Freedom works for the people who were hired for it

The advice reverses a common instinct. Founders who hire someone talented often keep checking their work, which wastes the talent and teaches the new hire to wait for approval. Andrew Mason’s line says the hard part is the hiring. Once the right person is in the seat, the job is to get out of the way.

For a small company this is close to a law. A team of twenty cannot afford layers of review, and people who are good at what they do produce their best work when they choose how to do it. Groupon’s early writing staff, known for an odd, jokey voice in the daily deal emails, is a fair example. The voice came from writers given room to be strange, and it set the company apart from the imitators that followed.

The trouble is the first half of the sentence at speed. Groupon has gone from a handful of people in late 2008 to thousands of employees across dozens of countries, many of them sales staff hired in a rush. At that pace nobody can promise every hire is great, and freedom given to someone who is not yet good at the job, or who does not share the company’s standards, produces inconsistent work and mistakes that land on customers.

Freedom also has to include room to fail in small ways. A manager who grants autonomy and then punishes the first mistake has granted nothing, and the team learns that quickly. Companies that make the formula work tend to say plainly which decisions belong to the individual and which need a second opinion, so people know where the edges are.

So freedom at scale needs structure around it: clear goals, a few firm rules, and managers who can tell strong people from struggling ones quickly. The line holds for the people it describes. The real work is keeping the proportion of them high as a company grows.