The Pain of Leading

Navigating the Middle-Scale Trap

Sarah Chen on why fifty-person companies are harder to run than five-hundred-person ones.

Sarah Chen has built two companies through the band she calls the middle scale: too large to run on relationships, too small to run on process.

"At fifty people you have all the coordination cost of a real company and none of the machinery," she says. "Everyone is still waiting for the founder to be the routing layer, and the founder is the bottleneck they are complaining about."

We spoke for two hours about hiring ahead of pain, the specific meetings she deletes first, and why she now writes the operating manual before the headcount plan.

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