How to have the hardest conversation of your entire life, with Ramit Sethi & Sheila Heen

Conversation between Ramit Sethi and Sheila Heen (author and Harvard Negotiation Project faculty) about why people avoid difficult conversations and how to conduct them effectively. Covers both personal and professional contexts (marriage, friendships, roommates, workplaces), the role of feedback and identity, common unhelpful internal narratives (blame, attributions, squelching emotions), and practical framing for executing these conversations rather than just deciding to have them.
Chapters
Hey, it's Ramit Sethi here from I Will Teach youh to Be Rich and Brain Trust. I am absolutely thrilled today to talk to Sheila Heen. She's the author of two New York Times bestsellers. One is called D Difficult Conversations, one of my favorite books of all time. And her second book is On Receiving Feedback. Now we are about to talk about why we don't give feedback, why we let these things fester and we create all these stories in our head to avoid having those tough conversations. We're gonna dive into what to say, why we don't do it. Bad examples and tons of great examples. Stay tuned.
I'm Sheila Heen. I'm a faculty member at Harvard Law School and a member of the Harvard Negotiation Project. And. And I've written two books, Difficult Conversations. And thanks for the feedback. The Science and Art of Receiving Feedback. Well, even when it is off base, unfair, poorly delivered, and frankly, you are not in the mood.
Sheila, thanks for being here.
I'm so happy to be here.
I can't wait to talk about difficult Conversations because I think I ran across your book in early 2000s in a class on communication.
Yep.
And it blew my mind because I realized all the things you had written in your book were things that I had started to encounter. They were things like, well, number one, me wanting to avoid tough conversations.
Yeah.
When I had them, I would kind of go in guns blazing. You're wrong. Here's why I'm so logical.
Yes. Yes. I have my talking points.
Yes.
Yes. I laid awake last night thinking about them.
I strategized all the reasons you're bad and I'm good.
Yes.
And I read that book, and it's one of those books that you can read every year and you discover something new. So what I would love to do today is talk about difficult conversations. I'd love to talk about some examples that you've seen, maybe some that I've seen, and just reframe the way we have these conversations. Because most of the time the difficult conversations that I think a lot of us want to have are in our heads. We don't take the time to articulate them.
Yeah. You know, what you're describing has totally been my experience. And I think when I was in school, I thought, well, once I'm more experienced and more successful and more confident, the conversations won't be hard. Of course. And in fact, the opposite is true, which is that as you have more complex relationships and you become more senior in organizations or as an entrepreneur, you spend more and more of your time having difficult conversations. So you actually need more and more advanced skills.
Absolutely. And we're not just talking professionally. Right, we're talking personally.
Yes, personally, yeah. If you want to get married and stay married in particular, difficult conversations are at the heart of sort of what makes the relationship either start to deteriorate or to thrive and strengthen.
You know, I've noticed growing into my early 30s how friendships change as well. And one of the things that's been very striking to me is how when you're in college and you're seeing somebody all the time, there's a lot more opportunity to correct a wrong or, you know, you have that interaction. It's much more frequent when you're in your early 30s and you're seeing people less frequently. It's amazing how many relationships I've seen with where one errant comment will totally torpedo a 15 year relationship.
Yeah.
I wonder if you can talk a little bit about how personal relationships change over time, some of the observations you've made, and then we'll get into some examples too.
Well, so one of the things that has been interesting for me is the research that shows that there's like an optimal ratio between positive interactions and negative interactions. So if you look at marriage, for example, and there's a corollary, I think, with friendship, you know, like five positive interactions for one negative, five to one.
It's like Amazon reviews, you want to have a couple of negatives.
