Lawyers Cannot Afford to Trust AI Blindly
A Fortune article this week revealed something fascinating: Claude Sonnet 4.5, one of the most advanced AI models available, experiences what researchers call “context anxiety.” When approaching its processing limits, it starts cutting corners, rushing through tasks, and leaving work unfinished—even when it actually has plenty of capacity left.
Sound familiar? It should. Because if the most sophisticated AI gets nervous and makes mistakes under perceived pressure, what does this tell us about relying on AI for mission-critical work?
This is exactly why AI should augment your work, never replace your judgment.
We’ve already seen the consequences when lawyers treat AI as a magic button. Remember the attorney who submitted a brief filled with completely fabricated case citations generated by ChatGPT? Or the lawyers sanctioned for filing motions citing non-existent cases? These weren’t hypothetical risks—they were real sanctions, real embarrassment, and real damage to client relationships.
The Fortune article’s findings about Claude’s context limitations add another layer to what we already know: AI tools have limits, blind spots, and failure modes that aren’t always obvious. Even when they appear confident, they can be wrong. Even when they seem thorough, they might be cutting corners you can’t see.
This is why I’ve upgraded my AI tool subscriptions: not to rely on them more, but to mitigate the risks associated with using them to augment my research and due diligence. Larger context windows and advanced features help, but they don’t eliminate the need for human oversight.
For my fellow attorneys (and business leaders), here’s what this means practically:
- Always verify. Every case citation, every legal principle, every factual assertion. No exceptions. AI doesn’t have a law license—you do, and your name is on the work.
- Use AI as a starting point. Let it draft that first outline, summarize that deposition, or brainstorm arguments. Then apply your expertise to refine, verify, and improve it.
- Understand the tool’s limitations. Know what your AI can and can’t do. Check those context windows. Be aware that quality can degrade in long documents or complex tasks.
- Stay current on competence requirements. Professional responsibility requires that we understand the technology we use. Ignorance isn’t a defense when AI goes wrong.
- Build verification into your workflow. Create systems where AI output goes through review checkpoints before anything client-facing goes out the door.
The Fortune article is a powerful reminder of why the human element remains irreplaceable. Use these powerful tools. Let them make you faster and more efficient. But never, ever let them replace your professional judgment.
AI is here to stay. The question is, are you using it wisely?
#TravelNotes. A statue of Richard Seddon, who opposed women’s voting rights, points toward the Kate Sheppard Apartments, named after the woman who helped win women the vote. A local guide pointed this out during my birthday trip to Wellington, NZ.
I came across this photo while sorting through images for my upcoming workbook for leaders building human-first organizations in an AI-powered world. I’m sharing it here because the story behind it reminds me of my work at UpwardAction Advisory ~ helping leaders see what they’re actually looking at when building use case scenarios.
We cannot design the future if we misunderstand the past or ignore what is standing right in front of us. Like the statute in this photo, leadership often faces forward while pointing backward. Awareness changes everything.#Trvel
I was reading the Pew Research report last week and it confirmed what I’ve been hearing all summer in conversations with folks in Lisboa, Porto, Vienna and across the US.
The data is clear. 53% of Americans believe AI will worsen our ability to think creatively. Concern about AI in daily life has jumped from 37% to 50% since 2021.
While people are right to be concerned, their fears do not reflect an inevitable outcome. The gap between AI making us our most creative selves and our laziest selves comes down to how we choose to use and integrate this technology into our work and lives.
Vienna and the Promise of Augmentation
I was in Vienna during TEDAI Vienna, Europe’s official three-day TED Conference on AI that ran September 24-26. While I didn’t attend the conference itself, being in the city during that time sparked fascinating conversations with leaders working on AI governance in the EU.
What struck me most was our shared excitement about what AI makes possible when used strategically. We all felt the same sense of responsibility to help companies and leaders understand how AI can and should augment human capability, not replace it.
These conversations felt urgent and hopeful in equal measure.
The Lisboa and Munich Warning
The Vienna conversations stood in sharp contrast to what I heard earlier this year in Lisboa and Munich. I spoke with several digital nomads, freelancers working for large companies, who were frustrated and fed up. They weren’t complaining about AI itself. They were complaining about their direct contacts at these companies.
Middle managers, in their words, were “dumbing down” their work through an over-reliance on AI without ever using AI well. These managers were accepting AI-generated first drafts as final products. They were outsourcing judgment to algorithms without adding strategic thinking. They were cutting corners instead of creating leverage.
The freelancers could see it happening in real time. Quality declining. Creative thinking evaporating. Strategic value disappearing.
And here’s the thing that made it worse: the middle managers using AI this way weren’t even aware they were doing it. They thought they were being efficient. They thought they were keeping up with innovation. They were actually falling behind while dragging their teams down with them.
Don’t Be That Kind of Leader
AI becomes dangerous and ultimately counterproductive when we let it replace our thinking rather than augment it. When we accept the first draft as the final version instead of using it as a starting point to expand our thoughts and perspectives. When we outsource judgment instead of using AI to sharpen it by challenging our assumptions and uncovering undeveloped hypotheses.
AI can be your strategic advantage if you use it to augment, not replace. Let the technology handle the basics so you can focus on what requires human brilliance. Use it to test ideas, strengthen arguments, and expand your thinking. Utilize AI to automate mundane tasks, allowing you to focus on innovation and vision.
AI does not have vision. You do.
