How to Say the Hard Thing and Keep the Relationship | A Bit of Optimism: Feelings at Work | PART 5

Every lasting relationship has survived at least a few hard conversations. But most of us would still rather not have them... So we put them off and tell ourselves the tension will fade on its own. Instead it goes underground: into the stories we build about people, the resentments we quietly collect, and the side-texts we send about a colleague we won't talk to directly. But a hard conversation is a short burst of discomfort in exchange for something better on the other side: trust, collaboration, and a relationship strong enough to survive the next one. Feelings at Work is a special five-part series from A Bit of Optimism, where Simon Sinek and Alex Simon, founder of LifeShop, explore the human skills that shape how we work, lead, and build relationships. Together, they unpack the emotional challenges most of us face every day—from people pleasing and listening to giving feedback, taking accountability, and having difficult conversations. In this final episode, Simon and Alex take on hard conversations: why tension is telling us something useful, why the story we build about someone gets harder to undo the longer we wait, and what to actually say when it's time to have the hard conversation. Simon and Alex share tools like how to know when to bring something up so you don't show up hot, how to break the fourth wall and reset a conversation that's already going sideways, and the practice of “Watering Someone’s Flowers.” In this episode you'll learn: ➡️ Why tension is a smoke signal telling you to address something ➡️ How conflict is a team sport for mutual understanding ➡️ How to move from "you're the problem" to both of you facing it together ➡️ The "resentment gremlin" + why feeding it feels so satisfying ➡️ When to initiate a hard conversation ➡️ Why it’s important to start with a request for grace ➡️ “Watering someone's flowers”: the practice that softens any tension ➡️ What to do instead of “feedback sandwiches” ➡️ How to interrupt, reset, and take something back during a conversation Whether you're leading a team, dreading a review, or rehearsing the same speech in your car for the third week running, learning how to have hard conversations is an essential skill to build. And remember: a hard conversation isn't a sign that something has gone wrong. It's a sign that something matters enough to fix. This... is A Bit of Optimism. + + + CHAPTERS Chapters 00:00:00 When Conflict Turns People Into Monsters 00:02:16 Reframing Tension: It's a Sign, Not a Problem 00:02:43 The Resentment Gremlin: How Waiting Makes It Worse 00:03:50 Oh No, Let's Just Skip It: Why Hard Conversations Feel Impossible 00:08:01 The Passive Aggressive Company: When Tens of Thousands Avoid Feedback 00:10:02 When Passive Aggression Is The Solution to Conflict 00:11:15 What Actually Stops Us: Fear, Narrative Building, and Self-Righteousness 00:20:38 Conflict Is a Team Sport for Mutual Understanding 00:23:04 You're Not the Problem, I'm Not the Problem: The Problem Is the Problem 00:25:21 The Interruption Technique That Stops Character Assassination 00:26:27 Timing Matters: Not Too Hot, Not Too Cold 00:28:31 Setting a Goal: What Do You Actually Want From This? 00:29:44 Asking for Grace Grace: "I'm Going to Get This Wrong" 00:33:07 How to "Water Someone's Flowers" 00:38:02 Try This Instead of Feedback Sandwiches 00:40:25 Breaking the Fourth Wall: Pause, Reset, and Start Again 00:43:41 The Scaffolding Philosophy: Messy Humans Need Support Structures + + + Website: http://simonsinek.com/ Leaderful: https://simonsinek.com/leaderful Podcast: http://apple.co/simonsinek Instagram: https://instagram.com/simonsinek/ Linkedin: https://linkedin.com/in/simonsinek/ Twitter: https://twitter.com/simonsinek Facebook: https://www.facebook.com/simonsinek + + + About Alex Simon Alex Simon is the founder of Lifeshop, a school for adult emotional education and teaches emotional intelligence at Yale University. She teaches the emotional and communication skills we all should've learned in school—but didn't. She facilitates experiential workshops on how to have hard conversations, stop people pleasing, listen better, navigate major life transitions, and build healthier relationships. Her sessions are practical, deeply connective, and somehow shockingly fun. When she was 27, Alex created The Self & Other: In Theory and Practice, one of Yale's most sought-after courses. In 2025, she founded Lifeshop in New York to bring emotional education beyond the classroom and into everyday life. She also launched The School of Life in New York and leads workshops for organizations around the world. Before dedicating her career to emotional education, Alex worked as a management consultant at Bain and held strategy and operations roles across industries. She has also lived and trained at Plum Village and Esalen and completed dozens of programs in mindfulness, communication, and personal development.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  When I'm in a really intense conflict with someone, maybe I care about them, maybe I have loved working with them. I can't see any of that. Like, I see like a monster in front of me. When I'm able to relax that and be like, oh, you're not some evil being with bad intentions, but you're just a person who I seek to understand, who I want to help understand me, it changes everything. So now we can both win.

• 0:17Simon Sinek?

  That's so good, just to recognize that this person isn't a monster, it's just something that happened. Even that's a relief.

• 0:22Speaker 00

  For me, the most important thing, the thing that I always try to come back to is reminding myself of this one golden sentence. Conflict is a team sport for mutual understanding.

• 0:31Simon Sinek?

  You're in the car rehearsing exactly what you want to say about that thing that's been bothering you. The words are perfect, the tone is calm but firm, you're compassionate, you're clear, you're setting your boundaries, you're crushing it. Then you get to work, you see the person you need to talk to, and what comes out of your mouth is, hey, good weekend? We move on with our day, completely avoiding the hard conversation we needed to have. Or, we do say what we wanted to say, but it doesn't come out exactly like we rehearsed. We fumble our words, we say what we want to say in all the wrong ways, they get defensive and now it's even worse. Worse than if we had just said nothing. The reason this scenario is familiar is because most of us just plain suck at having difficult conversations.

