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Don't take down a fence until you know why it was put up.
Have you ever joined a new team and wanted to immediately change seemingly unnecessary processes or code? Why is our banking system still written in COBOL? If a fence exists, it was probably put up for a reason.
Engineers are especially susceptible to tearing down Chesterton's Fence, simply because they have been so successful doing it for so long. Many processes could be immediately improved just by making them digital. But understanding why a fence was put up in the first place is always a good exercise to start with.
Larry Page famously fired all the product managers at Google in 2001. Why should engineers have to report to someone less technical? At first glance, not a terrible idea. How many of us have had non-technical product managers who fail to fundamentally understand a technical product? In practice, it was a decision that was quickly reversed.
Chesterton's fence is a concept that's closely related to the Lindy Effect – things that have been around longer tend to have a longer future life expectancy. These things are more likely to have an important underlying reason why they exist – and as a result of their longevity, that reason is often forgotten or not known to new generations.
For many things, I believe we have to figure them out ourselves from first principles. But Chesterton's fence gives us a good counterbalance to prematurely changing things that we don't immediately agree with.
In the matter of reforming things, as distinct from deforming them, there is one plain and simple principle; a principle which will probably be called a paradox. There exists in such a case a certain institution or law; let us say, for the sake of simplicity, a fence or gate erected across a road. The more modern type of reformer goes gaily up to it and says, 'I don't see the use of this; let us clear it away.' To which the more intelligent type of reformer will do well to answer: 'If you don't see the use of it, I certainly won't let you clear it away. Go away and think. Then, when you can come back and tell me that you do see the use of it, I may allow you to destroy it. – G.K. Chesterton (1929)