Medium 9781626563940

Chess Not Checkers

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As organizations grow in volume and complexity, the demands on leadership change. The same old moves won't cut it any more. 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!

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Leading has never been easy. From our first experiment trying to get our classmates to follow us or receiving our first official assignment at work, leadership has always demanded our best effort. That hasn’t changed—but something else has: the complexity of the problems we face and the organizations we lead has increased exponentially.

Perhaps this complexity finds its energy in the scope of your enterprise, or it may merely be a function of increased volume. These are great problems to have … if leaders can orchestrate an appropriate response.

Unfortunately, for many leaders, our past successes just don’t translate. The game has literally changed before our eyes. The methods that worked extremely well in the past no longer have the same effect. In many cases, the tried and true has become the tired and tarnished.

Most of us began our leadership journey utilizing an approach with striking similarities to the game of checkers, a fun, highly reactionary game often played at a frantic pace. Any strategies we employed in this style of leadership were limited, if not rudimentary. The opportunities in our world for leaders to play checkers and be successful are dwindling.


The Decision


If you miss the “opportunity of a lifetime,” do you ever get another one?

Blake wrote these words in his journal, put down his pen, and stared out the kitchen window. He had gotten up early; he couldn’t sleep, anyway. His mind was racing as he reflected on his life and career up until this point.

The last decade had been a whirlwind. After his father died, Blake had invested five years trying to live up to his dad’s expectations. Jeff had always believed his son could lead. Blake had never been sure, but he pushed through his doubts and dedicated himself to learning the skills of leadership.

Blake’s leadership journey had been frustrating. After learning to cast vision, build teams, get results, and more, he had been passed over for formal leadership positions. Confused by this turn of events, he reached out to his longtime mentor, Debbie Brewster. She helped him gain the greatest insight of his life thus far: If your heart is not right, no one cares about your skills.


Harder Than It Looks


Blake made the call and signed the papers. He went to his boss at Dynastar and announced his decision. Then he told his teammates. He shared that he had stumbled on the opportunity of a lifetime and felt like he needed to give it a try. All these conversations went surprisingly well, and everyone was extremely encouraging.

On Monday morning, Blake drove to his new company. He arrived early—early enough to be the first one there. With a little convincing, a security guard finally let him in since Blake didn’t have keys yet.

While waiting for the day to officially begin, he sat at his desk and stared at his new laptop. Just as he realized he didn’t know the password, his thoughts were interrupted by a knock.

“Good morning, sir. I’m Suzy, your assistant.” She stopped and then added, “Or I hope I will be.” Her voice trailed off.

A middle-aged Asian woman, Suzy was wearing a long-sleeved T-shirt, handmade beaded necklace, and sweat pants; she finished off her ensemble with large glasses with bright red frames. She was clearly underdressed for the office by Blake’s standards. However, he chose not to say anything about her appearance on their first meeting.


Something Has to Change


Debbie Brewster was the third-most influential person in Blake’s life. After his mom and dad, Debbie had invested more in him than anyone else. She taught Blake how to lead. And the irony of it all was that since Blake’s late father had mentored Debbie, many of the principles she shared with him came, indirectly, from his dad.

Regarding his current challenges, Blake had complete confidence Debbie could help. He called her and she agreed to meet early the next morning. They met in the coffee shop they had used as a central meeting place on and off for a decade.

“Good morning!” Debbie said as soon as Blake walked through the door.

“Good morning to you,” he said.

“How are you and Megan and the kids? We’ve got a lot of catching up to do,” Debbie said.

In no time at all, the two friends had reconnected. After a few minutes, Debbie said, “When you called, you said you had a new job. You’re a CEO now. Congratulations! How’s it going?”

“Well, it looks like it’s going to be really challenging,” Blake confessed.


A Different Game


On Thursday morning, before Blake left his house, he did a quick Google search for Jack Deluca. He quickly learned Debbie had understated Mr. Deluca’s accomplishments. He had not only led a wildly successful global organization but also served on several presidential task forces; he was a major donor to numerous universities, and he was named the most admired CEO by several magazines over three decades. All of this fueled Blake’s desire to be a little bit early. He didn’t think Jack was a man you wanted to keep waiting.

