Book Summaries

Book Summary – Chess Not Checkers: Elevate Your Leadership Game by Mark Miller

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If you try to play checkers in a chess world, problems are your reward.

Chess is not a game of luck, and neither is business. When you win, it’s because you made good decisions.

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I am fascinated with the game of chess, even though I do not know how to play it yet. It is on my bucket list of games to master; the game contains lots of strategies that are applicable in life and business. I have seen lots of movies (Searching for Bobby Fischer, Life of a King), Documentaries (Magnus, Game Over: Kasparov and the Machine), read some books such as How Life Imitates Chess by Gary Kasparov to name but a few.

Chess Not Checkers by Mark Miller is an excellent book on how we can apply the game of chess to win in business. The author share four Chess Moves that have Parallel to Business, these moves, derived from winning strategies and principles from the chess world, have parallel applications in any organization. The four chess moves are: Bet on Leadership, Act as One, Win the Heart, and Excel at Execution.

In Chess Not Checkers, Mark Miller tells the story of Blake Brown, newly appointed CEO of a company troubled by poor performance and low morale. Nothing Blake learned from his previous roles seems to help him deal with the issues he now faces. The problem, his new mentor points out, is Blake is playing the wrong game.

The early days of an organization are like checkers: a quickly played game with mostly interchangeable pieces. Everybody, the leader included, does a little bit of everything; the pace is frenetic. But as the organization expands, you can’t just keep jumping from activity to activity. You have to think strategically, plan ahead, and leverage every employee’s specific talents—that’s chess. Leaders who continue to play checkers when the name of the game is chess lose. 

On his journey, Blake learns four essential strategies from the game of chess that transform his leadership and his organization. The result: unprecedented performance!

Here are my favourite take aways from reading Chess Not Checkers: Elevate Your Leadership Game:

 The game of chess contains four specific parallels that can inform and transform any organization seeking new levels of performance.  The author shares the ideas as a “move” an organization can make to draw closer to its goals. Collectively, these moves can be your blueprint for sustained high performance.

 If your heart is not right, no one cares about your skills.

On Mentorship

  • Most of us need multiple mentors in our life. Someone who can coach, encourage, and counsel us in one arena may not be best suited to do so in another.

Chess vs Checkers

If you want to lead a high-performance organization, you’ve got to play chess, not checkers.

 If you play checkers when the name of the game is chess, you lose.

  • The two games are played on a very similar board.
  • The color is different, but that’s just the beginning—the games that are played on these two, similar boards are vastly different.
  • Most small businesses can be successful with a checkers mindset. That’s actually the game you play when an organization is in start-up mode. The leader does virtually everything in the beginning. That’s checkers. Then, if you grow, you begin to add staff. Many leaders see these additional people as interchangeable pieces, nothing more than hired hands, no need for specialists. Each piece is capable of the same limited moves. That’s checkers. In the beginning the game is simple. That’s checkers. You react, you make decisions, the pace is frenetic—you’re playing checkers. And, it works … for a while.
  • You can win in business by playing checkers until someone sneaks in one night after you’ve closed for the day and flips the board. The game changes, and you don’t even know it.
  • The change can be subtle in the beginning. When your board gets flipped, you have the same products, customers, equipment, and employees. Initially, it’s easy to miss the change. Besides, when leaders are focused, we can become color-blind. The chessboard and checkerboard look identical other than their color. If you’re not looking for it, you can miss the change.

We can be so focused, we can actually become color-blind. We don’t even know the game has changed.


  • Chess is a game of choices, and business is, too. We win or lose based on our choices and how well we execute against those choices. Planning is where we make those fundamental choices.

Clues the game has changed

  • One of the signs the game has changed is a myriad of problems—problems that reoccur; problems that should have been anticipated and avoided, problems that catch us totally by surprise and we should have seen coming, and problems that are created by lack of focus or a failure to execute.
  • All of these are clues. When we see this happening, the methods we’ve used successfully in the past have to be reevaluated.

One of the signs the game has changed is a myriad of problems.

 The Four Chess Moves that has Parallel to Business

  1. Bet on Leadership: Growing leaders grow organizations

You can’t wait until you need a leader to start developing one.