• 1:15Simon Sinek?

  But here's the good news. Having uncomfortable conversations is a learnable, practicable skill. And with a few simple techniques, those conversations can go a lot smoother and actually bring people closer together. Instead of taking a summer hiatus, we are presenting a special five-episode series of A Bit of Optimism to go deep into some human skills, the things that help us connect, collaborate, and succeed in human relationships. That's why I invited Alex Simon, founder of Life Shop, where she teaches emotional intelligence, to join me. And over these five episodes, we will tackle some of the messier human interactions, like taking accountability, people-pleasing, listening, and giving feedback.

• 1:59Simon Sinek?

  And in this one, having hard conversations. Because in this age of AI, yes, you can get help drafting what to say, but the AI can't sit across from someone, look them in the eye, and actually say it. That part is still very human. There are a few major themes that we will cover in this episode. First, we reframe what's actually happening in conflict. Because most of us treat tension like something to avoid, when in reality, it's a sign. A sign that there's a misunderstanding or some sort of tension that needs to be addressed. And the minute we're able to reframe what tension means, the more open we become to actually leaning into that tension instead of avoiding it.

• 2:42Simon Sinek?

  Next, we'll break down why these conversations get harder the longer we wait. That's because tension doesn't just go away, and we're definitely not neutral in these scenarios. We tell ourselves stories about who's right and who's wrong, and we're usually right in our stories. And we start to become more and more sure of the other person's intentions. And before too long, we're making decisions and acting based on our stories, not what's actually the source of the tension. And finally, we'll give you a simple way to have that conversation that needs to be had. It's not about being more honest, or speaking up, or speaking your truth. It's about having a clear, repeatable approach to ensure that difficult conversations are more likely to go smoothly.

• 3:27Simon Sinek?

  So here's the hard truth about hard conversations. Few, if any, of us are real pros at this, and all of us could learn some techniques that make us better. If you enjoyed this episode, please remember to subscribe. This is A Bit of Optimism.

• 3:50Speaker 00

  Today, we are talking about hard conversations.

• 3:52Simon Sinek?

  No, no, I don't want to talk about a hard conversation.

• 3:54Speaker 00

  You're right, let's just skip it. It sounds hard.

• 3:57Simon Sinek?

  Sounds hard. No, it's too hard. Let's just, let's just suppress everything and be passive-aggressive. It's so much easier.

• 4:02Speaker 00

  Yeah, let's pretend like nothing bad is happening.

• 4:04Simon Sinek?

  I don't want to pretend there's nothing bad and there's no tension and everything's perfect. I don't want to have a hard conversation. I think that's most people at work.

• 4:10Speaker 00

  I think it's most people too. Well, I don't think we think of work as like the place where we have to learn how to have hard conversations. We are like, oh, marriage is hard, but we're not like, oh, my collaborative relationships with people will naturally have friction that will be really hard to navigate, and I'm gonna have to like muster emotional courage to do my job.

• 4:25Simon Sinek?

  You say this all the time, right? We understand that marriage is a relationship, or relationships are relationships, that we have to learn the emotional regulation and holding space for other people. Why? Because we want the romantic relationship to succeed, so we quote-unquote "do the work." We teach our kids how to manage their emotions and regulate their emotions so that they can have friends and be functional members of a society. But we don't talk about this stuff at work. And one of the big gaping holes at work is the ability to have a difficult conversation.

• 4:52Speaker 00

  Yeah.

• 4:52Simon Sinek?

  What are the circumstances? Why would we need to have a difficult conversation at work?

• 4:56Speaker 00

  To me, difficult conversations arise at work or in our relationships, something that needs to be addressed. So, for example, the way that I think about it is, if my arm was on fire, something would go off in my brain that would be like, ah, pain, pain, pain, and pain located in an arm, I would go to my arm, I would be able to put out the fire. Because the pain is like the smoke signal that's telling me, oh, there's a fire. To me, having hard conversations, having conflict in your dynamics with people at work, is the smoke signal that's telling me, hey, there's something off here. There's something about you that I don't get, there's something about me that you don't understand, there's something about our alignment that's off, like you think we're doing one thing, I think we're doing another, or I think we should go in this direction, you think we should go in that direction. And conflict is like the mechanism that brings it to our awareness.

• 5:40Speaker 00

  It's the thing that surfaces, oh, there's something that needs to be addressed.

• 5:42Simon Sinek?

  Tension.

• 5:43Speaker 00

  Yeah.

• 5:43Simon Sinek?

  And it's really funny. The funny thing about tension is, it's pretty much impossible for only one person to feel it.

• 5:47Speaker 00

  Yeah, sure.

• 5:49Simon Sinek?

  Like, if one person feels tension in a relationship, I can almost guarantee the other person at least can assess something's off.

• 5:55Speaker 00

  Something's off.

• 5:55Simon Sinek?

  Right?

• 5:56Speaker 00

  Yeah.

• 5:56Simon Sinek?

  Like, tension is not something that one person has.

• 5:58Speaker 00

  And I think when we experience tension, a lot of us have the instinct to avoid. Like, tension is bad, avoid, avoid, avoid. The logic there is, oh, if I pretend like it's not here, it's gonna go away on its own.

• 6:08Simon Sinek?

  Right.

• 6:08Speaker 00

  Right? Even though we have the lived experience over and over and over again of, oh, it doesn't go away on its own. And in fact, it gets exacerbated, it gets so much worse. Still, we, for some reason, believe if I don't address it, it won't be real and it'll kind of solve itself.

• 6:20Simon Sinek?

