High stakes collaboration
Techniques for achieving infinite possibility in the context of finite games
In Finite and Infinite Games: A Vision of Life as Play and Possibility, James Carse wrote, “A finite game is played for the purpose of winning, an infinite game for the purpose of continuing the play.”
Carse's book provides a conceptual model for visualizing the nature of relationships and our role within them.
There are finite relationships, in which both parties are engaged for the purpose of winning a game. And there are infinite relationships, in which both parties are engaged for the purpose of playing the game for as long as possible.
Using Carse's model, I began to visualize and reflect on my relationships using the following form.
As I studied my relationships, I noted several observations:
Infinite relationships had no clear endpoint. Their implicit purpose was to go on forever.
Finite relationships typically had a clear end point (e.g. a contract end date); or were clearly zero sum (e.g. one party had to lose and one party had to win); or simply came to a natural end (e.g. a childhood friendship that didn't sustain itself through the full journey).
Cusp relationships could migrate to infinite or finite status, for example customer relationships, where the customer might eventually outgrow the service, but would remain a trusted advisor, or even move into the realm of infinite friendship. Or a teammate, who might work at the company for a couple of years and then move onto another role somewhere else, while preserving the personal relationship.
As Carse's model infiltrated my thinking over the last couple of years, I began to reflect on the degree to which I'd contributed to relationships that had proven to be finite when they could have been infinite, and began challenging myself to view all relationships, even those that were ostensibly, or temporarily zero-sum, as carriers of infinite potential.
I believe this is one of the goals of Carse's book – to prod us to consider the extent to which people can live happier lives and collaborate more successfully with each other when we view our relationships through the lens of infinite game theory rather than finite, or zero sum, game theory.
But, practically, how do people achieve on an infinite approach to relationships when the context of their collaboration is time-boxed, the intensity is high, and the stakes feel zero-sum?
3 Arenas
Imagine 3 scenarios. Each scenario comes with the prerequisite that you've done something good to get to where you are, but you're now facing a very pressing complication that you can’t mitigate without successfully collaborating with the other people living through the situation with you.
Sport – You're the captain of the US men's or women's national soccer team. The team has made it to the World Cup Finals and is playing against favorites Brazil. The score is 1-0 Brazil in the 55th minute, the Brazilians are dominating possession, your star player is having his/her worst game of the tournament, and the team's morale and performance is sagging with every passing minute.
Business – You're the CEO of a startup. The company has grown well and has raised its Series A, but due to a variety of factors, growth has started to slow, and you realize your revenue targets, which are essential for raising the next funding round, are at real risk. If you miss your revenue targets, you'll have to lay people off, disappoint your investors, and the paper value of years of hard work will effectively evaporate.
Family – You're a mother/father of a 14-year old who is skipping out on school and becoming a bad influence on your 9-year old. The complication has given rise to high-octane fighting with your 14-year old, something you never imagined when he/she was a child. To make matters worse, you're finding misalignment with your spouse. You both disagree about how to address the 14-year old's behavior, and these challenges are contributing to intense marital conflict.
The differences and similarities of these scenarios are best represented along two vectors: 1) the amount of collaboration time with the people who are in the foxhole with you; and 2) the amount of time you have to make a decision to change the direction of the situation.
It's easy to armchair quarterback situations like these. The captain should rally and inspire the team. The CEO should do an offsite to diagnose the core issues with his/her leadership team. The mother/father should seek alignment and also professional help.
But "should statements" like these don't provide techniques that we can weave into our decision-making muscle memory.
Over the last ~3 months, I've been working to help integrate two companies that joined via acquisition in late November. When two companies merge, the most significant risk to value creation is that the two cultures fail to successfully integrate.
I've understood this, in theory, but am learning on the fly how to apply that knowledge in practice, and I've come into contact with several ideas, which I think serve as effective techniques for application to the 3 scenarios above.
Hills we die on
The first of these ideas is the notion of not building a hill to die on, a relationship technique premised on flexibility and infinite game theory. My ability to apply language to this technique came about through Venkatesh Rao's recent blog post of the same name, which is excellent, and which I highly recommend.
The main thrust of the idea is that people set themselves up to fail at creating value together when they succumb to the need to have personal assessments of problems validated by the other party.