  • In a high-performance organization, one way to apply this idea is to proactively develop your leadership. The earlier in their career you invest in them, the better. You can’t wait until you need a leader to start developing one. All high-performance organizations do this.
  • You cannot be a great organization without great leadership. All the moves are critical, but this is the first among equals. Leadership growth always precedes organizational growth.
  • The quest for high performance always starts with the leader—so does Bet on Leadership. You have got to set the pace for your team. People do what people see. If you’re not learning and growing, don’t expect them to, either.
  • Good chess players, and good leaders, think about the current move and the next move also—often several moves ahead. When you invest in emerging leaders, it means you’re serious about creating the future rather than just hoping it works out.

    Why Bet
  • You can’t be sure your investment in individual leaders will pay off. Some will rise to the challenge; some won’t. Some leaders stay with the company and others leave. However, high-performance organizations make the bet. They know if you can’t grow your leadership capacity, you’ll never reach your full potential as an organization.

2. Act as One : Alignment multiplies impact

A unified assault is always preferred over a fragmented one.

  • Act as One is about getting everyone in your organization pulling on the rope in the same direction. That’s a prerequisite to unleash the full potential of your business. Getting everyone aligned can have a phenomenal impact on your performance.
  • Here’s how this principle plays out in the world of chess. Imagine you want to attack one of your opponent’s pieces. To do so effectively requires focusing multiple resources on that single piece. To attack with one is futile—your piece will be lost. As a result, the best players don’t usually attack on too many fronts simultaneously. That approach spreads needed resources too thin and is not a winning strategy. To randomly attack—a piece to the left and one to the right—applies little, if any pressure, on your opponent. You’ve got to make your pieces work together to maximize your assault
  • It is hard to imagine leaders who ask people to give their best without helping them know what success looks like“Or, why it matters,
  • Decide, agree, and communicate.

One, decide what’s important to you.
Two, get agreement from your leadership team.
And, finally, begin an orchestrated effort to cascade and reinforce these messages throughout your organization.

  • Often the leader is clear on what matters most, and his or her key leaders know, too—and yet everyone else remains in the dark. The information never reaches the front lines in the organization. This is a colossal leadership mistake. You can’t harness the power of everyone unless everyone is in the know. You will never really Act as One unless you master cascading communications!

You will never really Act as One unless you master cascading communications!

3. Win the Heart: Engagement energizes effort

The more you can leverage the unique capabilities of each piece, the greater your chances of victory.

  • In checkers, the pieces are basically interchangeable; each is allowed to move only on the diagonal squares. In chess, there are different types of pieces, each with its own unique moves.
  • To be successful in chess, you want to understand and capitalize on these differing and unique capabilities. Here’s the principle: The more you can leverage the unique capabilities of each piece, the greater your chances of victory.
  • When people are given the opportunity to do what they do best, you engage much more than their hands. When you allow people to contribute their unique gifts and ask them to work from a place of personal strength, you do much more than get work done—you honor them and their contribution.
  • To Win the Heart is a process. To further complicate matters, when you are trying to win someone’s heart, one size doesn’t fit all. Activities that will raise one person’s engagement may not work with someone else.

 If you have a manager’s mentality, you tend to treat people all the same. Leaders understand if you want to bring out the best in each person, you must treat them differently.

  • Anyone whose heart you want to win. Every person on your team, from the most junior to the most senior, wants to know ‘Do you care about me?’ When they know the answer to that question is yes, they tend to reciprocate—caring begets caring.

4. Excel at Execution: Greatness hinges on execution.

To improve execution, be sure your business is built on systems, not on personality.

  • Systems are replicable—personality is not. You don’t want something to be done with excellence only because a certain person is doing it. As an example, you don’t want a selection process that works because one person makes good people decisions—that’s checkers. What if that person leaves or dies? You want to build a system capable of making good people selections—that’s chess.
  • Just like in chess, you will need to think deeply, choose wisely, and act decisively; every move counts. Excel at Execution—that’s how you ultimately win the game. It’s not the team with the most elaborate game plan; it’s the team that can successfully run the plays they call. And, they don’t just win—they become champions.

Attack the gaps

  • This idea of high performance is really not something you ever fully realize. Once you think you’re finished, you’re finished. The competition is not sitting still. If you stop, or sometimes, all you have to do is slow down, the competition will blow right past you. High performance is a lifelong pursuit fueled by personal and organizational learning.

Chess is not a game of luck, and neither is business. When you win, it’s because you made good decisions.

  • In chess, the more pieces you involve in the game, the greater your chances of winning; in business, including more people has the same effect. People want to be valued; they want to be useful; they want to contribute.

All the best in your quest to get better. Don’t Settle: Live with Passion.

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Lifelong Learner | Entrepreneur | Digital Strategist at Reputiva LLC | Marathoner | Bibliophile |

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