Help—my company is complete chaos!

I've spent the last 12 years of my professional life mainly working in startups.

I worked at a startup that grew from a couple hundred people to several thousand, becoming a multi-billion dollar company. I've worked at startups that have gone bankrupt. And I've co-founded a moderately successful startup. Every single one of those companies were crazy places to work most of the time.

If you have ever worked at a startup yourself, or known someone who has worked at a startup, you know that my startup experience is typical. Life at a startup is chaotic a good part of the time.

But they are chaotic for a very explainable reason: startups are biased towards taking action.

They have that bias out of necessity. Most startups don't have a predictable revenue stream yet, so they are driven to proactively work to find one. Their entire purpose is to figure out what their revenue stream will be. This is in contrast to established companies, who are primarily concerned with maintaining and growing their existing revenue streams. A startup doesn't have a predictable revenue stream, so it has to be biased toward action.

It's this bias towards action that means startups need to be chaotic.

That groups solve problems better than individuals is such a common observation that our language is full of cliches on the topic: "Two heads are better than one," and "There's no 'I' in 'team,'" and "the whole is greater than the sum of its parts."

Teams do solve problems better than groups, and it's because of the positive effect each individual can have on the rest of the group.

In his book Rationality, cognitive psychologist and author Stephen Pinker points out that groups make better decisions than individuals because the members of the group can discover mistakes made by the other members. As individuals, we are often blind to mistakes in our own logic. It is much easier to see another person's mistakes than our own.1

When we work together in a group, we quickly find each other's mistakes, correct them, and perform better.

There's another word for finding problems in another person's work and talking about it: feedback.

Feedback helps correct errors. Feedback also makes problems visible. So when there's a lot of feedback going around an organization, all the problems of an organization are visible to everyone.

Organizations with a good feedback culture will have lots of visible problems. Some people might describe the organizations like this as chaotic... and they are!

But, to be clear, every organization has problems. If there are no visible problems, that doesn't mean the issues aren't there. They are just hidden! And they are hidden by a lack of feedback.

In theory, a smooth and seamless organization is a good ideal to strive for.

A perfect, smoothly operating organization seems like a utopia where every piece of the puzzle fits perfectly, and everything runs like clockwork. But this utopian view is deceptive. In reality, an organization that appears flawless is probably suffering from a dangerous lack of feedback.

In an "orderly" organization, problems and mistakes may remain undetected and uncorrected, gradually accumulating hidden issues. On the surface, everything may seem calm and orderly, but beneath this serene exterior are silent threats that could potentially lead to significant crises.

In contrast, a chaotic organization with many visible problems could be a sign of health. It indicates that mistakes are being identified, shared, and (hopefully) corrected.

Let's look at the example of two societies: autocratic regimes on one side, and liberal democracies on the other.

On the surface, autocracies, with their centralized power and controlled media, seem to be well-ordered societies. However, the lack of feedback mechanisms and suppression of dissenting voices means that problems are hidden and unaddressed, making them potentially brittle.

On the other hand, liberal democracies, with their cacophony of voices, divergent views, and public criticism of leadership, may appear chaotic. 

Yet, this "chaos" allows for constantly discovering and rectifying mistakes. It provides resilience to these societies as they can adapt and evolve in response to issues that arise.

"A healthy society ... allows information sensed and contributed by its members to feedback and affect how the society is governed."

— Steven Pinker2

It's counterintuitive to think that chaos could be a sign of strength.

Yet it's the ability to acknowledge mistakes, to give and receive feedback, and to adapt that ensures the health and success of organizations and societies.

It would be better if we all recognized chaos as the indication of a learning and evolving entity. And instead of looking at it as a weakness, we saw it as the strength it actually is.