Leading Through Paradox

There are days in leadership when it doesn’t matter how much planning, foresight, or proactive strategy you put in, you still end up staring at a situation where every option carries a cost.

You’ve done the work. You’ve anticipated the hurdles, built relationships, stayed ahead of the curve, and made thoughtful, values-based decisions. And still, you find yourself backed into a corner where no matter which path you take, someone’s going to be disappointed, a program might suffer, or a relationship could fracture.

Every leader who’s been in the seat long enough knows what this feels like.

What separates the good from the remarkable isn’t the ability to avoid these moments (because you can’t), but the ability to look deeper inside them. The truly grounded leaders, the ones who stay centered when the pressure turns up, are able to dig into a complex, costly situation and still find something worth carrying forward.

This isn’t about “learning from mistakes.” It’s about finding a long-term win inside the tension. It's extracting a nugget of value, integrity, or direction that sets your team or organization up for something stronger down the road.

The Reality of the Paradox

The truth is, even great foresight fails sometimes. The world we lead in is complex, political, emotional, and unpredictable. Sometimes the perfect plan still ends with you choosing between two options that both hurt.

And that’s okay. Because leadership isn’t about always choosing the right path. It’s about choosing the most honest path and walking it with courage.

How to Find the Win in the Paradox

Over the years, and through a few of my own “every-option-costs-something” moments, I’ve found a few ways to navigate these spots without losing your footing:

1. Reframe the problem.

Paradoxical situations usually look binary: this or that, right or wrong, win or lose. The first step is to zoom out. Ask yourself:

Is this truly an either/or situation, or am I missing a third path?

What’s the real problem I’m trying to solve?

Am I focused on the short-term noise instead of the long-term signal?

Sometimes the “win” isn’t in this week or even this year, it’s in setting up the organization to win three years from now.

2. Own the tension.

When things get messy, it’s tempting to soften the edges or talk around the truth. But people respect candor. Be upfront about what’s tough, what’s broken, and what’s simply unavoidable.

Transparency in these moments doesn’t make you weak, it makes you trustworthy.

3. Collaborate and widen the circle.

No one person sees the full picture. Pull others in. Listen broadly. Often the best ideas to navigate a paradox come from people one layer removed from the chaos. Collaboration brings clarity, and sometimes, creativity you didn’t see coming.

4. Lean into your values.

When the scoreboard doesn’t look good, your integrity is the win. There are moments when you won’t please everyone, but you can still act in alignment with who you are and what you stand for. That’s how culture is built and protected.

5. Move forward, even if it’s small.

Waiting for perfect information or universal agreement is usually how organizations get stuck. Make a small, bold move. Something visible that restores momentum. Even incremental progress is progress. Momentum often creates clarity that planning alone can’t.

6. Extract the nugget.

After the dust settles, pause. What’s the piece of value hidden inside the tension? Maybe it’s a relationship that deepened under pressure, a system you’ll never overlook again, or a sharper understanding of how your team responds when things get hard.

Capture it. Name it. Build on it. That’s your long-game win.

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Winston Churchill said it best:

“Success is not final, failure is not fatal: it is the courage to continue that counts.”

And maybe that’s the heartbeat of this whole topic. The courage to continue.