Companies, Small & Large

People often ask me what it's like to join a larger company versus a startup. In truth, every business is a world unto itself with unique challenges and opportunities, but I've noticed a few common patterns I'd like to share.

In the past few years, I've worked as an engineer in a variety of different sized teams. Straight out of college, I began at a mid-sized startup, then I moved to a company ten times the size, and more recently, I've turned a few side projects into businesses with friends.

There are some obvious differences among companies and teams of different sizes: Larger companies tend to have more hierarchy and specialization among roles, along with better benefits (salary, equity, 401k matching). But these differences aren't particularly surprising and certainly aren't universal. The important difference I've discovered is this: As an employee of a large organization, it is an impossible task to understand the entire product and business—let alone the entire organization of people responsible for producing it.

This happens for two main reasons. The first reason is intuitive: At a large company, you're already showing up late to the party, so you're at an informational disadvantage from the start. Important decisions have been made for reasons that no one can remember, and there's a history that spans years or decades. And to be honest, it won't matter that much. Your job, in all likelihood, will not be to make the same products again or solve the same problems, but rather to conceive and build the Next Thing. Put another way: Whenever you join a company—especially a growing one—you're actually joining the company that it is going to become.

The second reason is what I'll call the bridge painter's problem. According to urban lore, the Golden Gate Bridge is so large that painting it is a constant, year-round endeavor; as soon as they've finished painting it from one end to the other, it's time to begin painting again from the beginning. Such is the nature of corporate life. Organizations are constantly shifting and transforming in subtle ways every day, accruing additional complexity as priorities shift, project ownership changes hands, and long-term contributors leave or retire. By the time you've familiarized yourself with everything, your knowledge will be outdated.

This problem isn't unique to companies; it's a symptom of our bounded capacity for information processing. According to Dunbar's number, there's a natural limit to the number of friends you can have—150 to be precise. Social media has certainly expanded our capacity for reaching and communicating with larger numbers of people, but you can only really know about 150 people (or so the theory goes). Once a company reaches this size, all sorts of things start to break down. It's no longer efficient to relate information through people alone because no one knows each other. You start to need tools and frameworks and, ironically, even more people to mediate information from one group to another.

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