A Founder’s Guide to Sales Meetings

1) Would this work in an environment like yours?

This is a closed question that gets the receiver to quickly evaluate whether there is a fit, side-stepping the question of price.

2) How would this work in an environment like yours?

This is an open, leading question that gets the receiver to simulate the product in their organisation.

The second is more useful if the prospect is showing strong signs of interest, but can be perceived as coersive if the prospect is still on the fence (in which case the first version may be better).