Why Great Leaders Thrive in Contradiction, Not Certainty

Leaders often face moments where they need to balance long-term vision with short-term needs, be decisive while handling ambiguity, combine logic with emotion, demonstrate confidence with humility, encourage creativity and experimentation with strict guardrails and empower their teams while not losing a sense of control. But how are both possible when one contradicts the other? Aren’t they paradoxical? How can they coexist? The reality is this: leaders can’t always choose between two clear options. They can’t pick sides. They need to hold two seemingly opposing ideas together, lean into the discomfort and create space for competing truths without collapsing into indecision or wasting energy in trying to eliminate the tension instead of learning to live with it. Should prioritizing performance mean that people don’t matter? Should prioritizing performance mean that people don’t matter? Does building at speed imply that reflection is a luxury you can’t afford? Does building at speed imply that reflection is a luxury you can’t afford? If you focus on innovation, should consistency and stability take a backseat? If you focus on innovation, should consistency and stability take a backseat? If you’re empathetic, does it mean you need to stop pushing for high standards and accountability? If you’re empathetic, does it mean you need to stop pushing for high standards and accountability? Leadership isn’t about choosing one side of a tough decision and discarding the other. It’s about learning to live in the tension between seemingly opposite forces and recognizing that both can be true at once. It’s navigating the messy middle—where clarity is limited, tensions are real and trade-offs are inevitable. The most impactful leaders aren’t those who rush to pick sides, but those who can sit with the discomfort of competing demands while still taking clear, confident steps forward. The best leaders are those who learn to live in the tension of paradoxes and find strength in the balance. — Tim Elmore The best leaders are those who learn to live in the tension of paradoxes and find strength in the balance. — Tim Elmore Use these practices to lead through paradox by building a culture where contradictions are not just tolerated, but used as fuel for growth: Let go of either/or, embrace both/and thinking Leaders who lean on either/or thinking believe that in order to move forward, they must choose one path and abandon the other. Binary thinking feels efficient and safe—it provides clarity. And it does work in certain situations—like when you’re dealing with a crisis, choosing both paths isn’t viable due to resource constraints or situations involving a clear right or a wrong answer. Should we comply with this safety regulation? Yes or no. Should we comply with this safety regulation? Yes or no. We have a budget for one project. Should we invest in product A or B? We have a budget for one project. Should we invest in product A or B? Do we report misconduct or stay silent? Do we report misconduct or stay silent? However, making either/or thinking as your default style can be dangerously limiting—you may oversimplify complex problems, create unnecessary trade-offs and shut down possibilities. You may compromise on quality while excessively focusing on speed. Choosing performance at the expense of people comes at the risk of burning them out. Moving fast and breaking things while dismissing structure can lead to inefficiency and chaos. This is where both/and thinking becomes essential. Letting go of the need to choose a single right answer allows you to expand your perspective—you can optimize for speed without ignoring quality, drive outcomes without compromising on well-being and encourage experimentation within safe limits. Both/and thinking is hard. It requires sitting in discomfort to explore better possibilities, not letting the pressure get to you when you’re asked to choose a side or eliminate tension between conflicting priorities. Most of us are taught to pick the right answer—choosing between options A and B—but to practice both/and thinking, you need to resist black-and-white thinking, embrace contradictions and hold multiple perspectives together without rushing to resolve them. To lead through paradox, use both/and thinking over either/or thinking and ask: Who benefits from each side of the tension? How can we include both perspectives? What would a both/and solution look like? Is there a way to honor both priorities, even if they seem to conflict? What are we missing if we only choose one side? How might short-term and long-term goals work together? Where’s the creative possibility that lies between the extremes? Who benefits from each side of the tension? How can we include both perspectives? What would a both/and solution look like? Is there a way to honor both priorities, even if they seem to conflict? What are we missing if we only choose one side? How might short-term and long-term goals work together? Where’s the creative possibility that lies between the extremes? The test of a first‑rate intelligence is the ability to hold two opposing ideas in mind at the same time and still retain the ability to function. — F. Scott Fitzgerald The test of a first‑rate intelligence is the ability to hold two opposing ideas in mind at the same time and still retain the ability to function. — F. Scott Fitzgerald Our brain is wired for simplicity—make a choice, pick a side, solve the problem quickly—because it gives us a sense of control, safety and certainty. But reducing complexity without embracing the discomfort of both/and thinking leads to short-sighted decisions, missed