Insight and Empathy
It's easier to sell when you know a client's desired outcome and the obstacles they face. You might ask questions like:
What would success look like for you?
What about your organisation keeps you awake at night?
But these questions lack something. They're not offering value. They're one-way traffic. They're making clients do all the work.
Much better a conversational lead, something like these examples:
You may like to know what success looked like for our client Acme. Three key results came from their transformation work ... (offer some valuable insight, then ask your question with respect) ... May I ask, with your project, what results are you looking for?
Before projects like these CIOs tell me they have some massive challenges which keep them up at night, things like ... (offer more valuable insights, then ask your question with respect) ... do those obstacles resonate with your experience here?
This way of asking questions allows you to add insight and gives you a chance to show empathy.
How are you adding value with the questions you want to ask?