  Do you know when I came to realize the importance of learning to have the skill of having a difficult conversation at work? It was after the murder of George Floyd. And a lot of leaders, some of them like really good leaders, like people who, like, they know the skills, they do the work, said nothing. They didn't address it. And the reason was, they were so afraid of getting it wrong. They were so afraid of triggering somebody by accident. They were so afraid of not being perfect that they chose to say nothing. And that's when I realized, oh my goodness, these are good people who lack a skill and out of fear or concern chose probably the worst scenario,

• 7:00Simon Sinek?

  which is not lean into and talk about something that is difficult and is creating tension and is potentially emotionally flaring. And obviously, that's an extreme example. Most of the tensions we deal with at work are much smaller than racism. That's when I came to realize, we can teach people the skill and it makes work better.

• 7:15Speaker 00

  Yeah, I think hard conversations are so hard that they intimidate us into not having them.

• 7:20Simon Sinek?

  Yeah.

• 7:20Speaker 00

  And then what happens is that they kind of fester, and then by the time we have to bring them up, they've exploded. They're like way more intense than they needed to be. Whereas if we were able to have hard conversations sooner, to your point, if we had the skills to have the hard conversations. For me, it ends up being more like preventative care. Like, you have more smaller, hard conversations.

• 7:38Simon Sinek?

  Yeah.

• 7:38Speaker 00

  And then it feels more like communication, it feels more like you're like clearing the pathways.

• 7:42Simon Sinek?

  Communication is lubrication, right? And the inability to communicate creates, you know, grinding and tension and stress and strain. I firmly believe that in any organization, the better you are communicating, the more lubricated the machine. Let's just go through some of the circumstances under which the skill would be applicable. Obviously, there are personality challenges, you know, we don't get along with everybody all the time. Sometimes we just have different working styles, and we view the world through our own lenses. And sometimes, the way we like to work or the instructions we give, or the instructions we receive, don't land. Whether it's a performance issue or a behavioral issue. I knew a company, it's a huge company. There's an irony in this company because they thought that they taught these skills to other people. But they were so incapable of teaching these skills to their own employees

• 8:26Simon Sinek?

  that the whole corporate culture of tens of thousands of people was passive-aggressive.

• 8:30Speaker 00

  Yeah.

• 8:30Simon Sinek?

  Because nobody ever got hard feedback.

• 8:33Speaker 00

  I think passive aggression is such an interesting one. The way that I understand passive aggression is, it's the thing that you need to address is still coming out, it's just coming out sideways. And so instead of addressing it head-on in a way that can give someone the information that they need in order to make a change, it's like coming out in all these ways that are kind of hard to point to. For example, let's say you and I have a dynamic, and we both know that like if you said something in some way, I would react in a certain way. But I'm trying to be passive-aggressive because you've done something totally unrelated that's hurt my feelings or pissed me off. And so you say the thing, and we both know that I would react, and instead of reacting, I kind of don't do anything. I'm doing an invisible thing.

• 9:06Simon Sinek?

  Right.

• 9:07Speaker 00

  And then it would be crazy for you to be like, um, excuse me, Alex, normally you would have laughed at my joke. You can't do that.

• 9:13Simon Sinek?

  So I tiptoe around going, I know something's wrong.

• 9:16Speaker 00

  Yeah.

• 9:16Simon Sinek?

  I can't be like, what's wrong?

• 9:18Speaker 00

  Yeah.

• 9:19Simon Sinek?

  Because you're like, nothing's wrong.

• 9:20Speaker 00

  What are you talking about?

• 9:20Simon Sinek?

  What are you talking about?

• 9:21Speaker 00

  Yeah.

• 9:21Simon Sinek?

  Well, I made a joke, and you didn't laugh at it. Well, maybe your joke wasn't funny.

• 9:24Speaker 00

  Yeah.

• 9:25Simon Sinek?

  This may be a personality flaw, it may be an asset, I don't know, but I think, I think passive aggression is hilarious. And my very inappropriate and childish way of dealing with it is to deal with it literally, right? So, true story. I, early in my career, I had a little marketing company, and we rented space in somebody else's office. We did our thing, we were quiet in the back, and I put up a picture, just a small little picture to decorate my part of the office. Didn't hang it up high on the wall, I hung it really low, right next to my desk. The person whose other company this was, she's sitting like seven desks away from me, she's just over there, right? And she sends her assistant back to me. He comes over and says, um, Jane would like you to take your picture down? And I would say, um, tell Jane no.

• 10:11Simon Sinek?

  Go back and I'm giggling and like having a blast because just come up to me like, hey, Simon, we got an aesthetic here. You know, I know you want to make a little space for yourself. Let's compromise and come up with a way that you can do this. Maybe you can put a frame on your desk. I'm totally cool with that. Right. But it was so passive aggressive, you know, to send somebody else to like to do her bidding. I just thought it was hilarious. But now I'm fully aware that my childish way of dealing with passive aggression is only amplifying the tension and creating bad blood between us for my own comedy.

• 10:40Speaker 00

  For your sport.

• 10:41Simon Sinek?

  For my, for my sport. And I'm fully aware, not a good way to build a relationship when I'm renting space, when I'm renting space in somebody else's office. By the way, she clearly didn't have the skill to have it with me. If I had maturity and skills, I could have gone over to her and be like, hey, can we just talk about this? But I had neither of those things back then.

• 10:59Speaker 00

  Now look at you. Look what you are now.

• 11:00Simon Sinek?

  Well, I have more skills. I'm not sure I have the maturity. So I'll be like, I don't know, baby steps, baby steps. You know, it was 20 years ago.

• 11:07Speaker 00

  Okay. I'm curious, other than passive aggression, what are the things you notice for yourself? That get in the way of, of having hard conversations?

