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TBM 229: Winnable and Unwinnable Games (Part 3)
CEO: I don't care what you do...just fix it! What support do you need?
CTO (thinking): I'm not exactly sure what we need, let me ask the VP.
CTO: I'll have a plan by the next meeting. I appreciate your support.
CTO (to VP): What do you need? I need to frame my ask to the CEO.
VP (thinking): I'm not exactly sure what we need, let me ask the Director.
VP (to Director): What do you need? I need to frame my ask to the CTO. Director (thinking): I'm not exactly sure what we need, let me ask the Manager
Director (to Manager): What do you need? I need to frame my ask to the VP.
Manager (thinking): I'm not exactly sure what we need, let me ask the Team.
Manager (to Team): What do you need? I need to frame my ask to the Director.
Team: Well,... [long detailed list of issues, needs, problems, etc.]
Manager: How much of that is really a problem? What is the MOST important thing?
Team: Um, it is all important, but [one thing]
Manager: How long exactly will that take? I need to know what to say no to.
Team: Um, we're not exactly sure, maybe, um, one month?
Manager (to Director): So if we fixed [simplified version of one thing] things would improve. It will take one month, or less because we can cut scope I think, and you know those engineers, always gold-plating
Director (to Manager): This looks really complicated. I need some bullet points please.
Manager (to Director): Um, ok, but, ok, so like three bullets?
Director (to VP): So if we fixed [further simplified version of one thing describe with three simple bullets] along with [simplified versions from other teams] things would improve. Together they should take three weeks.
VP to CTO: So we have the set of things that will really move the needle here. Across 8 teams. I've summarized it here in these 3 bullets each with 3 sub bullets. We need four weeks. Plans are set.
CTO (to CEO): We need three OR four weeks! I promise, this is the last time we'll need to put the brakes on things. We'll work down debt, and then things will be better.
CEO: Thank you. Hopefully this will help the engineering org build some confidence with the rest of the company.
Each person in the hierarchy (CEO, CTO, VP, Director, and Manager) acts as both an agent (when fielding requests from above) and a principal (when delegating tasks to those below). They are all trying to do their job while navigating constraints—minimizing their risks while maximizing their rewards. There's negotiation, occasional alignment, and occasional friction, and the scenario plays out repeatedly, causing a ripple effect and amplifying incentive and information asymmetries. See the principle-agent problem.
Individuals base their decisions on their predecessors' actions, with the probability of the wrong initial decision amplified through the hierarchy. It's a classic telephone game (with power and motives mixed in). Each decision maker simplifies and condenses the information to present to their boss ("got to keep the slide simple"), losing context and detail. By the time the turn is over, the complex issue is oversimplified, and you have an unwinnable game—at least from a global perspective.
Even in ideal circumstances, the information will degrade. When passing information up the chain, each agent simplifies the details to make it more digestible. There's a lot of information shaping—emphasizing and de-emphasizing things based on the audience. When requesting information, each principal probably injects a sense of urgency. By citing THEIR boss ("I need to get this ready for X"), they are already tilting the conversation in a particular direction.
Let’s challenge the idea of an unwinnable game for a moment. As noted above, maybe that is just at the global level. Each principal-agent interaction is its own game with its own rules and “spirit of the game”. There’s a strong likelihood that the high-level game could be a disaster, and meanwhile lots of people get promoted. Meanwhile, the “glue people” in the organization who see this all unfold may get psychically damaged by the sheer predictability of how this plays out.
Good Game Criteria Review
Let's review our "good game" criteria:
❗Clear, attainable goals that players understand.
This Game: The goals become watered down very quickly. Apparently it is to fix the problem, but the problem is unclear (even if it is clearly understood at some point).
❗Maintain a balance of difficulty, ensuring challenges aren't overly easy or excessively hard.
This Game: Ripe for teams overcommitting or commitments getting distorted. You can get yourself into a mix. One option is to under-promise, but that isn’t fun.
❗Timely feedback and rewards boosting player motivation.
This Game: Feedback loop is very, very long. Easy to get demotivated.
❗Engaging gameplay mechanics captivate players and sustain their interest.
This Game: Kind of soul-sucking. Everyone is passing along information with low confidence it will make a difference.
❗Signs of small victories or incremental progress can motivate them. This could be through progress bars, intermediate rankings, or minor accomplishments.
This Game: They are setting up a "quick fix," so there are no signs of incremental progress.
❗Meaningful choices that impact the outcome, fostering player agency.
This Game: Each player has low confidence their reply will impact the outcome—especially if they fear the message getting distorted.
❗Immerse players in a compelling environment or narrative.
This Game: The environment is not compelling. The narrative is not compelling.
❗Calibrate progression and learning curves, promoting mastery over time.
This Game: The feedback loops are so long and noisy. It is hard to calibrate.
❗Variety in challenges, environments, and mechanics keeps players engaged.
This Game: The challenge is very repetitive, with poor mechanics. Each time you pass along the information, you assume a poor outcome. There’s no real variety in the challenge.
❗Social interactions, such as cooperative or competitive play, enhance the gaming experience.
This Game: The principals and agents are not exactly cooperating. The Team is likely socializing, but they may have a “hunker down” mentality.
❗High replayability ensures the game remains fresh and exciting for repeated plays.
This Game: Replayed often, but not willingly. It never feels fresh. The game is exactly the same with the details of the fire changed.
How might we improve the game? Reply in the comments. Ideally, cite one of our "good game criteria".
Also, if this type of multi-part series interests you and you want me to continue this exploration, please leave this post a ♥️. I will keep going if there is enough interest.