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On Leadership and Playing Long and Infinite Games

As leaders, we’re living in a world that constantly evolves, one in which we’re playing with a certain set of competencies and interests. The more aligned those competencies and interests are, the more enjoyable the game. And the more enjoyable the game, the easier it is to keep playing. If others  — a group or an entire industry — are playing the same game, we inevitably grow through learning about ourselves as we play the game with others. 

The problem with games we enjoy playing is they tend to suck us in. Worse, if we’re only playing one game, over the long run, it’s likely that the good players will move on to other games because they became bored and wanted a new challenge. To borrow a popular analogy, some are playing checkers, while others are playing chess. In that sense, those who moved on to other games are like the great chess players who decide to play multiple games at once. Or maybe they decide to master not just playing chess but also writing about its strategies as well. 

Point is, they’ve begun to evolve beyond the game others are playing. They moved from playing a game to playing multiple games, and then they began to think about longer games as well.

It can be argued that most people (and companies) play a limited number of short games, only focusing on the quick wins that stem from low-effort, high-impact activities. Too few invest the time and energy necessary to be great at multiple games, as well as the long game, which requires more work and more patience. The fact is, mastering numerous games and playing long games both offer huge advantages. 

If you do what everyone else is doing, you shouldn’t be surprised to get the same results everyone else is getting.” — Peter Kaufman, investment banker and private equity investor.


Long and Infinite Games

Successful people in any field all play some version of the long game. Good companies, in my opinion, play long games, whereas great companies play infinite games. 

Both good and great companies think well ahead, planning for goals and opportunities that may extend beyond the tenure of their current leadership teams. Some of these goals are stretch goals, or Compelling and Audacious Goals (CAGs), as we call them at Ninety. However, those playing the long game are focused on ultimately achieving an end goal (winning), whereas those playing the infinite game do so in perpetuity, always basing their decisions on advancing the company’s Just Cause. 

This takes work, foresight, and fortitude. And those are just a few of the many reasons people don’t play long, or infinite, games. Playing the infinite game means that a company must successfully overcome some of these common impediments: 

  • Short attention spans and impatience
  • Apathy or disinterest in thinking about how the game will evolve
  • Insecurity
  • Ignorance 

Of course, the ideas associated with long and infinite games aren’t particularly novel. People have written about them for years, with Simon Sinek’s 2019 The Infinite Game as a notable example.

In fact, from the outside, the long and infinite games look boring. The tiny advantages that accrue aren’t noticed until success becomes too obvious to ignore, or it’s so far away that we could never catch up.

Short games are about efficiency. They make it easy to keep our heads down, completing tasks as if by rote. But they rob us of creativity and perspective. They slowly and eventually turn most of what we're collectively doing into drudgery.  

That’s what makes short games so easy to get sucked into. They make it easy to put off anything that seems hard or where the reward seems far away. Examples of short games include:

  • Not developing a long-term plan
  • Not being intentional about building a high-trust culture
  • Not saving for a “rainy day”
  • Not building high-trust relationships with each of our ideal stakeholders
  • Not taking time to celebrate our wins or properly appreciate our team
  • Not investing in our people's growth

The more we opt to play the short game, the further removed we are from being able to get into the long games that might be interesting to us. Unfortunately, we’ll find the game has moved on; it’s become more nuanced and complex, and it's attracted a different set of players. The rewards are now higher, as is the bar to play. Only when the costs become too large to ignore do we realize we stayed too long in the wrong game. And then, for many companies, it may be too late.

As leaders, we'll never build a great company if we don’t play an increasingly longer game. We know all about the stages of organizational development, and the larger our organization, the more likely it is we need to play a longer and longer game. If you, as a leader, want to build a good — let alone great — company, you need to be playing at least a 5- to 10-year game, and your direct reports need to be playing 1- to 5-year games.

For others in your organization to follow suit at appropriate intervals, I deeply believe we need to teach and coach every one of our employees the power of long and infinite games. 


Sustainability > Short-Term Wins

Long and infinite games allow us to compound results. The longer we're at it, the better we do and the greater the rewards we accrue. Playing long and infinite games requires sacrificing a bit of today for a much bigger tomorrow. 

Perhaps that’s why it’s so difficult for some to adopt that mindset. At an individual level, the long and infinite games can appear boring. Here are a few examples of what it might look like:

  • Focusing on healthy habits
  • Resisting temptations, vices, or anything we know to be detrimental to our physical or mental well being
  • Investing in our relationships every day so there’s always a solid foundation of support in good times and bad
  • Taking time for reflection, whether that’s through reading, journaling, meditation, or other means

At the company level, playing the long or infinite game looks like this:

  • Paying team members fairly
  • Creating a culture that rewards “we” not “I”
  • Investing in people
  • Being as transparent as possible — about everything
  • Sharing a fair percentage of our profits with Ideal Team Members, or letting them invest in our equity
  • Creating a clear and compelling vision that is big enough for our dreams and those of our Ideal Team Members
  • Moving away from managing — instead leading and coaching (pdf opens in a new browser tab) our team members

It all comes down to this: I firmly believe we’re moving into a New Age of Work, and playing the long and infinite games is going to be required if you want to be able to attract and retain your version of Ideal Team Members

The power of long and infinite games isn’t debatable. It’s fairly obvious that at some point in our lives, as individuals and as great company builders, we should start to save for a rainy day, anticipating a time when we’ll no longer be interested in and/or capable of Work. Anticipating a time when we have to pass the responsibility of leading on to the next generation. 

The first step is the hardest. We have to be willing to sacrifice today to mitigate the likelihood of suffering in the future. This is why so few people play the long game.

How Will You Lead? 

Leadership includes having a strong point of view about where we are going and why. Leadership requires decision-making. Our decisions lead to action or inaction. Inaction inevitably leads to decline. Action can be to just keep doing what we’re doing. I hope my thoughts on doing the same thing over and over again are clear, but just to be thorough — it’s not good.

As a leader, you can’t “opt out” of owning your company’s future. You also can’t play a long-term game in everything. Leaders have to be crystal clear on what matters. We’ve been studying and coaching leaders for decades. Getting clear on what matters is not that hard. But if you're not entirely sure, it will be helpful to download our guide, On 9 Core Competencies, and take some time to reflect on it.  

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