You may want to consider the possibility that the poor hit rate could be a cause not of your inferior hiring skills, but due to the fact that you are looking fo

You may want to consider the possibility that the poor hit rate could be a cause not of your inferior hiring skills, but due to the fact that you are looking for a rare combination of skills, for a job that doesn't sound very appealing: You want someone who's technically solid, while also good at understanding problems as described by laypeople, and doing all that without understanding the business domain. Way before Chesterton's Fence, you're looking for someone who is very good at communicating human-to-human, human-to-abstract and abstract-to-software. Tons of people can do one of the three. Lots of people can do two out of three. Three out of three is rare. That is not a "maintainer". So a different way to approach your hiring would be to revisit the process. If you were able to direct the conversations with the business side to a person who's good at linking between them and what needs to be solved, your maintainer could be just that - a maintainer who goes through a bunch of fixes in that ugly code base.