• 11:12Simon Sinek?

  There's a few things that get in the way of me having hard conversations. Obviously, you don't want to hurt somebody's feelings, especially if you know somebody's sensitive. You, you don't want to hurt somebody. You want to make them upset. So I think we avoid difficult conversations. Fear, as we talked about, like not wanting to trigger somebody.

• 11:26Speaker 00

  It's kind of like if I have food in my teeth, you know, it sucks to hear that I have food in my teeth, but I would much rather know.

• 11:31Simon Sinek?

  Yes, that's the person on the receiving end who'd be like, just tell me. But the person on the giving end doesn't know that. Once it eventually happens, hopefully, the person will be like, you, I want to know these things, but we don't know that.

• 11:43Speaker 00

  Yeah.

• 11:43Simon Sinek?

  So I think that's part of it. You know, we don't want to hurt somebody's feelings.

• 11:46Speaker 00

  Yeah. For me, one of the things that stops me from having hard conversations is believing my own story of them. Like, I think there's like a narrative building component that sometimes happens of like, oh, you're working with someone, they do something once and you're like, huh, weird, a little annoying. They do it a few more times and you're kind of thinking to yourself, okay, well, it's a little frustrating that they're doing this. And then they do it a little bit more. I kind of think that they are this way, like they are lazy or they are not that considerate, or they are not thinking about this.

• 12:13Simon Sinek?

  So the longer you wait, you, you build up a worse and worse narrative of the other person.

• 12:17Speaker 00

  Yeah. And you're like accumulating your own proof points, you know? And so then it goes from, oh, this thing happened once or a couple of times to this person is this way. I don't trust them. I don't want to work with them.

• 12:25Simon Sinek?

  Yeah.

• 12:26Speaker 00

  And so I think that like arc of narrative building also stops you from having hard conversations because the more you believe, oh, that this is something fundamentally wrong with that person, then the less faith you have in their capacity to change.

• 12:38Simon Sinek?

  Oh, that's an uncomfortable one because I think we've all done that professionally. We've all done it personally where a tension arises and reasonably quickly the snowball, you know, builds to the point where you have completely assessed and judged their character.

• 12:51Speaker 00

  Yeah.

• 12:51Simon Sinek?

  And find all the proof points to prove, to prove yourself right. That is so true. As we're talking about this, I thought of two other reasons why I have avoided uncomfortable or difficult conversations. One is when I'm afraid of ruining the relationship where if I address this difficult thing, I fear that they will react in a way by ending the relationship or ending the friendship. So I don't want to risk that.

• 13:10Speaker 00

  I feel like there's like a fear of the cat being out of the bag in that sense of like, sometimes I think that there's a truth of our relationship. And if we name that, then something about the relationship wouldn't be able to go on. And so I would rather, like you said, like, live in this weakened version of a relationship that doesn't actually feel like totally right. Because I'm worried, oh, if I name this thing, then the truth will be out and that'll be it.

• 13:30Simon Sinek?

  The other time I've avoided it is I think I've stopped caring. I'm thinking of a real life circumstance right now, actually, where I attempted it and it did not go well. The person couldn't hear me, didn't employ any listening skills. It was a very, it was a very hard conversation. In fact, they, they did everything that we recommend don't. They were hyper rational. They were very aggressive. They were right. I was wrong. We sort of muscled through it and came to some sort of like acceptable but imperfect conclusion. And then it happened again. And I'm at the point now where I could say something and I'm just like, you know what? Maybe it's not worth it. And I'm fully aware, and this is where I'm sitting in the stress right now, which is if I choose not to have the uncomfortable conversation, I'm basically

• 14:12Simon Sinek?

  accepting the loss of this relationship. And so do I start the mourning process and just end the relationship? Or do I try again? And so I'm going through it right now.

• 14:21Speaker 00

  So it sounds like you were trying to bring out something that was real for you and then you felt disappointed that they didn't like care enough to engage on a deep level. And so then you stopped caring.

• 14:29Simon Sinek?

  Well, it was worse than that. I was made to feel wrong.

• 14:33Simon Sinek?

  One of the things that makes me think, should I have this conversation or not with this person? Is I don't expect for it to resolve. I don't expect for them to suddenly have the skill of listening and making me feel heard. I don't expect to get the thing I need. But should I have the hard conversation just to have the relief? Because what's happening otherwise is I lie in bed every night and play over and over and over the thing I would like to say. And if I have that conversation, will that voice leave me at night? And with no expectation of resolution, I want to stop scheming what I would say and just say it. Or the other thing is just who cares? Just move on.

• 15:15Speaker 00

  Well, I think it depends on what kind of who cares.

• 15:16Simon Sinek?

  Depends, depends, depends on how much I value the relationship.

• 15:18Speaker 00

  Yeah. There's the like resignation, who cares? Let's move on. And then there's the, oh, sometimes I just need to accept, move on. And not everything's going to be exactly how I want it to be. And I think it really depends. I find it to be a really intense tragedy when I lower the ceiling of what I think a friendship or a relationship or a work collaboration is, is capable of. I want to go to some of the other things that I think stopped me from having hard conversations. One, I don't really know exactly what's going on here on a psychological level. I feel self righteous when I'm accumulating resentment about how someone else is doing something that's wrong.

• 15:51Simon Sinek?

  Oh, totally relate.

• 15:52Speaker 00

  I feel morally superior.

• 15:54Simon Sinek?

  Totally, totally relate.

• 15:55Speaker 00

  Yeah.

• 15:56Simon Sinek?

  And I know they feel the same way.

