To set an achievable milestone, have a clear deliverables criterion, you need to have a deep dive analysis, especially form the stakeholders. You must keep away from not communicating truly with the those who in the end execute the initiative. Stakeholder evaluation means figuring out who the change will have an effect on, how it's going to have an effect on them and the way intensely the initiative will adjust their work lives.
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What you need to know about leading people through periods of learning and uncertainty, understanding why some people resist change and how to manage it.
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