opportunities or addressing wrong problems entirely. Resist the mental shortcut. Don’t settle for easy answers. Think bigger and ask: How can we do both? How can we do both? Cultivate cognitive flexibility Leaders who follow rigid thinking patterns seek definite answers, draw sharp boundaries and cling to outdated strategies that worked in the past, but are no longer relevant. They struggle to pivot as conditions change, become defensive when others challenge assumptions or propose experimenting with new ideas and often make trade-offs that solve today’s problems without addressing future blind spots. Many situations at work can feel ambiguous, uncertain and daunting—rigid thinking serves as an escape route with an illusion of control. Because admitting uncertainty can be equated with incompetence, there’s pressure to appear decisive. There’s comfort in familiarity because navigating the uncharted territory can be risky. The fear of complexity that comes with exploring extreme ideas can also lead to shallow decision-making—simplifying complexity into binary choices, yes or no, right or wrong, good or bad feels more manageable and less scary. But rigid thinking can leave you blindsided, unprepared for change and fall for the trap of oversimplifying problems that need deeper exploration. Leading through paradox demands embracing complexity, not killing it. Instead of narrowing your focus to what’s easy to control or measure, you need to expand your horizon, see the full picture and revel in the joy of making extreme ideas work. You need to build cognitive flexibility. build cognitive flexibility build cognitive flexibility It involves not getting locked into a single point of view, exploring multiple truths, inviting diverse inputs and adapting strategies as new information emerges—zooming in for detail and zooming out for perspective, listening to competing needs, weighing trade-offs, testing different approaches, learning from feedback and pivoting when condition shifts. Cognitive flexibility—the ability to shift between different perspectives, adapt your thinking and holding competing ideas without getting stuck in rigid patterns—can keep you mentally agile in the face of uncertainty, complexity and change. To become a flexible thinker, ask: What assumptions am I holding on to? How might someone else view this problem? Is there another option I haven’t considered? What would make me change my mind? What assumptions am I holding on to? How might someone else view this problem? Is there another option I haven’t considered? What would make me change my mind? Integrative thinking is the ability to face constructively the tension of opposing ideas and, instead of choosing one at the expense of the other, generate a creative resolution of the tension in the form of a new idea that contains elements of the opposing ideas but is superior to each. — Roger Martin Integrative thinking is the ability to face constructively the tension of opposing ideas and, instead of choosing one at the expense of the other, generate a creative resolution of the tension in the form of a new idea that contains elements of the opposing ideas but is superior to each. — Roger Martin The more flexible your mind, the stronger will be your leadership presence. Lead with curiosity, not control. Stop defaulting to fixed assumptions or clinging to past successes. Be transparent about trade-offs Trade-offs are an inevitable part of decision-making. You can’t satisfy all needs. You can’t optimize everything at once. You can’t offer complete autonomy while also trying to maintain a sense of control. You can’t promote innovation at the cost of business as usual. You can’t tell people to build fast without paying attention to its impact on quality. When leaders aren’t transparent about trade-offs involved in a decision, it leads to confusion, disappointment and distrust. People feel blindsided as they’re left guessing why a certain path was chosen. They may nod without feeling invested in the decision. Feelings of resentment can also creep in because the thing they valued was being sacrificed without understanding why something else holds more value. These mismatches in expectations can lower morale and prevent them from putting their best efforts at work. Worrying that sharing compromises behind a decision will make them look weak or unsure can make leaders omit trade-offs and paint a rosy picture. Fear of disappointing stakeholders or the discomfort of dealing with a conflict can also make them spin truth instead of communicating reality. The belief that trade-offs are messy details that people shouldn’t be bothered with creates another barrier to transparency, making leaders communicate a false narrative or half-truth. Making trade-offs visible to the team is a strategic act—it builds trust. When leaders trust their teams with the whole picture, they do more than just explain decisions—they equip them to navigate decisions with clarity and maturity. It signals honesty and respect for their ability to handle complexity. It also ensures everyone operates from the same understanding without making faulty assumptions or wasting time in dealing with conflicting expectations or misunderstandings. Even when people don’t agree with the decision or love the choice, the simple act of making them understand the “why” behind the “what” can lead to stronger commitment and more thoughtful execution. “why” “what” To communicate trade-offs effectively, say: We’ve listened to all the concerns, and the reality is … We know this decision won’t satisfy everyone equally. But we want you to understand … Right now, we’re leaning more toward consistency, even if it slows innovation