• 15:58Speaker 00

  Yeah. The way that I picture it is like, I have this gremlin version of me inside of me. She looks kind of like me, but she's like, and like every time I like collect something that someone else is doing wrong, I'm like feeding her. I'm like, here, take a cookie. You know, like I'm feeding my own little resentment gremlin. And somehow I feel that like I am superior and the other person is, is wrong for it. I think that that's one. And then I'm choosing not to bring it up. I'm choosing not to bring it up every single time. And like, that's how the resentment accumulates, like these like micro frictions that I would rather feel justified than be in open communication with someone. It's like so illogical. I still do it all the time, obviously, even though I know it's the same. Like there's, when I zoom

• 16:40Speaker 00

  out, I think what I'm doing in those situations is picking my like short term satisfaction over the relationship in the long term.

• 16:50Simon Sinek?

  But you said it right, which is that resentment gremlin is a self righteousness.

• 16:54Speaker 00

  Yeah.

• 16:54Simon Sinek?

  Which is if I can feed the resentment gremlin, then I can feel right.

• 17:00Speaker 00

  Yeah.

• 17:01Simon Sinek?

  And that helps me manage the tension, the discomfort, the anger and the frustration because at least I'm on the side of right.

• 17:07Speaker 00

  Totally.

• 17:08Simon Sinek?

  You know?

• 17:08Speaker 00

  Yeah.

• 17:09Simon Sinek?

  By the way, I'm sure the resentment gremlin feeds on that as well. Cause if you have no resentment, he loses a house and he has to go find another body to occupy.

• 17:16Speaker 00

  Yeah, which is way less fun.

• 17:17Simon Sinek?

  Which is way less fun for him.

• 17:19Speaker 00

  And I think it's also like built into our model of hard conversations. The water that we're swimming in of conflict is this adversarial model of like you versus me. I'm right, you're wrong. I want to prove to you why you're wrong and I want to prove to you why I'm right. I want to win the, the argument. Like, what does it even mean to win an argument? To be more right? Or to like be more hurt or more the victim party or something?

• 17:41Simon Sinek?

  I want to bring it back to work for just a moment, which is some difficult conversations are difficult because they're difficult in our minds, but they're also necessary. So for example, sometimes asking somebody for a raise can be excruciating and excessive planning and stress causing. But sometimes you have to have that conversation.

• 17:59Speaker 00

  Yeah.

• 17:59Simon Sinek?

  And it doesn't mean I think bad has happened or, you know, your boss is a bad person or anything like that. It just means the conversation needs to happen.

• 18:05Speaker 00

  Yeah.

• 18:05Simon Sinek?

  Or you feel like you're capable of more, or you want to redirect your career, or you're not enjoying this part of the job and you want to try some other part of the job. And I think these are difficult conversations because we create stress around them because we don't know what the outcome is going to be. We don't want to piss somebody off. We don't want to get it wrong. We create stakes that there may or may not be there. And I just want to point to the fact that not all difficult conversations are personality conflicts or disagreements. Some of it is, quite frankly, the normal course of a career.

• 18:31Speaker 00

  Yeah. And I think that's the most important point is like, it's normal. It's going to happen.

• 18:36Simon Sinek?

  They have to happen.

• 18:37Speaker 00

  They have to happen.

• 18:38Simon Sinek?

  If you feel like you need a raise, or you want to try a different job and you never self advocate, then you're going to sit there resentful that the company doesn't appreciate you, your boss doesn't appreciate you. And then you feed the resentment gremlin and you start resenting the person or the company.

• 18:50Speaker 00

  When you haven't done anything to even make a change.

• 18:52Simon Sinek?

  When, when you haven't leaned into your ability to have that difficult conversation.

• 18:56Speaker 00

  Yeah. I think when we realize that hard conversations are inevitable and they're normal and they're just like part of the experience, it changes where we're putting our energy. Because instead of laying there at night lamenting the fact that the problem is ongoing, while we're simultaneously not doing anything different to try to change it, when we realize, oh, this is just part of the process. It's like a normal thing that's going to have to happen. Then we redirect our energy from trying to avoid, avoid, avoid hard conversations to like, how do I do it?

• 19:21Simon Sinek?

  Yeah.

• 19:22Speaker 00

  And then we can actually engage with, okay, there are things that I can do to make this easier.

• 19:25Simon Sinek?

  So this is a good segue.

• 19:26Speaker 00

  Yeah.

• 19:27Simon Sinek?

  Now let's talk about.

• 19:27Speaker 00

  How do we do it?

• 19:28Simon Sinek?

  Let's talk about how to have a hard conversation. The stuff that we're talking about here, look, it's valuable at every level, but I think the skill becomes very pronounced that you realize you don't have it when you're in middle management, or when you were newly promoted to a position of leadership, or you have to do, you know, your first review of somebody who reports to you. And the review isn't stellar. Very often, I think people, well intentioned, bungle it. And they either really do hurt someone's feelings, or it doesn't get heard. The information that you're trying to communicate doesn't, doesn't land.

• 20:01Speaker 00

  Yeah.

• 20:02Simon Sinek?

  Even though you know you have to communicate it. So you have to have the, the difficult conversation because it's my annual review and you got to give me the, News, but because we don't have the skills on how to have a difficult conversation, it becomes self fulfilling. It actually does become a mess because we don't know how to deliver the news. So I think the skill is, just as we said, it's a regular occurrence to advocate for yourself up in the hierarchy. It also is a regular occurrence in performing your job when you're in middle management or a new leader. So it's just part of the job and our companies don't teach us.

• 20:30Speaker 00

  No one teaches us.

• 20:30Simon Sinek?

  No one teaches us, except for now. Okay, Alex, you have been teaching this stuff for years. What is the first step that people can learn on how to have a difficult conversation?

