Everything is so difficult, slow and cumbersome in a great organization

You’re a member of a team that is part of a large organization. Welcome! This post is intended to help you navigate your environment.

If you’re fresh out of school, or if you haven’t worked in a large organization before, you may not have experienced the difficulties that naturally arise when cooperating with other humans to carry out complex multi-participant tasks.

Why is everything so hard? Why can’t things just work?

The Prisoner’s dilemma is the reason. There might be a way of doing complex multi-participant tasks that is better than what’s being done currently, but the incentives for each participant are not aligned. Even when that lack of alignment produces a suboptimal outcome, each participant in the process lacks skin in the game. Each participant in the process creating the suboptimal outcome is not accountable for the consequence of their collective action.

Three potential solutions:
break the Prisoners dilemma through immediate exposure for every participant to the full consequence of outcomes.
–> In practice, this feels unfair to each process participant because they see the outcome as at least partially attributable to others in the process. Dividing responsibility among participants limits exposure to consequences.

break the Prisoners dilemma through coordination among participants.
–> In practice, communication takes times and skill; not everyone is willing to invest in communication that is seen as not “doing the work”. Additionally, accounting for the Allen curve takes effort. Lastly, the time needed to arrive through consensus at an optimal approach for a given situation may exceed time available for solving the problem.

break the Prisoners dilemma by limiting everything get done by one person.
–> In practice, this hero-based approach is limited by the attention-bandwidth of the individual and by the skill of the individual. As the complexity of the task increases, the skills needed by the hero increases, and the number of candidate heroes decreases. Large organizations accomplish complicated tasks by leveraging many average people in multi-step workflows.

As though that were not bad enough, in some organizations there’s a separate compounding problem: limited resources. For an organization, attention resources are {time, money, staffing}. In that case you get to layer on the negotiation for resources among competing teams within an organization.

Of the three options, coordination is a common response.

Why do we have so many meetings? Do I have to read all these emails?

Some meetings could be summarized in an email, or at least prepared for better. However, for people who don’t like to write, and for people who don’t like to read, meetings offer an easier (though more time intensive) alternative.

We can’t all communicate concurrently to establish consensus, and we are not all using the same strategies. That puts us in the
So we might exist in some Nash Equilibrium, it’s just more complicated than you might want.


Everything above applies in a static environment. A real organization is not static. Policies change. Business needs change. Technology changes. The competitive market evolves. Roles change as individuals mature within a team. There is turnover on the team roster. Processes depend on who is available and what skills each participant has.

Your knowledge of an organization’s processes has a half-life. The social network that you build has a half-life. As a consequence, you need to constantly invest in creating and renewing your social network within the organization.

But why can’t my Monday be more like my Sunday?

Confusingly, there seem to be counter examples to what I’ve been talking about. You likely use services in the real world on a daily basis provided by mega corporations. As examples, you use seemingly simple websites to accomplish tasks like “search the entire internet” or “find and deliver any product I can imagine to my house” or “connect every person on the Earth.” How is it that mega corporations can do that, but the organization you are in struggles to do what seems like simple tasks? Their websites are reliable, and your organization is unstable.

Those websites intentionally obfuscate the complicated coordination required. Those teams struggle with the same multi-participant Prisoner’s dilemma any organization does. How do I know that without working there? Because ideally they would hire a limited number of really smart people to avoid incurring Brook’s law. However, given their organization’s internal objectives, they are forced to build huge workforces to accomplish what seems like “simple” tasks.

A software developer could write a proof-of-concept search engine in a few days; Alphabet employs 130,000 people [source]. A software developer could write a simple e-commerce website in a few days; Amazon employs 1,335,000 people [source]. A software developer could write a simple social network website in a few days; Facebook employs 58,604 people [source].

Based on those numbers, I speculate that similar dynamics arise when carrying out complex multi-participant tasks.

Mitigation strategies

To recap, accomplishing complex tasks involves many people. When processes depend on more people than any participant knows, diverse incentives can results in outcomes that appear inefficient when viewed holistically. The situation can be made worse if there are insufficient resources for the organization’s participants. Communication can help but won’t necessarily yield an optimal outcome. Change exacerbates the difficulties. What I’ve described is generic to any large organization.

Rather than end on a dour note, I’ll describe how I’ve learned to progress.

  • Use mathematically-backed strategies in relationships
  • What would stunningly good communication look like? Do that.
  • Learn everyone else’s incentives and share my own with everyone
  • Read the literature on bureaucracy — this isn’t a novel problem.

The value of thinking hard is increased predictive capacity and decreased surprise. Armed with the above knowledge, it is possible to do both be happy and be productive

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