I have been helping a friend and ministry colleague plan a series of conversations and workshops recently. As part of this experience, we have been sharing questions with others that we hope to help open the conversation and “break the ice.” Among these questions, we have landed on three in particular that we have found to be helpful.

1) If time or money weren’t an issue, what is your dream?

This is usually our first question. This helps people leave a little bit of reality behind for a moment, and to transcend any real or imagined barriers that they may have. Answers to this question that I have heard have ranged from being able to feed all of the world’s hungry to being able to always be on vacation on a private yacht traveling the world and experiencing its many diverse cultures. I don’t value this question as a barometer for character. I value it really as a way to break the ice and to open a door to conversations and visioning about what is possible when you open yourself up beyond just yourself and your preconceived notions.

2) What part of the purpose, vision, mission and/or values of the organization(s) you are part of connects most with you and why?

Whatever you are a part of, you are in fact a part of a team or group. Why are you part of it? For a paycheck? That’s fair, but my guess is that there is some deeper purpose or resonance with the team or group you are part of that connects with you. What is it? Why does it connect with you? This sort of reflection can be amazingly eye-opening both for yourself as an individual and leader, but also for your peers, colleagues and organization. In a sense, this may well point to the “why do you do what you do” piece and question I often like to highlight and have people ponder together.

3) What is the dream for your organization?

This is as open-ended as it sounds. In its best use case though, this is the vision-casting question. It provides an opportunity for the individual to share their ideas and dreams, and then if done in concert with others, the chance to collectively hear each other's dreams and ideas. From here, communal discernment and discovery can happen.

How would you answer these three questions based on where you are in your life’s work and context(s)?

Writer’s note: Most recently, the organization where these questions have been asked have been to people and leaders in specific churches & faith communities. However, I believe these questions would work for most contexts and situations. (For faith communities, I also like to add the question, “What might God be up to around here?”) 

One more bonus question: For whom (or what) does your heart break for?

If you’re itching for a little more vocational discernment or self-discovery, this question can really begin to unpack what areas you are passionate about in terms of serving, or in terms of meeting the needs of the world/community of which you are a part of.

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This post first appeared on Timothy's own blog.