• 20:38Speaker 00

  For me, the most important thing, the thing that I always try to come back to when I'm having a hard conversation is reminding myself of this one golden sentence, conflict is a team sport for mutual understanding.

• 20:48Simon Sinek?

  Let's say that again, conflict is a team sport for mutual understanding. Break that down.

• 20:53Speaker 00

  What I was saying earlier about conflict being something that's inherently adversarial is the you versus me, right? Wrong, winner, loser. That crowds out the ability to actually understand each other. And so if conflict is the mechanism through which the important information that we both need to know to do our jobs, to be in our relationships, to understand each other, that's how this thing is getting surfaced. Okay, well, how do we actually understand this thing? And so to me, conflict is not something that I want to win or lose. I think we can all win if we both leave and you understand me and I understand you. I understand your context. I understand what's going on for you. I understand what needs to happen now.

• 21:31Simon Sinek?

  Inherent in the concept of conflict is that there's not a person.

• 21:34Speaker 00

  Yeah.

• 21:34Simon Sinek?

  So it recognizes that it's me and.

• 21:36Speaker 00

  Yeah.

• 21:37Simon Sinek?

  Which I think is interesting.

• 21:38Speaker 00

  And it takes us out of what we're normally like, for me, when I'm in a really intense conflict with someone, it's tunnel vision.

• 21:43Simon Sinek?

  Right.

• 21:44Speaker 00

  You know, like I look at this person, maybe I love them. If it's a personal relationship, maybe I care about them. Maybe I have loved working with them, whatever it is, and I can't see any of that. Like I see like a monster in front of me almost. And so when I'm able to relax that and be like, oh, you're not some evil being with bad intentions who's out to get me, but you're just a person who I seek to understand, who I want to help you understand me. It changes everything. So we can both win.

• 22:06Simon Sinek?

  So good. That is such a great framework to just admit to ourselves that this one instance, this one tension, all I see is a monster and I forget everything else that preceded it. And just to recognize that this person isn't a monster, it's just something that happened. They're advocating for themselves. They're doing something in their self-interest, which is fine. Whether they did it right or wrong is irrelevant. And just recognizing that, even that's a relief.

• 22:32Speaker 00

  Yeah.

• 22:33Simon Sinek?

  That's good. Keep going.

• 22:34Speaker 00

  Normally, when we're in a conflict situation, we look at the person who's like doing something wrong and we locate the problem in them. Like you are the problem this way that you are.

• 22:42Simon Sinek?

  No, we find a character flaw. They clearly don't have a capacity for dot, dot, dot.

• 22:46Speaker 00

  Mm hmm. Yeah. And we really believe that.

• 22:47Simon Sinek?

  I even just said it to you in recounting my experience, like they have no capacity for listening.

• 22:53Speaker 00

  Yeah.

• 22:53Simon Sinek?

  They don't know how to hold space. They're always rational. I literally just did it.

• 22:57Speaker 00

  And we believe it because we've been accumulating the proof.

• 22:59Simon Sinek?

  And I've completely assessed their entire character based on one tension I'm sitting in.

• 23:03Speaker 00

  Yeah. And so the core perspective is like, you are the problem and I am not the problem. And so what happens is it's you versus me. You're the problem. I'm not. So when we think about conflict as a team sport, what I try to remind myself of is instead of having the problem be in you, it's like, okay, how about you shift to the side of the table that I'm on and we're both facing the problem together of like, what is the situation that we're?

• 23:24Simon Sinek?

  Like we are in tension. That is the problem.

• 23:26Speaker 00

  Yeah, there's something that's going on between us that we both don't fully understand, that we can try to understand together.

• 23:31Simon Sinek?

  Yeah.

• 23:32Speaker 00

  And it's, it's so beautiful. The image that always comes to me is like a river and there's this kind of flow through the river. And when we don't bring things up, it's like, oh, we're putting all these rocks in the water can flow. And we're just like sitting in that every single day. And so when we can understand each other and we can remove some of the blocks, things can naturally flow and we're doing that at work all the time.

• 23:52Simon Sinek?

  And we build narratives about each other, you know, teams build narratives about their colleagues. We build narratives about our bosses. We build narratives about our employees. Like we're constantly building narratives and labeling people based on one or two experiences, finding information. And then the problem is, is we perpetuate those narratives. Oh, the lazy one.

• 24:08Speaker 00

  Yeah.

• 24:08Simon Sinek?

  Oh, the stupid one.

• 24:09Speaker 00

  Yeah.

• 24:09Simon Sinek?

  Oh, the angry one.

• 24:10Speaker 00

  And we triangulate with other people. I think this is another thing that happens a lot. It's like triangulating is like, oh, there's something that's going on between you and me. But when we're in a meeting, you, me and our other coworker, I'm side texting our other coworker like, oh, can you believe Simon's doing this? Oh, classic again. And so then we're building narratives. So we're not just accumulating these resentments and building these stories in ourselves, but we're looking to other people to confirm them because the more other people I can get on my side, oh yeah, he's the problem.

• 24:35Simon Sinek?

  And now what that is, is gossip and gossip is one of the most destructive things inside a company. I know a company, they considered gossip a fireable offense. And they said, if you have a tension, you have to learn to lean into it with somebody. And don't say anything behind somebody's back that you wouldn't say to their face. And this is different from venting about work and venting be like, oh, you know, blah, blah, blah was an idiot today. Like, that's fine because it's, it's labeling a behavior that was today. It's not assessing their character.

• 24:58Speaker 00

  Yeah.

• 24:58Simon Sinek?

