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The Heart of the Matter

Do you know how to recognize wisdom?


Pay attention to who people seek out when problems get complicated. They're probably the wisest in the room.

Nate stood apart from the credentialed experts at the executive search firm where I worked.

We'd been brought in to diagnose why a client's hiring operation wasn’t working and to offer solutions. While the traditional consultants analyzed the client’s processes, Nate analyzed their people. He spent extra time with them, asking unexpected questions and noting the differences between the criteria they expressed and what they actually rewarded. It wasn’t always clear what he was hunting for, but then he’d show up to meetings with poignant, human assessments that made sense of the client’s struggles.

When it was time to finalize our recommendations, the older consultants pitched interview scoring systems and personality tests that we’d used for previous projects. Nate suggested having finalists work through an actual problem alongside the team they'd be joining, just to see who people naturally turned to. When we tried it, the client’s team picked someone nobody in management had ranked first, and they were the perfect fit.

Watching him, I recognized a quality that transcended experience. Nate possessed wisdom: the confidence to trust he'd figure things out, the courage to defend unconventional solutions, and the curiosity to question what everyone else accepted. He could see patterns others missed because he was looking in unique places.

Wisdom comes naturally to some, but most people need to cultivate it deliberately.

What wisdom is

People confuse wisdom with all sorts of things: age, experience, how much someone reads. It's none of those. To understand what it actually is, you have to see how it builds from simpler elements.

Information is everywhere: raw data, facts, images. It's instantly available but meaningless until you do something with it. Knowledge develops through applying that information, trying things repeatedly, and seeing what works and what doesn't. You learn by doing.

Wisdom comes from holding two truths at once: deep self-awareness and radical humility about what you don't know. Your experiences form a lens through which you process everything, shaping your values and beliefs, leaving inevitable blind spots. Wise people get this. They hunt for perspectives that challenge their own, knowing that's where they’ll find greater truth.

Wisdom often comes from struggle because failure forces you to examine your assumptions. Each difficult experience, if you stay open to it, expands what you're capable of understanding.

Which means professional development is backwards. Credentials and titles are said to make you wise, but they won't. You become wise by solving problems without the right instructions and by seeking out people who think you're wrong.

Why organizations lose it

Companies gravitate toward what they can measure, like short-term results and familiar expertise. Those metrics can’t capture the judgment and mentorship skills that actually signal wisdom.

Workplaces reflect this failure. Too many managers lack the tools to lead. People move into roles they aren't prepared for. Employees feel isolated, unsure how their work connects to the whole. The systems that tolerate poor behavior also block the conditions where wisdom could circulate.

Yet wisdom becomes most powerful when it's shared. A wise leader notices what others overlook and draws attention to it in ways that change the course of events. Now imagine a whole team operating that way, each person contributing their own particular understanding. Problems would be caught before they worsened. The organization would develop a collective intelligence that no individual could achieve alone.

This only works when wisdom flows between people. When leaders hoard knowledge instead of sharing it or protect their expertise instead of developing others, wisdom gets trapped in silos. Without that flow, you get exactly what we have now: disconnection, disengagement, and expensive mistakes on repeat.

Here's what you can do differently.

Consider multiple realities.

We all see through our own lens. Before having a hard conversation, imagine three ways the other person might be experiencing the situation. Maybe they're protecting their credibility, maybe they're under pressure you can't see, maybe they're managing relationships you don't know about. By working to understand their reality, you turn a confrontation into a collaboration.

Transfer knowledge between generations.

Wisdom isn't top-down. Young workers catch patterns their leaders stopped noticing. Senior professionals carry institutional knowledge that no database can capture. Find someone ten years different from you. Meet them without phones, take walks together. Fill in the gaps: "What do you see that I don't?" Inspire each other.

Admit what you don't know.

Saying "I don't know yet, but here's how we'll figure it out," builds trust and shows others how to face uncertainty. When people see you pairing honesty with action, they learn to do the same. Your transparency becomes collective strength.

Stop compartmentalizing your instincts.

You’re not one person at home and another at work. When you hit a workplace conflict, ask: "How would I handle this if it were a family situation?" Wisdom moves with you across domains. Notice the lessons that travel, and let them sharpen your leadership in every space.

You're wise. Own it.

If you’ve read this far, you already have the spark that wisdom depends on. You’re curious! It’s uncomfortable to interrogate the world around you, but you’re one of the few willing to keep digging.

So, how will you harness this? What assumptions will you challenge, what actions will you take that create change?

Organizations that thrive in the coming years will be those that nurture creative, wise talent and people who are confident enough to act, fierce defenders of what matters to them, and curious to keep asking.

Lead the way.

Sending love and light,

Ginny

1440 W. Taylor St #1055, Chicago, IL 60607
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