Yeah, yeah, exactly. So this is work by John Gottman up in Seattle. And you would think, well, wouldn't it be better if it was 10 to 1? Like we have 10 positive interactions for any one disagreement or raising an issue. And he says, but if that's your ratio, you're not bringing up things that you need to bring up. Wow. And so three and five years later, those marriages are the ones that are in trouble because people aren't having the conversations they need to have. And so when we work with people around improving their capacity to have these conversations, I say, here's what's gonna happen, ideally, which is you'll actually find yourself having more of them. But you'll, over time, what will happen is you're raising things earlier before they become a crisis or they've been festering forever. And I will also say that in addition to, over time, as we get older and have more long term friendships and relationships, I also think that, I don't know if it's social media, but email, texting, et cetera, has exacerbated the problem as well, because we're communicating with people less by phone and more by text or email or whatever. And email isn't dialogue. Email is serial monologue. Right. So I type out my perfect message to you about why that comment you made last year upset me, and that's why I haven't been returning your calls.
Right.
And you're triggered by the second paragraph, because no matter how carefully I word it, there's something I don't understand or I'm leaving out that leaves you feeling accused and defensive.
I was reading a Reddit thread. Reddit, for me, is one of the best places to learn about human behavior.
It's just utterly fascinating on full display.
Yeah. And one of them was, I live in a house as a young woman. She's like, I live in a house with three roommates. And we have this new roommate who just came in. She's a hoarder in terms of food. So, like, we can't even close our freezer because there's so much food and there's stuff in the pantry, et cetera. There's so much food now that there are roaches in our kitchen. Roaches. And she said, how do you. How do I talk to my roommate about this? Because I don't want to be rude. And that was so interesting. You have roaches living in your apartment and your concern is.
I'm more worried about being rude than about, like, getting ill.
Yes. And I think about that that really goes back to identity that's, like, so core that in this day and age, it's actually more important than health.
Yeah.
So what's going on there?
Well, so. So part of it is that she's not wrong that the way she's thinking about bringing up the conversation probably is not going to go well. So here's the problem. To understand difficult conversations, you have to look beyond what people are saying to what they're actually thinking and feeling. And the challenge is that in difficult conversations, what we're thinking and feeling is actually quite predictable. That's the good news, actually. There's an underlying structure to our internal voice, as we call it. But the problem is that the places our internal voice goes to are not helpful. Okay, so I'm focused on what I'm right about. Like, this is actually unhealthy and wrong, whose fault it is. Right. Blame is a big feature of our internal voice. Like, she's the problem and she needs to change. And also attributions about why the other person is acting the way they are. Like, she obviously doesn't care about us. Or she's probably mentally ill or something. And then I'm kind of squelching my emotional reaction because it feels like, well, I should. I don't want to open that can of worms. I got to keep that out. And then there's the identity stuff, sort of at the deepest level. So if she comes in guns blazing to explain why we're right about this, why this is your fault, you need to change, or else you don't care about us or something, it's not going to go well.
I want to unpack that. Because guns blazing is exactly the way that I think most of us imagine.
Feedback. Yeah.
So implicit in her question, how do I do this without being rude? Is that if I have this conversation, I'm gonna go in guns blazing. I'm gonna attack, she's gonna be attacked. It's gonna be a bad situation.
And you have lots of experiences that tell you, bingo, don't try that. It's not gonna go well. So then you're stuck.
You're stuck. You've painted yourself into a corner. But what I learned from your book and from your work is that it's one thing to make a decision that, yes, I want to have this difficult conversation. In concept, I want to have this difficult conversation. It's quite another to say, how am I going to execute that? First, let's agree that it's important to have the conversation. Then we can talk about how do we do it. And that's when I really started to learn the structure. Yeah.
One of the things we say in the book is there's no way to throw a hand grenade with tactics. And holding onto it once you pull the pin is no answer either. And so what it feels like is, I have this message about why I'm right and this is your fault. Or maybe this is my fault. Actually, sometimes we worry about conversations cause we feel so guilty. Like, I totally should have brought this up earlier. I screwed this up. So fault or blame is always a feature. It's not necessarily always pointed that way. Sometimes it's pointed this way.










