• When you reach a point in your business where you are juggling too many balls and you begin to drop them.
• When you want to free yourself of work in areas that do not align with your strengths or which you do not enjoy.
• When you want to free up your time to do money-making tasks [i.e., business development].
• When you need to create free time to work on your business [i.e., strategic work]. 
• When you want to reduce the amount of time you work [i.e., more free time].
• When you want to leverage talents and create growth in your company.
• When you want to ensure task back-up [for example, to protect the company and cover illness, etc.].
• When you want to prepare your business for your exit strategy [i.e., succession planning].
• When you want to reduce your stress level.

• With the overall corporate best interest in mind - who is best skilled at doing the task?
• Considering “bang for buck”: particularly, the impact on your key corporate goals - who is best skilled at doing the task?
• Considering past practice involving similar tasks - who is best skilled at doing the task?
• Considering your track record of delegating tasks - have you illustrated good practice? Good Habits? Bad Habits?

NOTE: in delegation of business tasks, one man’s trash isn’t generally another man’s treasure.

Rule of Thumb: good leaders do not assign tasks they have not performed or would not perform themselves.

Rule of Thumb [corollary]: leaders rarely assign unique tasks…so…Is this task unique? [If it is - step back and measure twice before you cut the wood.]

Consider employee’s [business savvy] growth and development…are you training the person for the future? [Or, are you simply downloading stress?]

Consider fairness: what amount of workload is already on the recipient employee’s plate, other staffs’ plates, and your plate?

Consider job-content satisfaction: are you providing your people the opportunity to perform diverse, interesting tasks? [Or, are you piling up repetitive, tedious, non-challenging tasks?]

Delegation; you have much to think about if you want to do it right!