Skills | How to Have a Difficult Conversation

I have been trying to put my thoughts to words for over a week now. I keep writing and rewriting and deleting and starting over. What do you say about all of this? Big picture, the world is a very different place compared to how it was sixty years ago, one hundred years ago, two hundred years ago . . . but in many ways, a lot of antiquated social structures, racism, and residual biases (whether explicit or implicit) still exist.

If you don’t think that’s true, take a closer look at the people in your life (parents, grandparents, coworkers, friends who live in a different city than yourself) and their stance on things like: interracial relationships, same-sex marriage, and women in leadership roles. There are people in this world (today) who staunchly believe some (or all) of these topics are not okay (for one reason or another) . . . and at one point in time, all three of these things were illegal in the United States. Mind-blowing, I know, but let me add a little context:

Most/all of these topics have to do with social (and/or religious) constructs that’ve been in place for centuries. I’m sure you could trace it all the way back to Greek and Roman civilizations (maybe even earlier?). There were different classes of people and that’s just how a society was organized. Fast-forward to America’s colonization and again, tiers of people based on occupation, income, and race. I should also note that racism is not unique to the United States. It can be found throughout history around the world, and in some places, it’s unfortunately still present. BUT, I can’t speak for the rest of the world . . . I can just talk about my own experiences as an American millennial woman.

I know I’m not alone when I say social media, the news, and other sources of information have felt overwhelming as of late. While some people have suddenly become experts on all things legal, political, and historical . . . others have felt cornered into silence for fear of saying the wrong thing (and worse than offending people, getting torn apart by keyboard warriors who don’t blink an eye when they incite violence for insensitive or ignorant rhetoric). There are some of us who feel like we need to unplug from the litany of updates and live videos, but at the same time we feel compelled to keep watching to stay informed and educated and to bring about change in our communities. Even the mention of “unplugging” can draw criticism, because some consider it a privilege to be able to do that in the first place. And then there are the people who don’t understand why so many are quite literally up in arms about a man named George Floyd, who died as a result of excessive force whilst in police custody in Minneapolis, Minnesota on Memorial Day weekend. I hope if you fall into any of these groups, especially the last one, that you keep reading.

In a way, it feels like you’re damned if you do, damned if you don’t. Post a black square to show you’re an ally . . . but if you don’t put the right caption, it’s performative activism without any backbone. Go out and protest, but don’t take a picture, because if you do, you’re capitalizing on a cause you don’t actually believe in or aren’t personally affected by. The list could go on, but my point is people will show up how they can with what they can, and the reality is you’re not going to please everyone. At the end of the day, all you can do is try and improve who you are as a person, one day at a time.

The internet is a wealth of information, and I hope more people continue to use it to do their own research before they blindly hit “repost.” Social media has created this echo chamber that makes us believe that the accounts we follow and interact with is representative of the outside world. It’s created a generation of “unfollow me if you don’t agree with me,” but the reality is that while you can unfollow people you don’t like on Instagram and mute relatives who piss you off on Facebook, you’re going to have a boss, a coworker, or someone else in your life that you don’t agree with (and can’t unfollow/mute/etc.), at some point in your life (whether it be about big social issues like this, or something else), and you’re going to have to figure out how to coexist. And how do you coexist?


Historically, BIPOC (Black, Indigenous, People of Color) voices have been marginalized, oppressed, or all together not included in discussions throughout our country’s history. Think about it. You probably read dozens of books during school growing up, but how many of them were written by a Black author? Maybe one? Did you know that the Lone Ranger was based on Bass Reeves, an African American law enforcement officer who was the first Black Deputy U.S. Marshal west of the Mississippi River? Did you know that the iconic Betty Boop cartoon done by Max Fleischer was actually a caricature of a Black jazz flapper by the name of Esther Jones, who was known for adding “boop oop a doop” to her vocals?

Two random facts, but nonetheless important, because both are surface-level pop culture icons associated with Caucasian origins, when in fact their inspirations were Black and hardly ever given reference or credit. This doesn’t even begin to scratch the surface, but if you’re curious to learn more on this topic, I’d encourage you to do some research into inventions, discoveries, and other historical moments that BIPOC have not been given proper (or any) credit for.

It’s all well and good to go out and protest in the streets and to post feverishly on social media every time you see a captivating graphic. But humor me this: if you’re one of those people who’s unfriended people you don’t agree with . . . aren’t those the people you need on your team in order to bring about meaningful, long-term change?

If you don’t care about reaching those people, you should probably “x” out of this post . . . but if you do think those close-minded people are worth a second chance . . . let me make a comparison about what’s going on right now to what happened one hundred years ago when the 19th Amendment passed. Women didn’t get the right to vote right away. It took nearly fifty years of state and local government advocacy until national women’s suffrage passed in 1920. It took countless parades and protests, upheaval and turmoil for it to happen. . . heck, there were even women who were against it because they claimed it was “dirty” and a “collapse of their morals.”