This truth applies whether you’re leading a law firm, running a business, or managing a team. Do not ignore AI or use it as a crutch. Let the technology elevate your capabilities, not diminish them.
The Choice Is Yours
I support leaders in developing use cases that make AI work for augmentation, not replacement. Use cases that unlock creativity, boost productivity, and create efficiencies that matter. The future belongs to those who know how to pair human creativity with technological power.
Use, train, and encourage your teams to use AI strategically and creatively, not lazily. The digital nomads in Lisboa and Munich were watching their work get diminished by leaders who didn’t know better. Your team is watching you too.
Want to continue this conversation? Follow me and connect on LinkedIn at linkedin.com/in/iamcoachtc where I share insights on AI strategy, global leadership, and creative augmentation.
Read the full Pew Research report: How Americans View AI and Its Impact on People and Society
Bridges are among my favorite things to photograph. I am fascinated by the vision, courage, and skill it takes to build them.
This photo that I took of the Dom Luís I Bridge in Porto, Portugal is one of my favorites. Completed in the late 1800s, it was once the longest iron arch bridge in the world. Standing on it, you cannot help but notice how intentional design, engineering excellence, and bold imagination combine to create a lasting stucture that makes connection easier.
Systems as Bridges
In business, systems function much like bridges. They connect tasks, teams, and technology in ways that increase productivity, profitability, and impact. When designed with care and aligned with values, systems become bridges to growth and clarity.
Here is the tension — systems & technology only work when they are rooted in values. A poorly designed bridge is unsafe. A system without alignment creates risk, wastes time, and drains energy.
Technology in Service of Values
The leaders thriving in today’s world of emerging technology are not chasing every new tool. They are grounding themselves in values and letting technology serve those values. Artificial intelligence can automate repetitive work and organize information, but its true power lies in freeing people to do what only humans can: build trust, exercise judgment, and make values-driven decisions. This is how profitability goes beyond money. Well-built systems create space for flourishing in organizations, teams, and lives.
A Practical Reflection
Take one system in your work today, whether financial, marketing, sales, client service, or personal productivity. Ask yourself:
- Does this system reflect my values?
- Does it create space for what matters most?
If the answers are no, it may be time to rebuild or refine. That might mean automating routine tasks, redesigning workflows, or embedding AI in a way that serves people first. The goal is not simply efficiency. The goal is alignment. Bridges remind us that building wisely is always worth it.
It was a blessing upon blessing to meet new friends in a structured way thanks to Remote Year, where we were guided by our incredible city coordinator, Viviana Alicia, and the amazing Black in Portugal (BIP) community, founded and led by Heather Protector. I also met countless new friends in coffee shops, cafés, Flamenco dance classes, as my tour guide photographer, as a passenger in so many Uber and jeep rides, and on group walking tours.
Solo travel is expansive and filled with opportunities to connect… if you want to.
I’ve done my best to live in the moment and lean into my mentor’s advice—sometimes a charge, sometimes a demand—that I walk through life’s experiences as a traveler. To be fully present in every experience, soaking in all it has to offer, rather than being a tourist passing through, snapping pictures just to say I was there.
Now, while I’ve certainly played the role of tourist this summer, I’ve also taken my desire to be a traveler seriously. I’ve allowed every experience to shape my perspective and help me see myself more clearly.
When solo traveling (which I do quite a bit), one of my favorite things is to book a tour or two—sometimes private, sometimes with others—to get a better sense of the lay of the land and learn about history from multiple perspectives. I highly recommend it.
Thanks to Airbnb experiences, I leveled up on this trip by hiring a photography-based tour in each city I visited. I did this for a few reasons: to see each city’s most beautiful or iconic backgrounds through the eyes of a photographer, to experience how different photographers interpreted my goals for the walking tours (I gave the same instructions for all five photography tours), and to have more interesting pictures for upcoming ebooks than just selfies.
I have a favorite from each photo session, and I’ll share them in future posts.
This photo is my favorite from my time in Porto for a few reasons: it’s a stunningly gorgeous shot of beautiful Porto, I walked a lot of steps to get to this location, and it symbolizes this new season of life I’m entering, where seeing the world through the lens of a traveler is a journey worth embracing.
I’m grateful for the summer and excited for the fall.
How about you?
Hey there, Leader!
Here’s your High-Performance Coaching question for this post:
Now, let’s affirm together:
Hey there, Leader ~
As we step into a brand new month, and the beginning of the second half of the year, here’s a question to help you make sure that your ‘focus’ is focused on what’s right for you.
Your high-performance coaching question for this post:
How can you use self-awareness to set goals that truly match your personal desire, rather than being influenced by what others expect of you or what you think you ‘should’ want?
Here’s what you must know about this topic:
Here’s what you must know: Deepening self-awareness is a powerful tool in helping you navigate from living to fulfill others’ expectations to living your best, most authentic life. This process is about cultivating an understanding of your genuine desires, passions, and interests, and using this knowledge to create life goals that resonate with who God created you to be.
Too often, people set goals based on societal norms, familial expectations, or perceived obligations, leading to a life that feels unfulfilled and misaligned. The transformative power of self-awareness lives in its ability to guide you in creating and pursuing goals that reflect your authentic self, not those set by external influences or expectations.
And now, for your affirmation:
My goals are a true reflection of my inner desires. I set and pursue goals that align with my authentic self, free from external influences or expectations.
Happy July!
~ Coach TC
*Image is me as interpreted by AI. L
