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What Losing Taught Me About Leadership

#changemanagement #confidence #failforward #highperformance #highperformingteams Oct 28, 2025
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Maybe you’ve been there. The plan was airtight. You had your mission, your North Star, your KPIs, and your team humming like a Formula 1 pit crew. You were ready to crush those quarterly metrics, and then—boom! The project sputtered. The numbers didn’t line up. The ‘sure thing’ campaign didn’t deliver.

Welcome to an uncomfortable—but essential—truth of leadership: sometimes, even your best isn’t enough.

 

From Grand Plans to Gradual Progress

 

As leaders and high performers, we’re taught to set SMART goals, but what happens when you do all that and still fall short? Not all goals are meant to be achieved. Sometimes, they’re meant to stretch us—to expose the gap between where we are and where excellence lives. It’s a tough pill to swallow, especially when your goals are public, the stakes are high, and the timeline is non-negotiable. You’ve declared your mission in bold letters, rallied the team; and then, reality hits: the goal was just a step too far.

 

Life tests us all…

 

Let me confess. This season, my college soccer team lost five games in the final 2 minutes. Five! One game, we were up by two goals with minutes left. Another we were up with seconds left. At first, it felt like some divine prank—the universe was betting against me. (I started checking to make sure I hadn’t broken any mirrors or walked under a ladder.)

 

If you’ve heard me speak, you know that I don’t shy away from inspecting failures. One of my mantra’s for leading change has always been, “What are you here to learn?” Here’s what those losses taught me: we were measuring success by the wrong yardstick.
If your only definition of success is the outcome—winning the championship, hitting the sales quota, closing the merger—you’re setting yourself up for heartache.

 

The Power of Process Goals

 

When the national championship is your only measure, you’ve already built a 99.9% failure rate into your plan. The real key is setting process goals—behaviors and habits within your control that move you closer to your vision.

 

For me as a coach, that meant goals like:

  • More tightly structured and intense practices to hone focus
  • Creating three off-field team events to build cohesion
  • Delivering five pieces of positive feedback per practice to imbue confidence

These goals didn’t depend on luck, referees or weather. They were mine to own.

Leaders in every industry can do the same. Instead of “increase revenue by 25%,” try “conduct 10 client follow-ups weekly” or “mentor two junior staff members this quarter.”

 

When the Bounce Doesn’t Go Your Way

 

In soccer—and in business—the best team doesn’t always win. The bounce goes the wrong way, the market dips, or a global pandemic shows up uninvited. I could see doubt creeping into my team. Resilience isn’t about blind optimism. Sometimes leaders feel this is the moment to avoid addressing issues and ‘Rah Rah’ the team instead to boost morale. High performers know this is a mistake. Resilience is about reflection, recalibration and re-engagement. I examined the data in those losses (watched and re-watched video, reviewed substitution patterns and lineups), and I called a special meeting of the entire team. The meeting was designed to engage the team members in problem-solving. When we analyzed our string of last-minute collapses, we found patterns—poor defensive transitions, miscommunication and fatigue. We didn’t fix it overnight. Our practices leading up to the next match were designed to fix one issue, but we still lost. We fixed another and still lost. We didn’t give up. Like in design thinking, we kept looking past the first early answers. We fixed a third—and finally tied.

 

That first tie was our turning point. It gave us proof we could compete, belief that we belonged, and evidence that perseverance pays off. Our last home game of the season was a tie against the #2 ranked team in the country. This left our team infused with hope and optimism that the best was yet to come. If you ask us – are we a championship team?  My answer would be…Not Yet!

 

The Science of “Not Yet”

 

Psychologist Carol Dweck calls this mindset ‘Not Yet.’ It’s the belief that failure isn’t permanent—it’s simply progress under construction. When you fall short, it’s tempting to double down and try harder, faster and more intensely at the same things. Research shows reflection is what truly fuels improvement.  Harvard’s Francesca Gino found that taking just 15 minutes to reflect on what went wrong improves learning outcomes by as much as 23%. In other words, progress happens when you pause and take a hard look at your actions, assumptions and look for patterns.

 

Finding the Win Inside the Loss

 

This season, my team finished with three wins, seven losses, and two ties—statistically unimpressive. But those ties? They were gold. They marked the beginning of our turnaround. In fact, I have only had one other team with a losing record in my 30-year career.  It was a hard year. Three years later, that group of freshmen went on to win the national championship as seniors.  


Sometimes, the scoreboard lies. The lessons learned in losing seasons—grit, patience, humility and incremental real progress—become the fuel for future greatness.

 

The Leadership Takeaways

When you fall short of your goals:

  1. Separate process from outcome. Measure what’s within your control.
  2. Reflect, don’t react. Ask: What did we learn? What will we keep, and what will we change?
  3. Celebrate progress. Momentum is built on small wins.
  4. Adopt the ‘Not Yet’ mindset. Failure today doesn’t mean forever.

 

Falling short means you’re still climbing. The North Star hasn’t moved. You’re just recalibrating your route. The best teams, leaders and organizations strive for ambitious goals and don’t fear falling short. They fear not learning from it.

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