'Hard conversations don't fix hard things.'

5 questions for podcast host and author Anna Sale

If you haven’t heard super popular podcast Death, Sex, & Money, now is the time. It’s hard for me to even explain why you need to listen. Because you will hear a strip club patron talk about loyalty and transparency? Or because you will hear cross-racial friendships laid bare? Or because you will hear about near death experiences that led to much-needed divorce? I guess what I’m trying to say is that it’s a podcast about humanity—our deepest secrets, our biggest fears, our unspoken desires.

At the core of its success is Anna Sale, and the team she’s built, who do a magical job of creating a community out of a podcast and helping other people have the same kind of hard conversations they model on the pod. Now Anna Sale’s got a book out, called Let’s Talk About Hard Things. I knew my podcast co-host Nguhi was a big fan of Anna’s, so I invited her to do the interviewing this time around. Feast on this…

Nguhi Mwaura: You are one of my favourite interviewers because it always sounds to me as though its not just about the information, but a deep curiosity about why a person is the way they are. Do you still get those heart-pounding, dry-mouth moments when asking people about stuff they often don’t talk about?

Anna Sale: You know, I don’t. Because I think of it more as asking people about things that we aren’t comfortable talking about, or don’t have a lot of practice talking about openly, but that they actually want or need to talk about. I’ve found that a lot of the time, when you take care with how you ask about something and explain why you’re asking, even if it’s about something quite tender, people respond.

And I also like to tell people I’m interviewing that if I ask about something they don’t want to talk about publicly, they don’t have to answer and we can just move on to the next question. 

Tough conversations aren’t often a one-time thing. When these go wrong, or you mess them up, how do you think about moving through the icky place that says, maybe its not worth it vs. moving towards and building resilience around hard conversations?

When a tough conversation doesn’t go the way you want, I find it can be helpful to revisit it and begin with the observation that it went off the rails before. Starting by saying something like, "Now, I know the last time we talked about this it didn’t go well, but I'd like to talk about it again because..."

If you are still feeling that nagging pull to say something to someone in your life, it’s important to try again. It can also help to laugh about what went wrong the last time. Indicating a little self-awareness to your conversation partner can go a long way to invite them back in.  

You have little conversation sign posts that can help steer hard conversations, do you have any stand-out's or ones that that really resonate with you. For me: "what is the money for?" 

I also really liked: "What are you into?" as a guiding principle for sex converastions, because it's a really nice reminder that when we're talking about intimacy and romantic relationships, we’re comparing what we want and need to what our partner (or potential partner) wants and needs.

And in knotty family conversations, I do find, “Tell me that family story again,” to be a useful prompt. It reminds me that each member of my family has had their own distinct and individual experience, and it helps me understand them when I hear their memories of pivotal moments.  

Out of these hard uncomfortable topics, is there a particular one that you still find hard to talk about, even with all your practice?

They’re all still hard in different ways, but writing this book has made me realize what I can hope for from a hard conversation, and what I can’t. For example, when I want to comfort someone in grief, I still feel the urge and wish to be able to say something that would lift the pain of loss, but I am more clear that I can’t do that. Words can’t do that. But what I can do is express care, tell them I'm so sorry, offer what I remember about the person who’s gone. Hard conversations don’t fix hard things. But stepping towards them can make us feel less alone while we move through hard things.

Do you have a quote or words that you live by when it comes to the tough things and the conversations around them?

There are so many things people told me that I try to carry with me, but there are two that stand out. One is, “Do you want to be right or do you want to be together?”

That was something the comedian Hasan Minhaj told me his father told him to guide him in a conflict. Sometimes, it’s important you’re right and you stand up for yourself, and you take the consequences. Other times, it’s more important to be together, and you figure out which differences or conflicts you can let slide for the sake of a relationship. We have to do both at different times, sometimes in the same conversation!

The other line I love came from Karena Montag, a therapist who does anti-racism and restorative justice trainer. She told me she starts workshops with the guidance to “Expect and accept a lack of closure.” I find that to be a useful reminder for hard conversations, which can be thorny, evolving and ongoing, and also for life in general!

Anna wanted our donation to go to the Covenant House in her hometown of Charleston, West Virginia. (The Executive Director, Ellen Allen, is quoted in the sex chapter of Anna’s new book!)