Average Managers Play Checkers; Great Leaders Play Chess

The difference between a good manager and a great leader often comes down to one thing: strategy. While both roles are essential, the ways in which they approach challenges, solve problems, and steer their teams can be worlds apart.Think of it this way: average managers play checkers, focusing on the immediate moves. Great leaders, on the other hand, play chess, strategically thinking several moves ahead to guide their team to long-term success. If you want your organization to stay relevant and agile, it's the chess players—those who anticipate change, understand their team members’ strengths, and align their strategies with future goals—that truly stand out.

Checkers vs. Chess: What's the Difference?

At a glance, both checkers and chess involve moving pieces across a board toward a goal. However, the depth of thought, planning, and foresight required in eachg ame couldn’t be more different.

Checkers is straightforward: you move one piece in one direction, reacting to what’s directly in front of you. It’s about making quick, short-term decisions and responding to immediate challenges. Many managers operate this way—focused on solving daily problems without much consideration for long-term goals.

Chess, on the other hand, is a game of strategy and foresight. Every move affects the future, and the best chess players think several steps ahead, carefully positioning each piece for success. Great leaders are like chess masters, anticipating obstacles, empowering their team members to perform in roles suited to their skills, and aligning daily actions with the team’s TKRs.

Average Managers PlayCheckers

Short-Term Thinking

Many managers are stuck in "firefighting" mode, constantly putting out immediate problems instead of focusing on the big picture. They aren’t focused on hitting the TKRs but on completing the day-to-day tasks that pop up. 

Task-Focused Over Vision-Focused

They might excel at delegating tasks and meeting deadlines but lack a long-term vision that motivates and guides the team toward bigger goals. They might not have TKRs or have too many that change frequently. 

Limited Understanding of Team Dynamics

Checkers-like managers often treat all team members the same, assigning tasks without understanding each individual's unique strengths and potential. 

Great Leaders Play Chess

Strategic Vision

Great leaders don’t just react to problems as they arise. Instead, they proactively plan for the future, identifying key priorities and aligning their team's efforts to meet long-term objectives.

Empowering Team Members

Like chess masters who carefully position their pieces, great leaders know their team members' strengths and weaknesses. They assign roles that align with these strengths, empowering individuals to reach their full potential. This job sculpting helps keep people engaged and motivated and provides a sense of ownership over their work. 

Big Picture Focus

While they understand the importance of short-term wins, great leaders always keep their eye on the broader vision. They’re constantly ensuring that each decision contributes to the overall growth and success of the team and the TKRs. 

Fostering Innovation and Ownership

Leaders who play chess encourage creativity and critical thinking within their teams.They give their team members the autonomy to innovate and take ownership of projects, much like skilled chess players anticipating the future by developing strategic options. Not only does this improve employee engagement and job satisfaction, it also prepares them to take on leadership roles in the future.This enables the manager to move up the ladder without fear that the team will flounder in their absence. 

Lessons from Chess for Great Leadership

Anticipation

Just as a chess player anticipates their opponent’s moves, great leaders foresee challenges before they arise. This allows them to be proactive rather than reactive, avoiding potential setbacks. This should be done as a group where possible. While the manager is ideally able to foresee certain issues, it’s important to get the whole team involved. This will likely happen during the alignment process. 

Patience

Leaders who play chess know that long-term success is often built slowly. They don’t rush decisions or chase immediate results. Instead, they wait for the right opportunities and make moves that will yield the best outcomes down the road.

Resource Allocation

In chess, each piece has a different role to play. Similarly, great leaders understand that not all team members are interchangeable. They take time to get to know their team’s strengths, weaknesses, and motivations to assign the right people to the right tasks. This won’t only improve the outcome of the task. It also improves retention, job satisfaction, engagement, and motivation.

Flexibility

In both chess and leadership, things don’t always go as planned. Great leaders are prepared to adapt their strategies when necessary, adjusting their plans to navigate unexpected challenges.

How to Shift from Checkers to Chess as a Leader

Develop a Strategic Vision

Move beyond the immediate and start thinking about how your team fits into the organization as a whole. When leadership has decided the goals for the company, tailoring the TKRs for the team to support those will make the goals a reality. 

KnowYour Team

Spend time understanding the strengths and weaknesses of each team member. This takes a concentrated effort during one-on-one and group meetings. Use this knowledge to position them in roles where they can excel, just as a chess master carefully moves their pieces.

Encourage Long-Term Thinking

Cultivate a culture that values long-term success over short-term wins. Encourage your team to think several steps ahead and to consider how today’s actions affect future outcomes. Don’t focus on the outcomes of the day when the focus of the team should be hitting the TKRs.

Empower Autonomy

Give your team members the space to make their own decisions and learn from their experiences. Like a great chess player, trust your pieces (your people) to make moves that contribute to the larger strategy.

The most effective leaders understand the value of playing the long game. They can steer their organizations toward lasting success by thinking strategically, empowering their team, and keeping an eye on the big picture. So, ask yourself:are you playing checkers or chess?

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