Sometime it helps to do reverse planning i.e. start at the deadline and plan your way backwards.
Ask yourself “In order to have the initiative executed in e.g. 6 months from now, what do I need to achieve as the last milestone and how much time do I need to complete that milestone?”. If the answer is “1 month”, then the last milestone should be launched in 5 months from now.
Repeat the process until you have identified due dates of all milestones that you need.
This method will typically result in more realistic planning and help you deliver on expectations.
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