When Blake got to the park, he began to walk. He wasn’t exactly sure what he was looking for, other than a crowd. He walked past a large playground and then he saw about twenty-five people standing around a picnic table. He couldn’t see who was at the table but assumed it was Jack.

He pushed his way through the people surrounding the table to see what was going on. Two men stared at a chessboard. One man was in his early twenties; Blake recognized the other man from the media photos: Jack Deluca.


Game On!


Back at the office, Blake was anxious to share his newfound insight with the team. Already, he could think of many situations in which he and the team were clearly playing checkers.

On Monday morning, Blake arrived earlier than usual. He went to the conference room and set up both a chessboard and a game of checkers. When the team began to arrive, the comments were fun to hear.

John was the first to arrive. He looked at the table and said to Blake, “Looks like the staff failed to clean up after game night.”

Brad and Angie walked in together. Brad sighed, “This is probably some lame team-building activity.”

“Well, we should be good at it, because we’re a pretty lame team,” Angie said with a grin.

As Blake listened to each disparaging comment, he maintained a good spirit and chuckled with each jab.

After everyone was seated, Blake began. “Thanks for being here this morning. I know it’s been difficult for you guys with the revolving door for CEOs over the last decade. My goal is for us to work together to make this a great organization.”


Start Here


As Blake drove the two hours from his home to the park, he thought about the big idea from the last meeting: chess, not checkers, is the key to leading a high performance organization. He knew there was much to do, but he had no idea where to start. He was hopeful Jack’s four “moves” would make his path forward much clearer.

As he arrived at the park, the scene was almost identical—only the player across the table was different. When Blake made his presence known, Jack made one move and said, “Checkmate.” Again, the opponent looked stunned, and the small crowd began to applaud.

“Thanks for coming. I’ll be back next week,” Jack said with a huge smile, shaking hands with a few members of the crowd as they departed.

As the last person walked away, Blake sat down and said, “That was strange.”

“Really? Which part?”

“It was just like two weeks ago. Does it always end like that?”

“Like what?” Jack asked.

“Do you always win?”

“Here in the park I do, but not always.”


Place Your Bet


On the ride home, Blake began to think about all he’d learned in the first few months on the job. He realized leading a large and complex enterprise requires a different level of leadership. “Chess not checkers” made perfect sense conceptually. His challenge now was to figure out what it looked like in the real world. His conversation with Jack was extremely helpful. He believed his team could turn Jack’s ideas into plans and tactics that would work. He was about to encounter his first real test.

On Monday morning, the team assembled at 8:00. This was beginning to feel normal, even to Elizabeth, who was not a morning person. She had already lobbied several members about moving the meeting to 8:00 p.m. The group politely declined.

As the team gathered, Blake could hear a couple of conversations around the table. It sounded to him like they were talking about chess!

“Good morning! I trust you’ve had a good weekend. I hear a couple of you talking about chess; we’ll get to that in a moment. First, I have asked Brad to help us develop a process we can follow to create next year’s plans. Brad, please give us a quick overview.”


What’s Important?


Word spread quickly throughout the business that John was leaving. Of course, the company would be discreet and offer a statement indicating John’s decision to “pursue other career options.” Although that was true, Blake decided he needed to tell his team the rest of the story. So he called a special meeting for the following morning.

Just before the meeting was scheduled to begin, everyone shuffled in without saying a word. They just took their seats and looked at their new CEO, waiting for an explanation. Blake was sensitive to the mood because everyone, including Blake, had liked John.

“Good morning. I called this meeting because I know we need to talk about John’s departure.”

After an awkward silence, Angie said, “What happened? John had worked here for years.”

“I know. I hated that he decided to leave.”

“Did he really, or did you fire him?” Brad asked.

“No, I didn’t fire him. I outlined what I expected from a member of my senior team, and he said he didn’t want to be part of it. I respect that.”


Who Cares?


