How can we set up guardrails to make our calculations more accurate and objective?

Here are my quick five questions to assess how complex any given initiative will be:

1. Is the challenge one-and-done? Or will many iterations be required before the challenges (and potential solutions) are optimized ? How many?
2. Can the current team do it quickly and easily? Do you need external supports?
3. How many people have to be managed? How experienced are they?
4. Does it happen on a cyclical basis?
5. If the current leadership changes, will the next leaders be able to quickly pick it up?

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