Clarity before commitment

Here are four questions that will save you time and nerve when discussing any significant work:

Question Uncovers
Why are we doing this? Understanding the drivers behind the requested work helps you make a better decision. Is it here just because? Is it tied with a specific objective? Who is asking for it? Ask why several times if needed.
What is our intent? Clarify what are you hoping to achieve by completing this work. Consider tangible and intangible outcomes alike. Make it specific, not generic.
How will we do it? While clear destination and direction are important, execution still reigns supreme. Consider fastest routes. Do no harm. Work doesn't get done on its own—remember the 3 Ws: what, when, and by whom.
What needs to be true in order for us to succeed? Blind implementation is great way to waste resources and human potential. Always question underlying assumptions of the matter at hand. Trivial misunderstandings can easily lead to significant problems—which were entirely avoidable. Risk cannot be eliminated, but it sure can be mitigated.

Answering above is linear process only once—when you encounter the work/project/assignment for the first time.

From then on it's an iterative process that should be continuously happening as you keep learning more and more.

It's OK being wrong, as long as you course correct on time. Keep it simple; keep it light.