What you want to know

It’s kind of awkward.

You might sometimes feel like you’re in a lower position than the prospect.

You might think, “Who am I to ask these questions?”.

You feel awkward asking.

Especially hard questions. 

But, my friend, the ONLY way through is to ASK these questions. 

You need to ask.
The prospect needs to respond.
You let them explain.
They share their thoughts. 
You probe for clarity.
They clearly define their objections.

Asking questions, even difficult ones, is the only way you will clearly understand what the prospect is thinking (in regards to the sale).

Every time you meet/talk with the stakeholder, you should gather information to slowly piece together the puzzle.

Between the lines of these questions, you will be gaining micro-commitments. 

Discover by asking questions. 
Answers turn into micro-commitments. 
Micro-commitments can potentially get you the “yes” you have been waiting for.

Then it won’t feel awkward anymore…