Sharp (AI) Tools Don’t Forgive Wishful Thinking: What Avocado Pits and AI-Powered Contracts Teach Us About Risk, Readiness, and Leading With Clarity

Hello Friends and Colleagues,

Recently, I found myself in the kitchen, alone. That never happens. Everyone in my house loves to cook. I made an early decision not to compete in that culinary arena. Let them have the red waters of who cooks it best. I happily swim in the blue waters of taste-testing what they make.

But that day, I wanted an avocado toast. A great one. The kind I hunt down in cafés with unreliable Wi-Fi and overly enthusiastic menus. Rustic bread. Perfectly ripe avocado. A touch of lemon and sea salt. Maybe microgreens, if I’m feeling smug.

I cut the avocado. Then, ignoring better judgment, I went after the pit with a very sharp knife.

You know what happened next.

A few hours and several stitches later, the doctor raised an eyebrow and said, “Well, the good news about weapon training is if you survive it, you tend to get better.”

It was meant as a joke. But it landed like a lesson.

Because what I really walked out of that ER with wasn’t just a bandage. It was a reminder: sharp tools don’t tolerate overconfidence. And AI is no exception.

AI is a Sharp Knife

Like a blade, AI is powerful. And like a blade, it doesn’t care how confident or optimistic you are when you use it. What matters is whether you’re trained. Whether the tool is right for the task. And whether you understand the risk of using it wrong.

This is exactly what we’re tackling with Coach Frankie, the AI-powered Product Law Coach, built with Adrienne Go, my brilliant co-founder. Coach Frankie is already in beta testing at University of California, College of the Law, San Francisco (formerly UC Hastings) and University of California, Berkeley - School of Law . The feedback from digitally native future lawyers has been insightful, generous, and occasionally tough. And we welcome it. Coach Frankie is improving quickly. She’s not just sharper and more helpful. She’s getting lipstick!

Coach Frankie doesn’t replace legal expertise. She accelerates it. She helps lawyers build sharper judgment, faster. Spot risks earlier. Speak stakeholder. And become the kind of product counsel teams trust before they know they need you.

Soon, we’ll be opening Coach Frankie to more testers beyond the two law schools. If you want early access to the program and to earn the certificate, you can sign up here: Join the Early Access Program.

You Can't Use AI Safely Without Benchmarks

One of the most reckless things I did with that avocado was assume my instincts were good enough. I had no benchmark. I didn’t check in with anyone. I didn’t ask, “Is this the right way to do this?” Is stubbing an avocado seed mid-flight with a sharp knife a good idea? Probably not. Was weapon training needed? Probably yes.

Legal professionals are falling into that same trap with AI and contracts.

That’s why I’m not just watching the rise of third-party contract benchmarking; I’m actively building it. Tools like TermScout’s Predict and Certify are redefining how legal teams assess risk and fairness. Data matters, especially when it’s delivered in the right amounts, to the right people, at the right moment.

You don’t have to guess whether indemnities are off-market. You don’t have to assume liability caps are standard. You don’t have to hope a vendor’s SLA aligns with peers. Now you can know.

Third-party benchmarking uses real-world data to measure contract terms before signature. With Certify trust badges and favorability scoring, you walk into negotiations with intelligence, not assumptions. And with Predict, you know which clauses will raise eyebrows before the first redline lands.

If you haven’t read it yet, I strongly recommend starting with this piece by Milada Kostalkova : Third-Party Contract Benchmarking: Reducing Risk Before You Sign

Then go deeper into how this fits into a bigger shift: Legal Data Intelligence: Transforming Insights into Action

The takeaway is clear. Legal teams can’t wait for perfect tools or perfect policies. We need better visibility. Better guidance. Faster pattern recognition.

Curious how your contracts compare? Explore the platform and see what actionable data can unlock.

Sharper Tools. Better Outcomes. Trusted Counsel.

When lawyers understand how their advice stacks up against peers, the market, and the pace of business, they become something far more valuable than issue-spotters. They become decision partners. When they benchmark, they reduce noise. When they train with context, they reduce risk. And when they combine AI with good judgment, they accelerate trust.

Like the sharp knife I grabbed too confidently, AI does not reward optimism. It rewards readiness. Legal professionals do not need to be AI experts, but we do need to know when the blade is too close to the pit and how to choose tools that guide, not gamble.

Practicing law today means building systems, not just spotting issues. The tools we need must do more than speed things up; they must sharpen how we see risk, guide how we give advice, and reflect how business actually works. What matters now isn’t perfection. It’s moving forward with tools that bring context, precision, and momentum to your work.

Until next time, lead with clarity, act with precision, and keep testing with intention.

Warmly,

Olga

P.S. The finger is intact, but it now doubles as a cautionary tale. Like most legal missteps, it didn’t come from malice, just overconfidence and a lack of a benchmark. Lesson learned: sharp tools don’t forgive wishful thinking.

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Olga V. Mack is a leading innovator in the legal field, driving digital transformation and championing the use of technology to modernize law. With a focus on efficiency, accessibility, and client-centric solutions, she has redefined traditional legal practices through groundbreaking tools, strategies, and advocacy. As an award-winning CEO, General Counsel, accomplished author, and sought-after thought leader, Olga is dedicated to empowering the legal profession to embrace transformative technologies and stay adaptable in an ever-evolving world.