What are the best questions to ask, to get to know someone at a profound level?

I can help you get to know someone at the profoundest level possible with an introductory meeting :). Lets acknowledge that getting to know someone at a truly profound level takes time because people are difficult to know. There is layers and layers of defense mechanisms specifically designed to steer you the wrong way. With that caveat out of the way, here is a strategy to get deep as quickly as possible.

You cannot get to know anyone without their permission. So you need them to say yes to opening up.

If you want to get to know someone, your objective is to get them comfortable. Get them to lower their defense and open up to you. You do this by being non-threatening. Asking questions can be helpful, but it can also get people to raise their defense. That is because, in unskilled hands, asking questions can feel like an interrogation.

I think the key, at least at first, is not so much the questioning skills, but an attitude of acceptance, non-judgement and open non-verbal signals.

What does that mean? It means you are open. You are not folding your arms, or looking at them in a harsh judgemental way. You are smiling, being gentle, matching their tone and voice speed, and mirroring their behavior. You are communicating one thing: You can take off the mask you wear and trust me with who you really are - I won't judge or hurt you.

To do this, it is 80% everything but your words. You communicate that by how you stand, how you hold your gaze, how you smile, how you hold your body, how you touch someone, the tone of your voice, the melodic element of your tone, how encouraging you are as they speak, how interested you seem to them, etc. It is not about words but it is about everything else. The other 20% is questions. But questions is used to give the conversation direction. It is not necessarily about getting to know the person, but getting to know specific aspects. How do you get to know the person? It is the response to the question. If you ask them "how was your vacation?" and they tell you "Vacation was OK. I was just busy doing a lot of work". That may mean they are not that interested in talking about the vacation but they do want to discuss their work. You let them lead and unload the burden of their heart. Don't push a specific agenda. Ask your questions, but pay attention to "free information" or "extra information" that is unrelated to the question to give you a clue about the direction they want to go.

There will be a point where you feel the energy of trust. you sense that the person trusts you and are willing to peel of the masks we all put on to play a "part" we are required to play and are willing to show you their "real" self. Isn't that the best feeling in a relationship? To feel accepted and trusted? The speaker feels accepted and the listener feels trusted?

Once this happens, the floodgates open. You ask questions, they ask questions, it is a free flow of conversation. You are in a zone. Nothing feels forced - it feels natural, easy, elegant, seamless.

They will open themselves and let you know their fears, their dreams, their values and beliefs. You will do the same. Because that's what it feels like to be in a trusting place - you both share fearlessly.

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