  You know, venting about work is healthy, but gossiping about people, we did a thing at work where I recognized that we were building narratives about each other. And I, I realized it had to stop. What I implemented was I said, okay, here's the rule. I've noticed we've done it at the leadership level. I'm sure it's happening at every other level. It stops today. Which is if somebody says something that assesses somebody's character, they're lazy, they're stupid, they're an asshole, whatever it is, right? I need anybody who's in that conversation to interrupt and say, that may be true. They may be lazy or they're tired, they're overworked, they're overwhelmed. And simply acknowledging that there are other possibilities that are creating that behavior makes everybody go, oh yeah.

• 25:37Simon Sinek?

  And that technique not only has dramatically improved our culture, um, but I just think it's, it's just a healthier way of being that we're all taking responsibility for our colleagues and each other and a healthy place to come to work.

• 25:48Speaker 00

  Yeah.

• 25:48Simon Sinek?

  So that's been very, very helpful.

• 25:49Speaker 00

  Mm hmm. Cause like, once one of those narratives gets planted and mutually agreed upon by everyone, it's so hard to unself that.

• 25:56Simon Sinek?

  And that person is now playing defense for the rest of their job until they get forced out or quit.

• 26:02Speaker 00

  Yeah. And everyone loses. Like it sucks for everyone.

• 26:05Simon Sinek?

  So it's a lose, lose. Yeah. Okay. So the first element of the difficult conversation is the mindset, which is it's me and you versus the problem. And I recognize that you're not a monster. This is one thing that has happened, maybe more to, but the point is this is not everything about who you are. There's a conflict that exists with us, not necessarily between us, but it's on the table. Okay. So one is mindset. What happens next?

• 26:27Speaker 00

  Okay. The next thing is figuring out when is the right time to bring something up. And I think that there are kind of two extremes here. There are people who bring something up while the iron is hot. And then they're not able to actually like listen and engage. Like you're really inflamed, you're angry, you're dysregulated. That is not going to be the situation in which you're going to be able to have the most productive conflict. You're not going to be able to be like, huh, conflict is a team sport for mutual understanding. What an excellent opportunity for me to understand this person who is also a monster, you know? So I think you don't want it to be while like in the heat of the moment necessarily. And then on the other end of the spectrum, there are people who wait way too long. And so they like wait till the heat of the moment passes, but then they're like, well, it's not that important to bring up right now. Okay. Well, now it's been too long. And so they wait too long and they sweep it under the rug.

• 27:08Simon Sinek?

  Or they bring it up and create a tension that actually, because it's still festering in their mind.

• 27:12Speaker 00

  Exactly.

• 27:13Simon Sinek?

  But in reality, it's actually dissipated to some degree. So now you're actually taking the spark and actually pouring gasoline on it and making a fire.

• 27:19Speaker 00

  So I think it depends on where you naturally are. Like some people don't wait enough time and some people wait.

• 27:24Simon Sinek?

  So the point is middle.

• 27:26Speaker 00

  In the middle. Yeah.

• 27:27Simon Sinek?

  But just don't do it in the heat of the moment. Don't wait too long. Do it somewhere in between.

• 27:31Speaker 00

  So for me, I try to wait until it's no longer dysregulating my system.

• 27:35Simon Sinek?

  So you're no longer angry or rather you won't show up hot.

• 27:38Speaker 00

  Yeah, I won't show up hot and it's still alive. It's still relevant. I've had a little bit of distance from it. I think the key is in that period of pause is to express that I'm taking a period of pause because I care for maintaining something.

• 27:52Simon Sinek?

  You, you need to get yourself to the right place so that you can have this difficult conversation constructively. Cause you can have it destructively too.

• 27:58Speaker 00

  Totally. It's not just taking the time that you need, but it's also communicating that you're doing it because you want to set everyone up for the conditions for it to go as well as possible. So it's like, okay, in this moment, I don't feel like I can listen to you and I really want to be able to do that. Like sometimes, let's say someone's like, hey, can you talk? And you're doing your thing where you're waiting to calm down, but you don't respond. I don't think that's that cool.

• 28:18Simon Sinek?

  That's the passive aggressive.

• 28:19Speaker 00

  Yeah. And so I would say, yes, I want to talk. Right now I feel like I'm too activated to be able to have this conversation in a way that I would want to.

• 28:26Simon Sinek?

  Can we do another couple days?

• 28:27Speaker 00

  Yeah.

• 28:28Simon Sinek?

  So mindset, timing.

• 28:30Speaker 00

  Mindset, timing. Another thing that I like to do is come back to my intention for the conflict.

• 28:34Simon Sinek?

  Like I'm looking to feel heard. I'm looking for resolution. I'm looking for action. I'm looking.

• 28:38Speaker 00

  Yeah. It's like, hey, I know that we both care about this thing. I want to figure out a way to communicate about it so that we can get to this place that we want to both be in. So it's both coming back to my intention and maybe to our shared intention.

• 28:47Simon Sinek?

  And setting a goal, right? So knowing the reason you're going in, otherwise you're just coming in with the emotion.

• 28:52Speaker 00

  Yeah.

• 28:52Simon Sinek?

  And there's no destination set for the path you're about to journey on.

• 28:54Speaker 00

  Exactly. And the thing that I think works really brilliantly about this is that it actually does two things. First of all, it knocks me out of the normal culture of like, I want to win. I want to show why I'm right. Cause that's like, not actually our highest intention a lot of the time. It's more like our knee jerk reaction. And so I like to first remind myself of what my actual goal is for this thing. And that changes the frame. So that's the first thing that it does. And then the second thing is that I not only align with myself, but also start the conversation by naming it out loud, which creates an accountability of like, hey, let's do this thing that's bigger than either one of us is. It like reminds us that we have a shared mission. And then also if I can feel myself slipping into like, well, you're wrong for this reason and I'm justifying myself and this and that. Then I can remind myself that I'm, I want to.