Hills to die on are usually created when one party bogs down in a self-inflicted rhetorical lament, "Why can't they see that I have the solution to their problem?"
As Rao notes, this fails because complex systems are almost never broken and everyone in the system is viewing the system based on different incentives. He writes, "systems thinking isn't a skill, it's a scope of interest."
Of the above scenarios, avoiding hills to die on is probably most useful in the context of the nuclear family. Should one parent conclude that there is only one path to helping the troubled teenager and then demand acknowledgement from their spouse that their diagnosis and prescription are alone in their validity, the outcome includes increased chances of divorce, not to mention, increased chances that the child's behavior takes a turn for the worse.
Free to spar
While running Matcha together, my co-founder and I achieved a high degree of comfort in the context of debate with one another. We were effectively sparring partners and grew to appreciate the ability to "go to the mat" over an idea and emerge with an even stronger sense of respect and trust.
As our sparring capacity deepened, we worked hard to make the comfort we felt in debate achievable for everyone in the organization. Achieving on that work required two perpetual inputs:
that the culture would enable people to eventually become comfortable with vulnerability
that people would be provided with techniques that helped them grow as communicators
On the first, we came to realize that vulnerability in companies is simply code for, "I can say something really dumb, and you will not look down on me or want to cast me out."
And on the second, we were able to find simple and useful frameworks, such as the Minto Pyramid Principle, that could be easily incorporated into the corporate consciousness and even more deeply into the company's value system.
Of the above scenarios, achieving comfort in sparring is probably most useful in the context of the World Cup soccer team. Sporting matches are high intensity affairs that demand of their participants the stiff upper lip necessary to navigate zero-sum intensity. Should the captain of the team find him/herself unable to challenge the under-performing star player with a sharpness commensurate with the stakes, it is unlikely that the collaboration can lead to a come back. If on the other hand, the captain can demand more of the star player, and the star player can rise to the captain's challenge, regardless of the tone and style of the delivery, the team has a chance to lift the sagging morale, regain possession, and attempt to come back from the brink.
Waterfall trust vs. agile trust
Writing about a failed early consulting gig, Rao writes, "My unhappy fourth gig taught me that initial trust must be converted to working trust by getting expectations aligned and crystal clear early on. But not through painful and structured conversations seeking “alignment” or clarifying “expectations.” That’s a waterfall approach to trust that basically never works because you just don’t know each other well, and end up making ritual noises. Instead, you do it by iteratively setting and delivering on small, bite-sized goals that get larger and larger."
In the context of developing software, waterfall product management approaches development via sequential linear phases with little budgeting for iterative testing along the way. Modern software companies are critical of this approach for its rigidity, favoring agile development, which advocates for more adaptive planning, iterative development, and avoidance of premature optimization.
Just as waterfall product development increases the risk of software failure, so too does a waterfall approach to trust. The waterfall approach to trust pays upfront lip service to alignment and expectations without subsequently getting into the foxhole together. In other words, it's easy for people to say, "We're aligned. I'm excited." It's much harder to then meet on a core complication and slog through limited data and disagreement to arrive at a solution both parties can commit to.
Ironically, lip-service alignment and passive aggression, both of which stem from a desire to avoid direct conflict often turn out to be fast tracks to turning what could be infinite games into finite games.
Of the above scenarios, avoiding waterfall trust is probably most useful in the context of the Series A startup. Building successful companies is one of the hardest things to do. It's especially hard to build a successful venture-backed company, as evident in the high failure rate. Startups are further challenged by having narrow operating windows within which they need to recruit people whom they typically have very little time to get to know before hiring. Should the CEO of the company find him/herself in a position where the team is paying lip-service to the company's goals, then everything will be more expensive. If on the other hand, the CEO can help to accelerate getting into foxholes together to complete real work, then the team has a chance to move as one toward the same objective.
Summary
Collaborating successfully in a high-intensity situation might be the defining characteristic of the human race. And reimagining our relationships through the lens of the infinite may position us for greater success in the context of our daily collaborations. But doing so is so much easier said than done.
Not building a hill to die on demands that we not succumb to our need for validation; that we remain flexible in the context of complexity.
Finding sparring partners is freeing and demands that we achieve a certain vulnerability & thick-skinnedness together.
A waterfall approach to trust never works – it's unrealistic and passive. Real trust emerges from the agile process of actively doing projects together.