Is Your Organization Playing Chess or Checkers?

Is complexity leaving your organization behind?

That’s a question we considered at a workshop I attended recently. Author Mark Miller and a team of facilitators walked a large group through the content of his new book Chess Not Checkers. The boardgame imagery? It’s symbolic for what happens as organizations grow. In the early stages of most small organizations or teams, the rules are simplistic and team members may play interchangeable roles much like the game pieces in a checkers game. But as growth occurs, complexity kicks in. Roles require specialists to address additional complications. The playing field starts to resemble a game of chess, rather than checkers. If we’re not careful, we’ll fall behind.


That’s what the workshop addressed. How do leaders elevate their game to match new organizational complexities? You can find the answers in the book (as well as the digital field guide), but let me share the four big ideas we discussed.

Bet on Leadership

It shouldn’t be a surprise that organizational success starts with leadership. But many organization are extremely reactive in this respect. They place their bet too late by waiting until new leaders are needed to begin looking for them. The best organizations have a strong leadership bench. They know who their future leaders are and work hard to prepare them beforehand so they are ready to go when the call comes.

The other thing to note is that a bet is not a sure thing. Not every leader works out. But in Mark Miller’s words, “You cannot be a great organization without great leadership.” Why? Because leadership growth always precedes organizational growth.

Act as One

It’s one thing for a leadership team to be on the same page. But what about the rest of the organization? It’s true that leadership teams are uniquely responsible for creating clarity. That is one job that cannot be outsourced. But do key organizational messages cascade effectively throughout the organization or quickly go awry like a kid’s game of telephone? Or worse yet, do they even leave the boardroom?

The silver lining in this regard is that nearly every organization struggles with communication at least to some extent. Perhaps it’s just part of the human condition. But great leaders make the extra effort to ensure key messages get to every level using multiple communication methods. And by the way, it’s impossible to over-communicate what’s truly important (in case you were worried about that).

Win the Heart

Great organizations foster a spirit of shared ownership. Instead of working for “the man,” followers and employees show up to work for themselves. It’s a completely different mentality, but it’s starts with leadership.

Has your organization ever helped your followers’ dreams come true? I’m not just talking about their need to make rent that month. Actual dreams. This was a real question posed at the workshop. Everyone present wrote down a life dream and shared it with the rest of the table. It may not be realistic to deliver the final product, but many times we can do more than we think to help followers take the next step on their journey.

Remember this: when you win the heart, you get best of everything else a person brings to the table with them (hands, mind, energy, skills, etc.).

Excel at Execution

Without results, the rest of the discussion about leadership is pretty useless. What’s the point? Unfortunately this is where many leadership initiatives start rather than end. Still, excelling at execution is a leadership responsibility. One way to improve is simply sharing the score. People tend to work harder and smarter when they know where they stand.

If your team is operating at less than full potential, there’s room to improve your leadership execution. It may be up to you to raise the bar.

So how about you – are you playing chess or checkers?

Nathan Magnuson is an executive leadership consultant, speaker and author of the books Stand Out! and Ignite Your Leadership Expertise. Click to see the exciting ways Nathan is helping organizations and teams become more effective with Leadership-in-a-Box.