Does Your Startup Feel Chaotic? Good.

Kate here. No one goes into a startup thinking that there won’t be some amount of chaos—myself included. Today we’re thrilled to publish a new piece about startup chaos by Jean Hsu, whose post about ask vs. guess culture hit number one on Hacker News. Jean is a vice president of engineering with whom I had the opportunity to work at Medium, where she was an early engineer. She’s been writing about startups for a decade and founded a coaching and leadership development company for engineering leaders. In this piece, she distinguishes between the good startup chaos—what she calls necessary chaos—and the bad—or unnecessary—and offers advice on how to reduce the latter.

Startups are inherently chaotic. There are a lot of unknowns, and teams need to navigate uncertainty as startups grow. New data might require you to re-order your roadmap, or you may fail several times as you experiment to find product-market fit. Sometimes, you’ll need to pivot your product to respond to a change in the market. In more extreme cases, you’ll need to pivot your entire company strategy.

Some of this chaos is good. It leaves room for creativity, gives team members more agency, and keeps your organization flexible. I call this necessary chaos. 

What doesn’t work is unnecessary chaos, borne by a lack of planning. Unnecessary chaos eats into any bandwidth for necessary chaos, which is the lifeblood of startups.

To be clear, no startup is completely without unnecessary chaos, and the gray area between unnecessary and necessary chaos is wide. However, in my experience as a vice president of engineering at several early-stage startups, I know firsthand the importance of not giving in completely to unnecessary chaos.

In this piece, I lay out methods for startups to identify unnecessary chaos, learn how to manage and reduce it, and make room to take on necessary chaos.

Unnecessary versus necessary chaos

In my 13 years working at startups, I’ve witnessed many examples of unnecessary chaos—here are a few.

A major release has been planned for months, but launch communications—new positioning, website copy, customer email, blog post—are reviewed at the last minute.

A manager reschedules 1:1s every week because of ongoing conflicts, and they don’t take the time to find a recurring slot that works.

There are meetings with no agenda or structure, and there are often follow-up meetings.

CEOs artificially manufacture deadlines, fire drills, and strategy pivots to force execution on their team. They don’t always provide new information or context as to why. Sometimes, these pivots lead to frequent reorganizations that break apart effective teams. A red flag is when a recent hire goes through multiple teams and managers within a year at the company.

Although there have been ample opportunities to provide feedback, someone swoops into a design file as a feature is about to launch, questioning its basic premise and functionality.