After Endgame

Last weekend, I found myself at the Soho Playhouse in New York, watching a show called "After Endgame by Kevin James Doyle. While billed as a comedy about chess, it turned out to be something far more profound – a performer's journey through his adventures as a chess player and tutor, filled with international escapades and life lessons. As I watched him break down the game into its three fundamental phases – opening, middle game, and endgame – I couldn't help but see the parallels to leadership. His stories of triumph and failure, of careful calculation and bold improvisation, illuminated how these chess principles mirror our own leadership journeys. Through his lens, I began to see how every significant initiative we undertake follows this same pattern: the strategic planning of the opening, the adaptive challenges of the middle game, and the precise execution required in the endgame. These phases, I realized, offer profound insights into how we can better structure our approach to leadership challenges.

In chess, the opening is all about establishing a strong foundation through careful positioning and protective structures. Similarly, in leadership, our initial moves set the tone for everything that follows. When launching new initiatives or taking on leadership roles, we must thoughtfully position our resources, build supportive frameworks, and create a strategy that both protects our core strengths and provides opportunities for advancement. Just as every chess piece needs protection and purpose, every team member needs clear direction and support from the start. The opening phase is where we establish our culture, set expectations, and create the conditions for future success. It requires careful consideration of both offensive possibilities and defensive necessities, always keeping in mind that early mistakes can have long-lasting consequences.

The middle game is where theory meets reality, and our carefully laid plans encounter unexpected challenges. This phase demands real-time adaptation and creative problem-solving. As leaders, we often find our initial structures and strategies tested by market changes, competing priorities, or unforeseen obstacles. Success in this phase requires both tactical awareness and strategic flexibility. We must be willing to sacrifice some of our original plans while maintaining focus on our ultimate objectives, much like a chess player who gives up a piece to gain positional advantage. The middle game tests our ability to balance multiple priorities, manage resources effectively, and maintain team cohesion even as circumstances shift beneath our feet. It's where leadership truly comes alive.

The endgame, perhaps the most crucial phase, tests our ability to convert advantage into achievement. In chess, as in leadership, it's not enough to gain an edge – we must know how to bring situations to successful conclusions. This requires precision, patience, and the wisdom to recognize when to press forward and when to consolidate our position. Many leaders excel at starting initiatives or managing ongoing operations but struggle with the delicate art of bringing projects to elegant conclusions or effectively transitioning between phases of organizational growth. The endgame demands a clear vision of the final state we're trying to achieve and the discipline to execute with precision, even when fatigue sets in and pressure mounts.

In life and leadership, understanding these three phases helps us navigate complex challenges with greater awareness and intention. Just as a chess master must think several moves ahead while remaining present in the current position, effective leaders must balance long-term vision with immediate execution. For those we love and lead, our ability to master each phase – from strategic beginnings through adaptive middle games to decisive conclusions – creates a framework for sustainable success. Like a well-played chess match, leadership is ultimately about seeing the whole board while executing each move with purpose and precision, always remembering that our decisions impact not just the current moment but the entire game ahead.

With love, gratitude and wonder,

Scott