Examples of difficult questions might be:
Do you support docker?
When is LDAP going to be ready?
Can you do quarterly payments?
These questions can be uncomfortable perhaps because:
You personally might not know or understand the concept.
It isn’t clear to you when Iguana will support such things.
An immediate tool to handle such questions is to ask for more clarification - asking questions that help you understand why these questions matter. What will drop out will be understanding what these questions relate to in a larger context.
A larger context usually makes it possible to link the question to topics that we are already familiar with. Sometimes we refer to this as finding a higher frame, i.e.:
You should made a big fuss over my birthday and bought me jewelry!
is really about → I need to feel loved and taken care of.
Also, the benefit of clarification is that you are getting a better conversation which reveals more information that can give you better ideas on what is going on - what are the real problems which need to be solved?