Sometimes it’s as simple as asking someone:
“What is it you’re trying to make happen?”
‘yada yada yada’
Beware the yada. Did they answer you clearly? After working with 400+ companies, I’m no longer surprised by how many lack a clear vision of what it is, specifically, they’re trying to do.
You really can’t proceed with planning until you’ve got a consensus answer to that first crucial question.
I often use a treasure map metaphor.
Draw out an island. Put a little ‘x’ and a big ‘x’ on there. The little ‘x’ is where they are today. The big ‘x’ is where they want to be.
Start by asking them to describe what the big ‘x’ looks and feels like. Then ask them to describe the little ‘x’ – where they are today.
Then draw a dotted line between the two and ask them how long it’s going to take us to get from one to the other.
Once they answer that question – ask them – “Why aren’t you there already? What’s in your way?”
Then, after everything, ask them simply … “what do you think is the first step?”
You can guess what’s next.