James Bond: Do you expect me to talk? |– Goldfinger (1964)
Auric Goldfinger: No, Mr. Bond, I expect you to die
You’re looking to dig deeper right? you’re looking to understand more about the product, the solution, the market, the audience, the ecosystem, the vision, and much more to try walking in their shoes and understand how to approach and explain their value forward.
You will likely get the answers if you keep asking questions, but you will get more insights, anecdotes, stories, reasoning, and personal experiences if you actually talk to them and have an open conversation.
Just think about yourself and how defensive you may get when being questioned, and how open you become when an individual is having a conversation with you, listening to you, showing interest in you, and waiting for your answers rather than planning the next question.
Besides getting the answers you seek, you want to uncover hidden gems, find new points of interest that could lead to new avenues, ways, words, and phrases which you may not be aware of, and simply let the founders reveal the real pains.
When you’re just asking questions, founders already have pre-prepared answers, which may be sufficient, but we’re not looking for just enough, we’re looking for gold.
To get them actually talking, you need to be a great listener; and to be a good listener it needs to be a conversation and not an interrogation.
So talk to them, listen to them, and care about finding out the pains they alleviate, the value they provide, and the possible hidden passion.