Analogies Align Action

Hello, Friends and Colleagues,

When you explain legal concepts, do you ever feel like you’re speaking a different language? I’ve been there. Legal teams bring clarity, but too often, our advice lands like abstract theory rather than practical guidance.

The good news? Analogies can change that. They don’t just explain—they create alignment, turning legal into a natural part of the product-building process.

Let’s talk about why analogies work and how they can help legal teams connect, communicate, and collaborate more effectively.

The Art of Making Legal Click

I’ve always been drawn to structure. Maybe it’s because I grew up surrounded by it. The concrete buildings of my Soviet childhood were unapologetically functional—industrial monuments built for purpose, not decoration. Some might call them harsh, but to me, they felt like home.

Years later, I found myself captivated by a German artist who pours concrete into geometric shapes, letting the light dictate how the artwork reveals itself. I could watch this for hours. The way the structure interacts with its surroundings—the angles, the shifting shadows—feels intuitive. It reminds me of how I navigate cities, gravitating toward San Francisco’s docks, with their iconic cranes, abandoned factories, and refineries. There’s something familiar in their unpolished efficiency. No pretense. What you see is what you get.

And maybe that’s why I love analogies. They are the straight lines of communication—the shortest distance between A and B. They strip away the unnecessary and make the abstract feel concrete.

That realization changed how I approach legal work.

Why Analogies Work

Simplify Complexity, Build Trust

Legal teams don’t just provide rules—they shape how organizations make decisions. But too often, our guidance feels theoretical. Analogies help bridge that gap by connecting legal principles to things people already understand.

Three Reasons Analogies Are So Effective:

• They Make the Abstract Concrete Regulations, risk, compliance—these concepts can feel like distant, invisible forces. Analogies give them form.

Example: I once had to explain GDPR’s data retention policies to a product team at an online dating company. I told them:

"Holding onto old user data is like saving all your ex’s photos after a breakup. It’s best to delete what’s no longer needed to move forward responsibly."

That clicked. Instead of seeing data retention as a bureaucratic rule, they saw it as part of a natural, necessary process.

• They Build Alignment Across Teams A well-chosen analogy turns legal from a last-minute obstacle into a collaborative force. When teams grasp the “why” behind legal guidance, they internalize it—and that’s when real alignment happens.

A fintech team expanding into a new market saw regulation as an obstacle. I reframed it:

"Legal risk is like managing liquidity. Some volatility is expected, but the goal isn’t to eliminate movement—it’s to stay fluid. Just as you hedge financial risk, you structure compliance to absorb shocks without disrupting momentum."

That shifted their mindset. Regulation wasn’t a roadblock—it was something they could navigate strategically.

• They Encourage Action A great analogy doesn’t just explain—it drives decisions.

Example: I once was advising a fintech team that built a cutting-edge fraud detection algorithm. They assumed speed to market was enough protection—until I framed it differently.

"Your algorithm is like a high-frequency trading strategy. The edge isn’t just in execution but in the logic behind it. If you leave it exposed, competitors can reverse-engineer it, erasing your advantage. IP law acts like an encryption key—protecting your strategy so others can’t replicate or profit from it."

That clicked. Suddenly, protecting their innovation wasn’t just a legal checkbox—it was a competitive necessity.

From Brutalist Buildings to Legal Communication

Growing up in a world of straight lines and concrete, I learned to appreciate functionality. That’s probably why graffiti has always fascinated me.

Graffiti doesn’t fight the structure—it interacts with it. It takes a rigid, unyielding surface and forces it to adjust, to respond to the needs of the people around it. It transforms something fixed into something dynamic.

Analogies work the same way. They take the straight lines of legal reasoning and introduce flexibility, allowing them to fit the world people live in.

That’s why I find them endlessly useful. Just like graffiti makes a city feel alive, analogies make legal guidance feel relevant, intuitive, and human.

The Bottom (Straight) Line (no pun intended)

Analogies aren’t just a tool—they’re a strategy. They align teams, simplify complexity, and turn legal into a force for action.

Where can you use analogies to connect, clarify, and inspire?

My friend and business partner Gabrielle Hartley, Esq recently described me as a charming brutalist. She quickly reassured me—I mean it with the utmost love, because you zero in on what matters. I took it as the highest compliment. If anything, I’m in the process of mastering the shortest distance from A to B—not just in theory, but in practice.

Maybe that’s why I find analogies so powerful. They cut through the noise. They get us to the point, fast. And they remind us that complexity doesn’t have to mean confusion.

So here’s to finding clarity in the structure, meaning in the shadows, and unexpected creativity in the straight lines.

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.