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Where Do You Begin?

  • Writer: Tim Maloney
    Tim Maloney
  • Apr 21
  • 1 min read

Some of the most successful plans I've been part of were not the most detailed ones. And sadly, a significant number of the most complex ones never got off the ground.

A plan nobody can execute isn't a plan. It's a document.

So how to overcome this? How do you filter out the noise from the critical? Most times, the hardest question is: where do you begin?

I use five stage-zero questions before any planning work begins. Not in the middle of the process. Before it. An implementable strategy will always outperform an all-encompassing plan that collapses under its own weight.

1. What's the goal? Plain language. No jargon. Alignment starts here, not after the plan is built.

2. Define success. Close your eyes for a moment. What does success look like, sound like, and feel like when we get there? The goal tells you the direction. This question turns that direction into a shared picture.

3. How will you measure it? A number. A metric. A specific data point. People often agree on the destination but disagree on arrival. Resolve that now.

4. What are the resources and constraints? What do you have to work with, and what won't move? A plan built without knowing the constraints isn't a plan. It's an assumption waiting to be corrected at the worst possible moment.

5. What's the timeframe? Timeframe shapes everything. What's realistic, what gets prioritized, and what gets cut.

And the last critical part: all of this must be documented, or it isn't real. Once those five answers are clear, the real planning work can begin. Not before.

 
 
 

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