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The outsourcing that failed was development. A contractor with other clients gave him one or two days a week, and an outage once left a provisioning system down for 20 hours because he could not reach the guy. If you outsource engineering, hold your own code and servers.
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Four questions he asks before handing anything off: → Is the scope clearly defined? → Should this be a core competency at your size? → What does it cost either way? → How will you monitor the work? Watch the full talk ▶️ youtu.be/GBTw6WRlKvI