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What Valentine’s Day and Presidents’ Day Teach Us About Courage and Care
February gives us a gift most months don’t: two holidays that seem unrelated but, in truth, belong in the same leadership conversation. On one side, we have Valentine’s Day—roses, chocolate, and grand gestures of affection. On the other, Presidents’ Day—a nod to power, responsibility, and the weight of decision-making. One celebrates the heart. The other honors backbone. But here’s the truth: great leadership requires both. Backbone without heart creates fear. Heart without backbone creates chaos. Together, they create trust. Let me tell you a story. A CEO I once worked with—let’s call her Maria—prided herself on being “nice.” Her team loved her. They described her as kind, approachable, and supportive. But performance was slipping. Deadlines were missed. Accountability was fuzzy. Quality was inconsistent. Maria avoided tough conversations because she didn’t want to hurt feelings. A nothing leader—David—ran a tight ship. Metrics were clear. Expectations were sharp. Underperformance was addressed swiftly. But turnover was rising. His team complied, but they did not commit. David had backbone without heart. Maria had heart without backbone. Neither had the kind of leadership that builds enduring or high-performing organizations. The leaders we remember—whether in business or in the Oval Office—are those who manage to hold both. Think of Abraham Lincoln. He made excruciating decisions during the Civil War, yet he was known for empathy and humility. Or George Washington, who relinquished power voluntarily—a profound act of disciplined restraint and moral courage. More recently, Barack Obama often spoke about leading with both toughness and compassion, especially in times of national division. Whether or not we agree with every policy decision, history tends to remember leaders who paired conviction with care. In organizations, the same principle applies. So what does it actually look like to lead with backbone and heart? Let’s make it practical. 1. Tell the Truth Kindly (Backbone + Heart in Conversations) Courage in leadership often shows up in one moment: the difficult conversation. Backbone says: “This isn’t working.” Heart says: “I believe in you.” When delivering feedback:
Candor without care feels like attack. Care without candor feels like avoidance. Your job is both. 2. Set Boundaries That Protect the Team Heart-led leaders sometimes overextend themselves—and their teams. They say yes too often. They shield underperformance. They carry too much. Backbone asks: “What standard are we committed to?” Heart asks: “What is sustainable for our people?” Try this:
Boundaries are not harsh. They are clarifying. They are kind. Teams feel safer when expectations are clear. 3. Make Decisions You Can Sleep With Presidents’ Day reminds us that leadership sometimes requires unpopular decisions. Layoffs. Budget cuts. Strategic pivots. Leading with backbone means you don’t hide from hard calls. Leading with heart means you don’t make them casually. Before a significant decision, ask yourself:
You may still have to disappoint someone. But when people sense integrity, they are more likely to stay engaged—even in disagreement. 4. Recognize and Reward with Intention Valentine’s Day is about expressing appreciation. In leadership, appreciation is not a luxury—it’s fuel. Backbone sets expectations. Heart reinforces effort and progress. Three simple practices:
People do not burn out from hard work alone. They burn out from work that feels unseen or meaningless. 5. Model Emotional Regulation In times of stress, teams scan their leader’s face before they read the memo. Backbone does not mean emotional volatility. Heart does not mean emotional leakage. Emotional maturity looks like:
When you regulate yourself, you stabilize the room. 6. Choose Courage Over Comfort This may be the simplest test of backbone and heart: are you choosing courage or comfort? Comfort says:
Heart ensures that courage does not become cruelty. Backbone ensures that compassion does not become complacency. A Leadership Reflection for February As you move through this month, consider two questions:
Most leaders tilt naturally in one direction. The work is in strengthening the other muscle. Leadership is not about being liked. Nor is it about being feared. It is about being trusted. Trust grows when people know two things:
That is the blend of Valentine’s Day and Presidents’ Day leadership. Courage and care. Conviction and compassion. Backbone and heart. The leaders who master both do more than manage results—they build cultures worth staying in. And as I often remind leaders: “the workplace doesn’t need more managers. It needs leader-managers who can stand firm without losing their humanity.” This February, may we all lead with both!
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AuthorLynda Silsbee is Founder and President of the Alliance for Leadership Acceleration. She has spent more than 30 years creating and leading high performance teams. Along with the other LEAP Certified Coaches, she reports that helping managers make the LEAP to leader is one of the most fulfilling aspects of her work. Archives
February 2026
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