This is a really good article over at 99U on overcoming the biggest obstacle to delegation. I love out how it starts out by nailing the exact difficulty that I find with delegation:
You’ve tried every productivity hack in the book and have reached your max capacity in terms of output. You know that you need outside help to bring the work to the next level… but you hesitate. On the one hand, the idea of not having to do everything yourself really appeals to you. On the other, you wonder if you can handle the management responsibilities on top of your already heavy workload.
Your concerns are valid. In order for people to help you, they need to know what you need and to receive feedback and direction along the way. Your workflow that was uniquely yours will now have to account for another person. With the right systems and communication, this process can run relatively smoothly. But without them, the people who were supposed to help can end up creating more work.
She then gives five very helpful strategies. It’s worth the read.