If you want to connect more with people, ask better questions.

I found myself reflecting after an evening hanging out with a friend. We chatted for hours about each other's lives. And yet I still had this sense that I wanted to know more, that we weren't connecting at the level I was craving. Now I'll couch this -- this feeling could be some neurosis of never doing enough or being hard on myself by habit. Regardless, the question of how to steward connection became more interesting to me.

Let's think of the lifecycle of a connection. We can break it up into 3 phases: pre-connection, the connection event, and post-connection.

The first phase is where we can set up our intention and/or goal for the connection. An okay intention may be that we want to get to know the person more. A better intention would be to ask them questions about something specific and go deep into that subject. Yet other good general intentions could be to make someone laugh, to be fully present, to be of service. A goal, as distinct from a general intention that guides us, is an objective such as inviting someone to a subsequent event, asking if the person will join your organization, or offering someone your help. Coming into a connection event with some guiding sense of where you'd like the conversation to go is perhaps the most important step as it brings us awareness of what we and our souls want. That awareness can then become a guiding force to direct our conversations and actions to where we want to be.

The second phase is actually being with someone else -- the connection event. This is the execution phase, where we have to turn our awareness into action. When the conversation starts going in a direction out of alignment with how we want to connect, we can gently move it back to our intention or goal. We can lovingly and enthusiastically insist on getting to know someone in a specific area of their life. We have to summon the bravery to take the wheel and direct the conversation; otherwise, the winds of convenience will steer the ship wherever. Going with the flow may be pleasant, and it's certainly the status quo for conversations -- nothing wrong or morally objectionable. But when I think of how I want to uplevel a relationship, bringing awareness to what I want and how to actualize it in connection is key to getting deeper with my connections.

The third phase is reflection. This post is essentially that -- a reflection on how things went, an addressing of a discomfort or dissatisfaction I feel in a connection, and the subsequent musing of how to use dissatisfaction as a compass for how to course-correct into more fulfilling connections. My reflection for the hang I mentioned above was to ask better questions, and I've had the thought to compose a series of questions that I can refer to when I want to connect more deeply with new and old friends.

Questions can be split up into several categories -- conversation starters, topic deepeners, clarifiers, and more.

I wrote down a few and also asked ChatGPT for some inspiration.

Conversation starters:

- What is something you are proud of that you don't get to talk about often?
- What is the most recent thing that you were a beginner at?
- What's a hobby or interest you have that might surprise people?
- If you could have dinner with anyone, living or dead, who would it be and why?
- What’s a recent book, movie, or show that you really enjoyed?

Deepeners:

- How did that make you feel?
- Tell me more (technically not a question but still in the spirit of deepening)
- Why do you think that is important to you?
- What was the most challenging part of that experience?
- How has that experience changed you?

Clarifiers:

- What do you mean?
- Can you give me an example?
- Why do you feel that way?
- What happened next?
- How do you see this playing out in the future?