I have heard a number of calls this summer for the need to “get comfortable with being uncomfortable” in terms of talking about racism, effects of racism, police violence, polarizing politics, and more. I agree that it is important to have these, and I also think it is important to prepare for them. Fortunately, there are many resources available to help with having those conversations.
This is a good Ted Talk to set the foundation: 3 Steps to Having Difficult Conversations: https://ideas.ted.com/3-steps-to-having-difficult-but-necessary-conversations
I have shown this before in class with college students, but it would also be appropriate for community settings and high school students as well. From this Ted Talk you can go into establishing some boundaries and expectations for your own uncomfortable conversation. The Center for Research on Teaching and Learning at the University of Michigan has some great guidelines for discussing difficult and “high stakes” topics that I have also used a number of times, and they are also relevant to helping people prepare for leading these kinds of conversations in multiple settings (faith communities, classrooms, K-12 school meetings): http://crlt.umich.edu/publinks/generalguidelines Teaching Tolerance has a curriculum for having difficult conversations that is built for K-12 settings, but can also be adapted easily for use in higher education and community settings http://www.tolerance.org/sites/default/files/general/TT%20Difficult%20Conversations%20web.pdf
As an added bonus, Emmanuel Acho has developed a collection of videos called Uncomfortable Conversations with a Black Man. These are videos that can be useful for families to watch together, they could be used in classrooms, they are a tool for you to watch and reflect on personally and then discuss with someone. You can learn more about this work, his upcoming book, and see the videos here: https://uncomfortableconvos.com/ I especially have valued the one addressing race and religion (episode 7), as well as the one about helping parents to raise children to see color (episode 3). The videos are one way to start your own conversation in your own community, whether that is your family, your faith community, or your community of learners.