Delegation is most definitely not an easy task. That's because knowing what to do and how to do it are two completely different things. Delegation is an art, not a science. Delegation is subjective, open-ended, and can be very emotional. Unfortunately, many owners, managers, and workers do a very poor job of delegating. Here's three decent reads on understanding the pitfalls and improving delegation skills: The Art of Delegation: 11 Ways to Work Smarter Today; How You Can Become a Better Delegator; and The Triple Whammy of Poor Delegation.
A main reason delegating is so difficult is that in many ways it boils down to having good communication skills. Thoroughly knowing the staff's skill sets, limitations, current workload, desire for additional responsibility, and level of direction needed are all critical in order to delegate effectively. Also, a manger's ability to effectively communicate what is needed depends on how well they know their employees. Not easy.
In addition, there's a 'letting go' aspect that managers need to overcome in order to delegate at all, never mind trying to do it effectively. Not easy. Many managers fall into the trap of 'I can do it better/quicker myself' or 'I'll have to spend time reviewing it anyway.' If you don't trust your people to do what they are capable of doing, eventually, you will simply burn yourself out.
Lastly, managers need to fight the urge to micro-manage when they delegate. Not easy. There's a fine line between giving proper direction, expectation, and explanation of a task vs. telling someone exactly how a task should be done. One of the points in the Art of Delegation article is that different isn't wrong. Too many managers simply don't get this.
Delegating is a critical management soft skill for owners and managers. It's definitely not easy, which is why it's no surprise when many of them fail and become the bad boss who has no clue.
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