temporarily. We’re open to feedback on how this plays out. If you see unintended consequences, speak up. We’re doing X now so we can do Y better later. We’ve listened to all the concerns, and the reality is … We know this decision won’t satisfy everyone equally. But we want you to understand … Right now, we’re leaning more toward consistency, even if it slows innovation temporarily. We’re open to feedback on how this plays out. If you see unintended consequences, speak up. We’re doing X now so we can do Y better later. Trade-offs are not something to be ignored or decried. They are something to be embraced and made deliberately, strategically, and thoughtfully. — Greg McKeown Trade-offs are not something to be ignored or decried. They are something to be embraced and made deliberately, strategically, and thoughtfully. — Greg McKeown Choices at work are rarely isolated—pursuing one goal often impacts another. Reduce friction by clearly articulating the trade-offs so that team members can focus energy on progress, not second-guessing decisions. Design safe zones for experimentation Leaders who punish failure or demand perfection stifle experimentation by creating a culture of fear. People worry about being called out, scolded or punished for making mistakes, not living up to expectations or failing to deliver results. Instead of taking risks, they learn to play it safe. They don’t challenge the norm or try anything that might not work. Instead of taking initiatives, testing new ideas and exploring possibilities, they stick to what’s worked in the past even if it’s no longer effective. They think every experiment puts their reputation at stake. They worry about being blamed for their mistakes. Unknowns, uncertainty and obstacles are treated as threats instead of learning opportunities. Without the agility to navigate complexity, people lean towards one right answer instead of building the capacity to live, test and grow in the space between contradictions. They become disinterested, inattentive and disengaged instead of showing up with curiosity. being blamed being blamed Encouraging risk-taking, running tests or piloting ideas is not boundaryless freedom—doing things without a clear scope or agenda, being careless by making mistakes that could have been easily avoided or wasting time and energy on things that don’t align with long-term goals. It requires defining the scope, timeframe and criteria for experimentation, putting guardrails to keep risk in check, modeling openness to being wrong and building reflection loops to apply useful insights and make progress on goals. Leaders who purposefully design safe zones for experimentation not only increase their team’s ability to innovate and succeed, they equip them to navigate the tension of opposing demands by making it safe to explore, learn and evolve without fear of failure. To unlock innovation when handling paradoxes: Normalize failure as a byproduct of trying new things. Make clear the difference between reckless behavior and thoughtful risk-taking. Promote a culture of test and learn, rather than plan and perfect. Encourage curiosity and questioning, not always appearing certain. Create a feedback culture where people seek input early and often. Normalize failure as a byproduct of trying new things. Make clear the difference between reckless behavior and thoughtful risk-taking. Promote a culture of test and learn, rather than plan and perfect. Encourage curiosity and questioning, not always appearing certain. Create a feedback culture where people seek input early and often. Creating safety is not about being nice … but rather about creating a culture of openness where teammates can share learnings, be direct, take risks, admit they ‘screwed up,’ and are willing to ask for help. — Stefano Mastrogiacomo Creating safety is not about being nice … but rather about creating a culture of openness where teammates can share learnings, be direct, take risks, admit they ‘screwed up,’ and are willing to ask for help. — Stefano Mastrogiacomo Experimentation shows people that failure and progress can coexist. This makes them think bold while still operating within certain constraints and limits. Safe zones don’t stifle innovation—they’re strategic. Invite constructive tension Leaders who steer conversations away from conflict, prioritize harmony over debate and intervene to smooth things over when team members disagree, voice differences of opinion or challenge assumptions, send the message that raising uncomfortable truths may lead to friction rather than progress. In trying to protect team morale, they end up suppressing their energy to lean into discomfort and rise above the challenge. Over time, people stop voicing concerns. They nod along in meetings, but privately disengage. Diplomacy takes priority over honesty, consensus over clarity and safety over bold decisions. When leaders avoid tension, teams learn to avoid it too. They make decisions that are comfortable in the short-term, even though it leads to long-term stagnation. High performers disengage, sensing that challenge and complexity are unwelcome. This silent erosion doesn’t happen overnight. It slowly builds with every act of avoidance that shows up at work. Learning to not only hold constructive tension, but invite it consciously is the only way to show teams that friction is not a dysfunction, it’s fuel for forward motion—contradictions can challenge us, stretch us and make us explore paths that we would be otherwise unwilling to take. Encouraging teams to stay curious rather than reactive when opinions clash, setting ground rules for constructive disagreements and allowing them to sit with tension instead of rushing to