For the first time in his short career as a CEO, Blake felt like the team was finally on track. If he was honest with himself, he was embarrassed it had taken him several months to get this far. Thank goodness Debbie had introduced him to Jack. The “chess not checkers” moves Jack was suggesting were easy to understand and communicate. He knew what Jack was teaching him would take time to fully implement. But at least for now, he felt the team was on the right path.

It was time for Blake to meet with Jack again. The team had already begun to implement ideas around Bet on Leadership and Act as One—they were making progress! Blake was energized as he thought about his upcoming meeting.

Once again, the park was relatively empty—except around Jack’s table. Again on this morning, Blake found Jack playing a game with a small crowd watching. After Jack spotted Blake, it took several moves before he made his final move and announced, “Checkmate.” And, as usual, the bystanders went wild—this was not a typical chess crowd.


It’s Your Move


The business continued to improve—or so it seemed. The team was now interacting between meetings. Suzy was doing much better than anyone expected. She was open to feedback, and she asked outstanding questions. Blake hired a temporary assistant, Alex, so Suzy could focus on her new role. Then, on the day before Blake’s next meeting with Jack, things took a turn—a big turn—for the worse.

Blake had arrived early to slay the email dragon before it grew in strength. He had made several positive changes over the previous weeks, and the number of messages was steadily decreasing. His team now owned many of the issues once funneled directly to him. From his perspective, this was a very good sign. However, quite a few messages still made their way to him. This morning, he found one that captured his full attention. The subject line read, “We’re Done!”

As Blake quickly read the message, his heart rate increased. He scrolled back to the top to confirm the sender—unfortunately, it was their biggest client. They were leaving. They were not satisfied with the service, the product, or the attitude of Blake’s company.


Game Plan


On the way back to the office, Blake called Alex. “Please see if everyone on the leadership team is in the office today. If they are, call a meeting for 2:00.” Although Blake believed the business was generally headed in the right direction, he agreed with Jack—they needed more focus on execution.

At 2:00, Blake began. “Thanks for coming on such short notice. I had a good meeting today with Jack, and we talked about the fourth move we need to make to create a high performance organization—Excel at Execution.”

“Isn’t that what we’ve been working on?” Charles asked.

“Yes and no,” Blake said. “The yes part: we are making good plans and laying the groundwork for the future. The no part: we are not moving with enough urgency. Our conversations have been focused on the first three moves, and we’ve not done enough to improve our execution. Regardless of what we’re working on, we can never forget we must execute. Ultimately, we want to excel in this arena. Right now, we’re playing catch-up.”


What’s Next?


In the weeks leading up to the planning retreat, a new energy swept the company. The leaders were talking with their team members about what was important and how they might keep score. The ideas generated were diverse—some more creative than others. But all the metrics were effective in letting everyone know the score. They included time to fill a customer’s order, accuracy, returns, waste, and overall customer satisfaction. On the Marketing team, Suzy led the group to think beyond sales to the source of sales; they set goals around sales from new customers as well as existing customers. They also decided the size of the order was a good metric to consider. All in all, Blake was pleased. Real, substantive conversations about the business were happening all across the organization.

Blake was also glad he had another meeting with Jack before the retreat. They met in their usual place, and, yes, Jack was playing chess when he arrived.

After the game, Jack said, “Did you make any moves since we last met?”




The next six months were crazy, frustrating, exhilarating days for Blake and the team. There was so much to do that the team ultimately decided they needed to scale back the plan for the upcoming year. They didn’t abandon any of the moves; they just decided to implement their plan a little more slowly—“narrow the focus,” as Jack would say. This made the implementation of their ideas much easier.

Performance continued to improve. In retrospect, it made perfect sense—if you invest in your leadership; ensure the entire organization understands your purpose, mission, and values; leverage people’s strengths and help them pursue their dreams; and create systems to enable great performance. It works!

The most frustrating part of the entire journey was the realization some of their employees didn’t want to play chess—they were more than happy with checkers. Those people had to go.

As the company grew stronger and stronger, its reputation and market share grew as well. So much so, Blake was surprised to get an email from Sam, the client they had lost almost a year earlier. It said, “Call me.” Blake did and that call led to a visit, and that visit led to a restored relationship. Blake and the team had their biggest client back.



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