Luck Doesn’t Scale. Strategy Does.

Hello friends and colleagues,

Last weekend, I went to a Bruno Mars concert in Vegas. And no, this isn’t a story about music. It’s about risk. Research. And the difference between guessing and knowing.

On the way to the venue, my daughter turned to me and said, “He’s definitely going to wear black or blue. I just feel it.”

I paused. “I need more time,” I told her. “Let’s make a stop first.”

I invited her to the Versace store next to the venue.

We walked in, and three questions in, a salesperson casually mentioned that Bruno had come in a few days earlier and bought five shirts. He’d already worn blue and black the night before. That left red, yellow, and brown.

So I made my call: red or brown.

And I was right.

And that’s how I impressed my almost-high-schooler. Yep, I managed to blow her mind. With certainty, I’d get at least one shirt right. With luck, both.

As we were leaving, the salesperson waved and said, “You really know your Versace shirts.” I smiled and said, “Versace is a vibe.”

My daughter rolled her eyes, laughed, and said, “You totally made that up because you didn’t want to admit you don’t know anything about Versace shirts.”

Guilty. But that’s the lesson: It’s not about knowing everything. It’s about knowing enough to predict the next move.

P.S. I'll be at [un]CLM with Lucy Bassli on June 27. Join us as we move into a world of revenue acceleration, insight, velocity, strategy, and zero guesswork.

Good Legal Teams React. Great Ones Anticipate.

Legal work is complex. High stakes. Detail-heavy. But we often frame preparation as a burden—something to “get through.” That mindset misses the point.

Preparation is a love language. For your team. Your client. Your credibility.

We’re seeing the smartest legal and business teams reframe prep as curiosity-fueled advantage. They’re replacing instinct with insight. Redlines with readiness. Guesswork with data.

The result?

• Sales accelerates.
• Legal breathes.
• Everyone trusts faster.

You can “guess” what your counterpart wants—or you can show them that your terms are market-aligned, risk-balanced, and negotiation-ready.

You don’t need luck. You need visibility.

Read: Data Is Your Best Negotiator

The Versace Strategy: Make Research Competitive Again

Let’s stop calling it “prep.” Let’s call it what it is: Strategic pattern recognition.

Here’s a three-step playbook I use constantly:

1. Spot the tells. What clues are hiding in plain sight? A conversation, a deal pattern, a clause variation?
2. Study the patterns. What’s already happened? Who’s pushed back? Where do the roadblocks keep showing up?
3. Predict the move. Take a position based on signal, not speculation. Know the shirt Bruno’s wearing before he hits the stage.

This isn’t about obsessing over every detail. It’s about loving the details that matter, and using them to get ahead.

Zoom Out: AI + Human Curiosity = Unfair Advantage

Surfacing data is my favorite use case for AI. We see this firsthand at TermScout, AI can scan thousands of contracts and extract market norms on liability, indemnity, IP rights, and more.

But AI can’t replace you. Your questions. Your instincts. Your delight in the details.

In a world of infinite data, your edge is what you choose to notice.

What feels “off.” What’s missing. What shirt Bruno hasn’t worn yet.

That’s where strategy lives.

Explore: Contract Analysis AI: How Legal Teams Are Turning Data into Strategic Advantage

What You Miss When You’re Always On

One more thing about that concert: You had to lock up your phone at the door. No exceptions.

At first? I resisted. I wanted photos. But the truth? The absence of the phone was the gift.

We were there. Together. Fully. No screen between us and the moment.

It reminded me how distracted legal life can be. Slack pings. Late-night edits. Tabs on tabs on tabs. But real breakthroughs don’t happen in the noise. They happen in focus.

If you want to change your team’s performance, start with this:

• 90-minute phone-free blocks
• One no-email day per month
• End-of-week “deep work” hours where Slack stays silent

Small. Human. Radical.

Presence Is Performance

You don’t win trust by answering faster. You win it by showing up fully.

Smart legal teams don’t just move fast. They move with confidence. They’re rooted in data, informed by curiosity, and protected by presence.

So the next time you’re tempted to guess, don’t gamble. Prepare. And the next time you want to multitask, don’t. Be there.

Because leadership isn’t about knowing everything. It’s about knowing what matters—and giving it your full attention.

Until next time,

Olga

That’s all for this Notes to My (Legal) Self® edition. Subscribe now to get notified of each new edition, or share it with an aspiring legal leader who would find it valuable.

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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 legal tech 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.