Paradox-aware leaders are rare. Are you one of them?
Nov 11, 2025
Compromise, as it’s commonly understood, isn’t useful in politics or parking negotiations. Split-the-difference compromises rarely last because they fail to address the real priorities of either side. Lasting solutions don’t give everyone half of what they want—they fully address the fundamental important things each side is fighting for.
Paradox-aware leaders understand this. They don’t water down competing goods into a lukewarm middle. They practice Both/And—holding two necessary truths at once, even when they appear to contradict. That’s not indecision; it’s mastery of complexity.
Start Beneath the Either/Or
When confronted with a hard binary—Do I keep working with a problem employee or let them go?—paradox-aware leaders don’t settle for either obvious option. They look beneath the surface of the question and ask, What good am I trying to achieve with either option?
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Am I trying to improve team performance and business outcomes?
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Am I trying to repair unhealthy relationship patterns?
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Am I trying to set a pattern of accountability for the team?
They do the same with other dilemmas: Do I cut spending or make a bold strategic investment? Rather than choosing one or the other, they ask what both options are ultimately trying to achieve.
Paradox-aware leaders search for the most important goal—the one that, if met, makes every other goal easier to reach. They identify the crux barrier—the single obstacle that, once solved, unlocks the rest. From there, they design solutions that honor multiple necessary goods: clarity and compassion, prudence and progress, patience and momentum.
Why Both/And Isn’t A Mushy Middle
Only the obvious solutions are truly contradictory. The two sides of a paradox, by contrast, are actually mutually dependent. Truth-telling without tact damages trust; tact without truth corrodes integrity. Speed without strategy wastes effort; strategy without speed misses opportunity.
Paradox-aware leaders learn to uncover the principles beneath the either/or and build solutions that express both. That work often begins with self-awareness—seeing the hidden commitments that keep them stuck. Once they recognize how their own choices shape their circumstances, they stop waiting for conditions to change and start experimenting toward better outcomes.
The most creative, durable solutions live in the tension between necessary things that appear to conflict. Paradox-aware leaders are comfortable living there.
Two everyday paradoxes to notice this week
Frankness vs. Diplomacy
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Do you take care to protect others’ dignity when you speak?
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Do you share honest feedback, even when it’s uncomfortable?
Patience vs. Urgency
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Do you allow time for personal growth and thoughtful decisions?
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Do you make sure things get done without delay?
Each of these tendencies is a choice. If your outcomes aren’t what you want, the good news is simple: you can choose differently.
Practicing paradox in real decisions
Try this five-step loop the next time you face an either/or:
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Clarify the core goal. Which outcome would make everything else easier?
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Find the crux barrier. What single obstacle, if solved, would unlock the rest?
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Name the necessary goods. What two principles matter most here?
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Design Both/And experiments. What small tests honor both necessary goods?
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Measure and adjust. Keep what works, refine what doesn’t, and keep learning.
A closing nudge—and an invitation
Paradox-aware leadership is rare, but it’s a superpower worth spreading. On Tuesday, November 18 at 9:00 a.m. Pacific / 12:00 p.m. Eastern, I’ll be officially releasing my new book: Tension—Mastering the Superpower of Paradox-Aware Leadership.
For the first few hours, the Kindle edition will be just $0.99. Whether you read on Kindle or not, your early purchase will help lift the profile of paradox-aware leadership so more teams can benefit.
Mark your calendar for Tuesday, November 18 at 9 a.m. PT / Noon ET. Join the waitlist if you'd like a reminder with a link for the promotional price.
See your own paradox-awareness in seven minutes
If you’d like a quick snapshot of where you stand, take the Leadership Strengths Self Assessment. It’s a fast, insightful way to see your natural leanings and identify where a Both/And mindset could transform your impact.
What if your greatest strength is also holding you back?
Take the free Leadership Strengths Self-Assessment and start a conversation with your team about how polarized leadership strengths can limit your results.
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