Checkers and Leadership

Here’s a first-time-ever moment worth capturing: my wife and I get to take our twin 7-year-old

granddaughters to school once a week. Recently, after breakfast, they asked to play checkers. Now, here’s the twist—they had never played checkers before.

So, my wife Kris explained the rules. One of the most important things she told them was this: “You’re each going to lose checkers. That’s part of the game. We don’t want to see you get mad when it happens—it’s just how the game works.”

I admired how she framed it. From the beginning, they were reminded: losing pieces isn’t failure; it’s part of the journey.

Kris helped one granddaughter, and I helped the other. Now, between the two of us, I’ll admit I’m the more competitive one. Deep down, I was thinking, we should win this game (lol). But the truth was obvious: it wasn’t about winning—it was about learning to play.

“I Can’t Do Anything!”

Partway through the game, the granddaughter I was helping sighed in frustration. “I can’t DO anything!”

She stared at the board as if she were trapped, stuck with no options.

So I asked gently, “Which ones can you move?”

She paused, studied the board, and then pointed to three different checkers. We walked through each option together, talking about what might happen with each move. After some thought, I encouraged her, “Pick the one you want to try.”

It struck me in that moment: she didn’t need to know the perfect move. She just needed to choose one and learn from it. Isn’t that leadership in a nutshell?

The Myth of the Perfect Move

In both checkers and leadership, we often get caught up in the idea of making the best decision. We analyze, we predict, we try to calculate every possible outcome. But the truth is—we never know exactly what will happen.

Her sister might counter with an unexpected move. A new opportunity or obstacle could pop up. The future is not only unpredictable—it’s filled with endless possibilities.

When we get stuck searching for the perfect move, we risk making no move at all. Analysis paralysis creeps in. Fear of choosing wrong paralyzes us. And in leadership, hesitation can cost us momentum, trust, and opportunities.

Decisions as Stepping Stones

Leadership isn’t about predicting every possibility—it’s about moving forward with the best decision you can make in the moment.

Just like in checkers, each move you make opens up a new board. A new set of options. A new set of challenges. The game evolves as you go. The key is not perfection, but progression. Each choice is a stepping stone. What matters most is that you keep moving, keep learning, and keep adjusting along the way. That’s why I reminded my granddaughter: “Pick the one you want to try.” She chose, she played, and the game went on.

Lessons for Leaders

That moment at the checkerboard offers a few lessons worth carrying into leadership:

1. Expect Losses Along the Way Just like Kris reminded the girls they’d lose pieces, leaders need to remember—losses are part of the journey. You can’t lead without sacrifice, setbacks, or mistakes. Don’t fear them; embrace them as part of growth.

2. Name Your Options Clearly When you feel stuck, take time to identify the real options in front of you. My granddaughter thought she had no moves—until she slowed down and saw three. Leaders often have more choices than they initially believe.

3. Choose Progress Over Perfection Don’t freeze trying to predict the “perfect” outcome. Make the wisest decision you can in the moment and move forward. Each choice creates new opportunities to learn.

4. Coach, Don’t Control I didn’t play the checker for her. I simply asked questions, offered perspective, and let her choose. That’s leadership: guiding others to think and act for themselves.

A Game Worth Playing

At the end of the morning, nobody remembered who won. What mattered was that they learned to play, took risks, and discovered how to keep moving forward. Leadership is a lot like that. It’s not about winning every move. It’s about playing the game with wisdom, courage, and resilience.

So the next time you feel stuck, staring at the board of your own life or leadership, remember this:

You don’t need the perfect move. You just need the next move. Pick it. Try it. Learn from it. Then keep going.

Because leadership, like checkers, is a game worth playing.

Brian