resolve it builds a culture of psychological safety and shared accountability. It teaches people that discomfort is not a signal to retreat, but an invitation to listen more openly, engage more thoughtfully, deepen understanding and arrive at breakthrough solutions that wouldn’t emerge in the absence of constructive tension. Invite constructive tension by asking: What’s another way to look at this? What tensions are we holding right now? Can both of these things be true at the same time? What are we not saying that needs to be said? What’s the strongest argument against our current thinking? What might we be avoiding because it’s uncomfortable? What assumptions are we making here? What’s the cost of not having this conversation? What’s another way to look at this? What tensions are we holding right now? Can both of these things be true at the same time? What are we not saying that needs to be said? What’s the strongest argument against our current thinking? What might we be avoiding because it’s uncomfortable? What assumptions are we making here? What’s the cost of not having this conversation? Decision making improves if you can stimulate constructive conflict, or vigorous debate, within teams. — Michael Roberto Decision making improves if you can stimulate constructive conflict, or vigorous debate, within teams. — Michael Roberto Constructive tension is not something to be feared—it’s a catalyst for clarity, creativity and progress. Create space for deeper dialogue and better decisions by inviting discomfort and resisting the urge to smooth things over quickly. Summary Paradox lives in the grey, but that’s where the magic happens. Instead of forcing false choices, great leaders ask, “What if both can be true?” This mindset doesn’t simplify complexity—it works with it, unlocking solutions that don’t require sacrificing one value for another. In a world where today’s answer might not work tomorrow, rigid thinking is a liability. Leaders who stay mentally agile—able to zoom in and out, shift perspective and hold opposing truths—are the ones who thrive in paradox. Flexibility isn’t weakness—it’s wisdom in motion. Let’s be honest: we can’t have it all. But when leaders name what’s being prioritized and what’s not, they earn trust. Transparency doesn’t make tough calls easier, but it brings people into the process and signals that decisions are made with thought, not ego. Paradox demands that we move before we’re fully ready and that means creating space to experiment. When teams know they can test ideas without fear of failure, they stop playing safe and start getting bold. Safe zones aren’t soft, they’re launchpads for learning and growth. Tension isn’t the problem. Silence is. Leaders who welcome healthy friction unlock deeper thinking, sharper insight and more resilient teams. The goal isn’t to avoid conflict—it’s to make space for people to do their best work by challenging assumptions and revealing better paths forward. Paradox lives in the grey, but that’s where the magic happens. Instead of forcing false choices, great leaders ask, “What if both can be true?” This mindset doesn’t simplify complexity—it works with it, unlocking solutions that don’t require sacrificing one value for another. Paradox lives in the grey, but that’s where the magic happens. Instead of forcing false choices, great leaders ask, “What if both can be true?” This mindset doesn’t simplify complexity—it works with it, unlocking solutions that don’t require sacrificing one value for another. In a world where today’s answer might not work tomorrow, rigid thinking is a liability. Leaders who stay mentally agile—able to zoom in and out, shift perspective and hold opposing truths—are the ones who thrive in paradox. Flexibility isn’t weakness—it’s wisdom in motion. In a world where today’s answer might not work tomorrow, rigid thinking is a liability. Leaders who stay mentally agile—able to zoom in and out, shift perspective and hold opposing truths—are the ones who thrive in paradox. Flexibility isn’t weakness—it’s wisdom in motion. Let’s be honest: we can’t have it all. But when leaders name what’s being prioritized and what’s not, they earn trust. Transparency doesn’t make tough calls easier, but it brings people into the process and signals that decisions are made with thought, not ego. Let’s be honest: we can’t have it all. But when leaders name what’s being prioritized and what’s not, they earn trust. Transparency doesn’t make tough calls easier, but it brings people into the process and signals that decisions are made with thought, not ego. Paradox demands that we move before we’re fully ready and that means creating space to experiment. When teams know they can test ideas without fear of failure, they stop playing safe and start getting bold. Safe zones aren’t soft, they’re launchpads for learning and growth. Paradox demands that we move before we’re fully ready and that means creating space to experiment. When teams know they can test ideas without fear of failure, they stop playing safe and start getting bold. Safe zones aren’t soft, they’re launchpads for learning and growth. Tension isn’t the problem. Silence is. Leaders who welcome healthy friction unlock deeper thinking, sharper insight and more resilient teams. The goal isn’t to avoid conflict—it’s to make space for people to do their best work by challenging assumptions and revealing better paths forward. Tension isn’t the problem. Silence is. Leaders who welcome healthy friction unlock deeper thinking, sharper insight and more resilient teams. The goal isn’t to avoid conflict—it’s to make space for people to do their best work by challenging assumptions and revealing better paths forward.