Use Analogies and Parallels
Use parallels that are meaningful to the person to frame your point around their values and their own history. Use examples from their own life - things that have happened to them - or events and phenomena you know they relate to or understand. For example, while many white people have found reasons to decry Black Lives Matter protesters as vandals and rioters, they celebrate American Revolutionary protesters/vandals like the perpetrators of the Boston Tea Party. In a conversation about black protest, bring up the Boston Tea Party and ask how the two are different. Their answer to that question will provide an opening for further discussion.
It’s also sometimes helpful to just use hypothetical analogies to get the person to see things from a different perspective or to universalize a tricky concept. For example, this parallel can help explain that historical context is the reason racist jokes aren’t funny: “What if your friend had just been in traumatic car accident? Would it be funny to play a prank on them where you pretended to hit them with your car? No, because of the context of your friend’s accident. The context of slavery, racist laws and the long history of racism in our country is the context we live in - that’s what makes racist jokes not okay. We can't pretend the past didn't happen.”