The Match | Team

Word: Team


Sentence:

Team is turning failure into feedback.


Passage:

I started my sophomore year of high school as the varsity starting quarterback. It was the goal I’d worked for, trained for, pictured in my head a thousand times.

We went 0–9.

When that season ended, I made varsity basketball. Another dream. Another chance to prove myself.

We started 0–22.

It wasn’t until the middle of February that I won my first varsity contest. For a 16-year-old who had always found confidence through sports, it was a real test. Not just of skill, but of identity. Losing doesn’t just challenge your performance, it challenges who you think you are.

And more than anything, those two seasons taught me what happens to people when a team isn’t succeeding.

Some teammates quit. Others stayed, but mentally checked out the moment the score turned sour. A few turned on each other, looking for someone to blame. And the hardest part was this: the losses started to feel like our fate. Like the outcome was already written before the game even started.

That’s what losing does when a team doesn’t have a way to stay connected. The mistakes become weapons instead of feedback. Collaboration dries up. Trust evaporates. People stop talking. Or they only talk to criticize.

In those moments, teams don’t just need motivation. They need direction. They need leaders who can keep the group anchored to the goal and to each other, especially when the results aren’t coming.

As I got older, I became one of the leaders on those teams. And the truth is, the losses continued. I never had a winning season as a varsity athlete. But something did change.

My focus shifted from the record to the relationships. From trying to escape the struggle to making sure we didn’t abandon each other inside of it. We didn’t quit. We didn’t splinter. We didn’t turn the locker room into a courtroom.

And I learned something I still believe today: how you lose together matters just as much as how you win together.

A lot of us have been on “losing teams” in adulthood too. Teams that can’t get traction on a project. Teams staring at hard data. Teams stuck in conflict. Teams doing meaningful work but not seeing the outcomes yet.

The only way a team grows is by treating mistakes like information, not embarrassment. Losses don’t have to divide us, they can develop us. But only if we stay connected long enough to learn. The teams that get better aren’t the ones that avoid failure, they’re the ones that face it together and keep adjusting.


Your Turn:

What recent failure on your team needs feedback to help you move forward?


If this sparked something, hit the comment button and share your thoughts. I love hearing your stories, the wins and the hard moments. There’s always something we can learn together.

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2 Comments

  1. Eileen Murphy on January 2, 2026 at 8:40 pm

    Great piece of writing Chad! And great insights. Thank you!

  2. Chad Thomas on January 3, 2026 at 9:44 am

    Thanks Eileen! I know you know the ups and downs of leadership and have always had that energy that see the struggles through hard times as a positive for organizational growth to flourish.

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Chad Thomas

I’m Chad H. Thomas, a former school leader who helped renew one of Chicago’s most challenged high schools. I’m committed to helping others lead with clarity, courage, and care.

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2 Comments

  1. Eileen Murphy on January 2, 2026 at 8:40 pm

    Great piece of writing Chad! And great insights. Thank you!

  2. Chad Thomas on January 3, 2026 at 9:44 am

    Thanks Eileen! I know you know the ups and downs of leadership and have always had that energy that see the struggles through hard times as a positive for organizational growth to flourish.

Leave a Reply Cancel Reply