…but how often do they actually get clear?
Instead of pitching, try shifting the conversation with a few better questions:
“What assumptions are you making that, if wrong, would change the deal?”
“How did you arrive at those rehab or build numbers?”
“What does this look like if timelines stretch 60–90 days?”
“Where have you seen this type of deal go sideways before?”
“What’s the exit if your first plan doesn’t work?”
Not to challenge someone…
But to understand what’s really there.
Because most deals don’t fail from lack of opportunity,
They fail from untested assumptions.
And most investors don’t need more deals…
They need better clarity on the ones already in front of them.
The interesting part?
When you ask questions like this, one of two things happens:
Either the deal gets stronger…
Or the truth shows up.
Both are valuable.
Curious how others approach this,
What’s a question you’ve asked that completely changed how you saw a deal?