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With outsourcing, it helps a lot to break things down into small steps - it cuts out a lot of the risk upfront if you can build a complete "Hello World" early on, for example. You'll find out right away if the contractor can program, deal with version control, build automated processes, etc.

And this is where it helps if the client is a developer. A developer who understand agile processes should be well placed to break tasks down into vertical slices in this way.

On a related note, I highly recommend Trello for co-ordinating with remote workers. I just invite them to a board and send a "welcome" notification to them from a special "Message Card". They immediately get how the whole thing works even if they've never seen Trello or Kanban before, and you can spend most of the time co-ordinating on tasks by messaging on their cards. This is from my experience with researchers/admins and I'm planning on the same for working with a developer.

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