How a single conversation with my boss changed my view on delegation and failure
Margaret Gould Stewart

Margaret, this is a great story and message. Thanks for writing it.

Overall, I think your message is very true. One of the keys to it working well, though, is a manager’s sense of risk. As managers we have to let teams and projects have some risk, but we also have to have a decent sense of what the repercussions will be if a project goes sideways. Some failures are totally ok, but others are quite calamitous.

In my years in software management, I’ve usually seen micromanaging due to overreaction to previous failures, or due to organizational climates that severely penalize mistakes (e.g. Microsoft stack ranking in the past). A friend who worked in the Digital Corp recounted that government divisions get mired in red tape due to accumulated reactions to previous mistakes. It’s important for organizations to think rationally about mistakes and risk and how to have the right balance. One way managers can help teams is by asking them to think about risks and mitigations, and then let the team answer the question and solve the problems.

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