It’s wild to even fathom a period of time when women were so disproportionately unequal to men. Today, you’ll find women in nearly every faction of politics, not to mention in leadership positions of Fortune 500 companies, non-profits, and everything in-between. For millennials, Gen X, Y, and Z (or whatever the teenie boppers are called these days), it’s hard to imagine living in a world where women do not have the right to vote. One hundred years ago, women also couldn’t do the following:

-get divorced (South Carolina didn’t legalize it until 1949…)

-join the military (it wasn’t until WWII, when there was such a shortage of soldiers, they allowed women to enlist in non-combat positions)

-not be required to take your husband’s name upon marriage (Hawaii was the last state to rescind this law . . . in 1976)

-own property (until 1848, if you were married, you couldn’t own property . . . it legally belonged to your husband; this was slowly repealed state by state until 1900, but societally it was still taboo for a woman to own any kind of property until a few decades ago)

Now these are just a few things women have seen progress for in the last one hundred years. I haven’t even skimmed the surface of what BIPOC have endured. I dove into women’s history because I grew up with female relatives who did not have the right to vote. They were told at a young age that their career ambitions were limited to that of a teacher or a homemaker, but absolutely not both. They were ridiculed and ostracized if they went against the societal grain, and that’s exactly what’s happening right now. The status quo, age-old societal institutions that disproportionately disadvantage BIPOC are being called into question and PEOPLE ARE STARTING TO FEEL UNCOMFORTABLE.

Now, I’m not saying Black people need to convince White people that they’re deserving of anything. They’re humans who bleed red just like anyone else. End of story. Racism, when it boils down to it, is a question of human rights. There are visible inequalities in our society and in all honestly, it’s appalling it’s taken this long to make changes. I think a huge reason why it’s taken so long is because people aren’t holding themselves accountable and when faced with the choice to stick their head in the sand and ignore what’s going on . . . or choose to have a difficult conversation about race and discrimination and bias, they choose the former time and time again.

We, as a society, need to take responsibility for ourselves, first and foremost. You can’t shame someone into changing how they see the world. But by having difficult conversations with them, by continuing discussions off the gram, there’s a good chance that you can bring them around to seeing the world with more compassionate eyes.

Okay, so how do you have an uncomfortable conversation with someone? Aka, how do you sit in a room with your Grandpa and explain to him why you’re offended he’s posting “All Lives Matter” on his Facebook instead of “Black Lives Matter.”

And for the people in the back, yes, I have receipts for what I’m saying: I have three graduate degrees, two of which specialize in conflict resolution and I’ve mediated several hundred cases in the last few years. Most of the time the parties are 100% not in agreement with one another when they sit down at my table, but when they get up, they not only have a better understanding of the other party’s point of view, but very often they’re in agreement about whatever they were fighting about before.

So without further adieu, ten steps to help you facilitate a difficult conversation:

  1. Figure out what you want to get out of this interaction. If you’re trying to change their mind, you might need to rethink this. If you’re trying to have a respectful dialogue, keep reading.
  2. Go into this being open that you might hear things that make you uncomfortable. Not only is that okay, but it’s encouraged. It’s okay to take in new information. It’s okay if that new information changes how you feel about a situation (and vice versa for Grandpa). You shouldn’t be going into this to “convert” him, if you will, but change starts at a micro level. It starts with this first difficult conversation. Go into this knowing you could walk away from this experience more frustrated than you started and THAT IS OKAY.
  3. Know, going into this, it’s okay to take breaks. If things get too heavy or overwhelming, respectfully let the other person know you need to take a break, but give notice of when you’ll circle back (5 minutes, 10 minutes, etc.).
  4. On the topic of respect, try your best to be respectful of the other person. He is still going to be your Grandpa after this conversation. There’s no need for name calling or derogatory statements (from either side). I’d recommend one person talking first, the other stating their point (no interruptions), and then form a dialogue from there.
  5. Make a point to talk one at a time (don’t talk over the other person).
  6. Focus on facts, not feelings. A good example might be how Grandpa grew up in XYZ, so his childhood experiences framed his adult views about XYZ. Maybe he attended a segregated school. Maybe he had a personal experience with someone of another race that was unpleasant and it set the tone for his outlook on life. These aren’t excuses, they’re context. Maybe you could follow up with an experience from your life and how it’s been different. How you grew up with friends of many races. How you had this positive experience with someone of another race and how that’s shaped your view about XYZ.
  7. Ask questions and LISTEN. Like, genuinely ask questions to dig deeper and make space to listen to what the other person is saying.
  8. Pause before responding to anything; heck, if someone says something that you have a response to (but they’re still talking), write it down to circle back to when it’s your turn.
  9. Acknowledge what you’ve heard. Sometimes the easiest way to do this is to literally repeat back to them “so you’re saying because of this experience, you felt uncomfortable when I said this to you.”
  10. Wrap it up/make a game plan to move forward. Thank the person for taking time to talk with you, to engage in conversation with you, to explore different ideas with you. What do you want to do after this conversation? Do you want to continue the dialogue? Do you see things differently after this interaction?

Now, this isn’t a surefire way to guarantee you’ll change the world . . . but it is a roadmap that I’ve used to bridge gaps between parties that I work with on a daily basis. Honestly, I think a lot of people go about their every day lives and don’t actively look for opportunities where they could make it better.

Start with that friend who passively makes racist comments at a party; instead of uncomfortably laughing along or being silent, say something about how (and why) their comment makes you feel uncomfortable.

Start with volunteering at that organization that does outreach in your community. Donate to a cause that is already doing good. I saw a great one this morning about a Black hairdresser who works with transracial adopted children (e.g. a Black child and White parents) and she teaches them how to do braids and other hairstyles that compliment the child’s hair texture. Check out a link to a video here and her Instagram here.

Start with a conversation with your Grandpa, who might have grown up in a world with separate drinking fountains and only men on the Supreme Court.

Change takes time . . . so what are you waiting for?



Author: 2LWithIt

Spoonie Adventures in Books, Beauty, & Bullshit I'm a twenty-something year old recent law and business school grad living with a chronic health condition. Follow along on my shenanigans.

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