TWH Conversation Starters
Part of the healing journey is reflection, discussion, and seeding deeper connections. These cards can help you connect and have meaningful discussions with family, friends, coworkers and neighbors. Try to let your guard down and share your authentic experiences. Actively listen, understand, and connect with one another as we each move forward in our journey.
How it works: Each person picks a question for the group, and everyone answers. The themes are: Chicago Connections, Race & Identity, and Healing & Repair.
- Round 1 - Warm-Up: Lighter questions to open up the conversation.
- Round 2 - Real Talk: Tougher questions asking you to be honest and vulnerable.
- Round 3 - Cool Down: Reflective questions for you to share hopes for the future.
Instructions: Create community norms. Determine ground rules by asking: What do we all need to feel safe and respected? What does respectful discussion look, sound and feel like? Brainstorm together, write down rules, and commit to them. Helpful rules to include are: be present, listen, assume best intentions & honor confidentiality. If a rule is broken, address it directly, reaffirming the rule and its importance.
Round 1: Pick two warm-up cards / Round 2: Pick three real talk cards (at least one card from each theme) / Round 3: Pick one cool down card.
Don't forget to SHARE your conversation on the TWH Healing Map!
What is your favorite Chicago memory?
When you think about your culture and/or your ancestors, what are you most proud of?
What does healing mean to you?
Describe a positive experience you've had involving race, diversity, or equity.
How do you prepare yourself for difficult conversations?
What is your favorite thing to do in Chicago?
How often and where do you think about race (school, work, with friends, etc.)?
Which three places in Chicago should everybody visit?
What does it mean to be accountable to someone? To whom are you accountable?
What songs would you include on a Chicago soundtrack and why?
Pick three things you believe are required in any good and authentic relationship.
Name one person of a different race that you really admire. Why?
What is one routine you've started during the pandemic? What is one you've stopped?
Create your own warm-up question and discuss.
Describe a time you repaired a broken relationship.
Describe how you felt the last time someone caused you harm and the last time you caused harm.
What stereotypes do other Chicagoans have about your neighborhood?
When was the first time you were aware of your race? How did you feel?
Share a time when you experienced (or witnessed) racial profiling?
What is one thing you or your loved ones are healing from?
What did you learn about race in school? Do you think you should have been taught more?
What is the hardest part about living in Chicago?
What did you think about the protests this summer following George Floyd's murder?
Create your own real talk question and discuss.
Is Chicago a place that is welcoming to all? Why or why not?
Share a time when you had to grapple with a difficult truth from your past?
If you could "undo" one harm that was created in Chicago, what would it be?
What do you think is the root cause of violence in our communities?
What parts of your identity have most impacted your life (e.g. race, gender, class, sexuality, etc.)? What advantages/disadvantages have you experienced?
How do you process trauma and grief?
When you walk outside, how does your community look compared to other Chicago neighborhoods?
How do you think a community should address harm that has happened in the past? What if that harm is still happening?
How would the events of 2020 have impacted you differently if you were a different race?
What has been the hardest thing you have ever had to apologize for? Why?
Do you think true racial equity is possible in your lifetime? Why or why not?
What would you like to see Chicago do to promote racial healing?
Imagine writing a letter to future generations about 2020. What would you say?
What is your healing message for Chicago?
What would you do if you became Mayor of Chicago or Alderman of your ward?
Share a time when you truly felt free. How can you recreate that experience?
What is one thing YOU can do to address racism? What is one thing the City of Chicago can do?
If you could come up with a new nickname for Chicago, what would it be and why?
What lesson(s) do you hope we can learn together from the civil unrest of 2020?
In five years, what do you want Chicago to be most known for?
How can we support one another as we embark on a collective healing journey?
How can you challenge false narratives about yourself, your identity group, or others?
Create your own cool down question and discuss.
What does a fair and just Chicago for all races look like?
What is one thing you will do to move from conversation to action?