, and memoranda
Organizing complex information into logical structures
Generating multiple approaches to arguments
Summarizing lengthy documents
Creating templates and frameworks
Never rely on AI for:
Legal research and case citations
Verifying factual accuracy
Jurisdictional-specific analysis
Ethical judgment calls
Final work product without review
Building a Sustainable Practice with AI
The lawyers who are succeeding with AI aren’t using it to replace their judgment - they’re using it to amplify their capabilities while maintaining control.
They let AI handle the time-consuming structural work, then they apply their expertise to verify, refine, and perfect the output. This is the integration approach: technology enhances your practice without compromising quality or ethics.
This is exactly the kind of strategic thinking that creates sustainable practices. You’re not working harder or taking shortcuts—you’re working smarter, using tools that free up your time for the work that actually requires your legal expertise.
Taking the Next Step
You’ve seen exactly where AI can help your practice and where it can hurt it. Now you need to decide how you want to move forward with this knowledge.
I’m hosting a hands-on workshop specifically for subscribers who want to use AI strategically in a way that fits into your actual workflows.
Every Substack subscriber can join the complete live workshop and get the full training, see real demonstrations like the one in this video, and ask questions during the session. The only constraint is timing - you need to be there live.
If you can make it, you’ll get everything you need to start using AI more confidently in your practice.
One thing I’ve learned from my use of AI is that the real transformation doesn’t happen during the live session. It happens in the days and weeks after, when you’re actually implementing what you learned and questions come up.
That’s where paid subscribers get a significant advantage in getting the support you need to build a complete implementation system. Paid subscribers get
The workshop recording that allows you to revisit specific sections when you’re ready to implement that particular workflow.
Our prompt template library means you’re not starting from scratch trying to figure out the right way to phrase things.
Our monthly Q&A sessions means when you hit a roadblock during implementation, you’ve got support.
Access to future workshops means you’re continuously updating your skills as AI capabilities evolve.
The live session gives you knowledge.
The paid membership gives you implementation support.
Both are valuable, but only one actually transforms your practice.
The investment is less than one billable hour for a full year of access.
The time you’ll save using the prompt templates in your first week will more than cover it.
And the mistakes you’ll avoid? Those are worth far more than the subscription cost.
Remember: AI is transforming legal practice whether you’re ready or not. The question isn’t whether to learn it—it’s whether you’ll learn it safely, strategically, and with expert guidance, or through expensive trial and error.
What’s been your experience with AI in your practice so far?
Hit reply and let me know - I read every response and often use them to shape workshop content.