Introduction: Two Mindsets That Define Leaders

In sports, we’ve all seen it happen.
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A team dominates the first half, then barely escapes with a win.
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What changed?
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In the first half, they played to win.

In the second, they played not to lose.

It’s the same in leadership.
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Too many leaders start with vision, energy, and bold moves and then shift into protection mode. They stop taking risks. They focus on not making mistakes instead of creating momentum.
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It feels safe. But “safe” leadership has a hidden cost: disengaged teams, missed opportunities, and cultures that drift into mediocrity.
Here’s how to recognize if you’re leading not to lose and what it takes to flip the switch back to playing to win.

The Difference Between Playing to Win and Playing Not to Lose

Playing to Win:

• Bold, proactive decisions
• Willingness to take calculated risks
• Inspires teams with vision
• Focused on long-term growth

Playing Not to Lose:

• Defensive decision-making
• Avoids risk at all costs
• Prioritizes avoiding mistakes over making impact
• Focused on maintaining the status quo

Leaders who play not to lose don’t notice the shift right away. But their teams do. The energy changes. Innovation stalls. People stop stretching themselves because they see their leader isn’t stretching either.

Story From the Stage: The Scoreboard Shift

I often share this with audiences:
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Imagine watching your favorite football team.
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At halftime, they’re up 30–0.
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By the final two minutes, the score is 30–28.
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What happened?
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In the first half, they came out aggressive, playing to win.
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In the second, they got cautious, playing not to lose.
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That’s the same trap leaders fall into. The scoreboard looks good, so they stop pressing forward. Instead, they protect. They play defense.
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But business is never won by playing defense alone.

The Cost of Safe Leadership

Playing not to lose feels comfortable in the short term. But the costs compound:
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1. Missed Opportunities: Markets shift. Customers evolve. Playing it safe means competitors who take risks get ahead.

2. Lower Engagement: Employees see when leaders stop stretching. And people rarely bring their best to a team that’s coasting.

3. Culture of Fear: If leadership is focused on “not messing up,” people start hiding mistakes and avoiding new ideas.

4. Loss of Trust: Teams don’t trust leaders who settle. They want leaders who believe the best is still ahead.

How to Shift Back to Playing to Win

The good news? Leaders can reset fast. Here are 5 ways to get back to playing to win:
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1. Revisit Your “Day One” Energy
Remember how you showed up the day you got the role? Hungry, curious, determined? Recommit to that posture, and your team will follow.
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2. Take Calculated Risks
Stop waiting for 100% certainty before making decisions. Playing to win means moving with 70% clarity and learning along the way.
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3. Celebrate Bold Attempts
Reward effort, not just results. When people take smart risks, even if they don’t fully land, make it clear you value courage.
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4. Shorten the Timeline
Try 30-day challenges with your team. Urgency forces action and creates momentum.
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5. Model It Out Loud
Leaders set the tone. If you’re defensive, your people will be too. If you’re bold, they’ll rise with you.

The Sports Lesson for Business Leaders

Athletes know momentum is fragile. Lose your edge, and the game slips away.
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Leaders face the same reality. The scoreboard today doesn’t guarantee tomorrow’s win.
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That’s why the best leaders stay aggressive. They play to win — not just in the first half, but all the way through.

FAQs

‍Q: What does “playing to win” mean in leadership?
A: It means leading proactively, taking calculated risks, and inspiring teams with vision — instead of settling for maintaining the status quo.

Q: Why do leaders play not to lose?
A: Comfort, fear of failure, or past success can push leaders into a defensive mindset. It feels safer short-term, but it slowly erodes culture and performance.
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Q: How do I know if I’m leading too “safe”?
A: If you’re avoiding risk, saying “no” more than “yes,” and rarely stretching your team, you may be in defensive mode.
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Q: How can leaders shift back to bold leadership?
A: Recommit to Day One behaviors, reward bold attempts, shorten timeframes, and model courage in your own decisions.

Final Word

Leadership is not about protecting what you have. it’s about creating what’s next.
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The question every leader must ask is simple:
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Am I playing to win, or just trying not to lose?

Your team knows the answer already. The good news is, you can choose to reset  today.