• 29:39Simon Sinek?

  I want to get to the goal. Mindset, timing, setting a goal. Can I? Here's something I do.

• 29:45Speaker 00

  Yeah, tell me.

• 29:45Simon Sinek?

  I make a request for grace. And I've done this before professionally, personally. I need to have a difficult conversation. So I alert somebody about what's about to happen. Because what I've learned is otherwise you come in hot. And even if you you aren't, that's how it's received. And you get very defensive responses. And so by preparing somebody that this is not going to be fun, there's a beat that they can take a breath. And I ask permission because because you know, we talk about timing.

• 30:07Speaker 00

  Yeah.

• 30:07Simon Sinek?

  Like, the timing might be great for me.

• 30:09Speaker 00

  But it might not be.

• 30:09Simon Sinek?

  But not be great for them. So I need to have a difficult conversation. Can we have it now?

• 30:14Speaker 00

  Yeah.

• 30:14Simon Sinek?

  And they might go, yeah. Or they go, can we do it in an hour? I'd be like, yeah, we can do it in an hour. I regulate the timing. So I ask permission. I I alert what is about to happen. And so in other words, I'm setting their mindset. And I'm making sure the timing works for them too. Because I also want them to show their best self. Maybe they're tired. Maybe they're dysregulated. Maybe they're pissed off. You know, maybe they're still angry at me.

• 30:35Speaker 00

  Yeah.

• 30:36Simon Sinek?

  Simon, I'm still angry at you. I can't do this right now. Okay. You know, so I need to have a difficult conversation with you. Is now a good time? Yes, it is. And this is why I ask for grace. I say, listen, I I know I have to have this conversation with you. I also would rather not. Like, it's so much easier for me not to do this right now. For the good of the relationship, I want to see you thrive here. I want to see you do well, and I want to be supportive of you. I have to have this conversation with you. I'm gonna get some things wrong. I'm gonna say some things badly. And just work with me. I'm I'm trying. And by asking for grace upfront, what I've learned is the times that I haven't asked for grace, if I do accidentally misframe something, say something unclearly, say something wrong, they will latch on to it.

• 31:20Simon Sinek?

  And now I'm playing defense. I'm like, well, that's not what I meant. They're like, well, then why are you telling me this? And so it it actually goes sideways. And by asking for grace upfront, when I get something wrong and it and they hone in on it or it triggers them, I can back off. I can be like, that I got wrong. I'm sorry, that was the wrong thing to say. I take that back.

• 31:38Speaker 00

  Yeah.

• 31:39Simon Sinek?

  And they go, okay. Because they gave me permission at the beginning. And if they forget, I'd be like, you you remember, I said, I'm gonna get something wrong, please. You know? And so I help them get on the right mindset with me. I check in on their timing. I ask for grace because it is complicated and difficult. And I'm not an expert. But I need to do this. And I found that that framing has been immensely helpful.

• 32:01Speaker 00

  I really love that. I mean, for me, it sounds like you're creating a sense of togetherness of like, we have to have this hard conversation. And I'm a human being and I'm gonna try my best.

• 32:10Simon Sinek?

  By the way, I'd rather not have this.

• 32:12Speaker 00

  Yeah.

• 32:12Simon Sinek?

  Like, it is so much easier for me not to do this. I can just ignore it. That would be the better option for me.

• 32:17Speaker 00

  Yeah.

• 32:17Simon Sinek?

  But I'm doing this because I actually really care.

• 32:20Speaker 00

  And I'm willing to take the short term discomfort.

• 32:22Simon Sinek?

  Over the long term discomfort. I'd rather have a lot of discomfort now rather than the slow drip of discomfort for a long period of time.

• 32:28Speaker 00

  Which is the opposite of what we normally do.

• 32:30Simon Sinek?

  Which is because that's actually more cancerous.

• 32:31Speaker 00

  Yeah.

• 32:32Simon Sinek?

  Than than what we're gonna deal with now.

• 32:33Speaker 00

  Okay, can I share kind of a crazy one?

• 32:35Simon Sinek?

  Yeah.

• 32:35Speaker 00

  But it's my favorite one. I think I've told you, but I spent a few months in a Buddhist monastery in France. They have a lot around.

• 32:40Simon Sinek?

  Do you speak French?

• 32:41Speaker 00

  No, it was no, it's mostly in English and in Vietnamese.

• 32:45Simon Sinek?

  Okay.

• 32:45Speaker 00

  Which I also don't speak.

• 32:46Simon Sinek?

  Was there wine? That's all that matters.

• 32:48Speaker 00

  Absolutely not.

• 32:49Simon Sinek?

  What?

• 32:49Speaker 00

  And it's in Bordeaux.

• 32:50Simon Sinek?

  Come on.

• 32:51Speaker 00

  No wine.

• 32:51Simon Sinek?

  What a waste.

• 32:53Speaker 00

  It's a monastery.

• 32:53Simon Sinek?

  I mean, they're French monks, though. French monks.

• 32:55Speaker 00

  No, they're Vietnamese. And monks don't drink.

• 32:58Simon Sinek?

  I mean, what a tease to do it in Bordeaux.

• 33:00Speaker 00

  I know. Anyway, they have so much that they talk about about conflicts and having hard conversations. It's amazing. My favorite trick of all, it has a kind of insane name, but I'm gonna tell it to you because I think it's more likely to stick in your head. But it sounds fluffy. But basically, one of their most magic tricks is called watering someone's flowers, which is a very simple but powerful act of telling someone nice things about them. Sounds so simple. But again, when I'm in the the tunnel vision of conflict, it's often impossible for me to think of a good thing about someone.

• 33:32Simon Sinek?

  Because there's nothing good.

• 33:33Speaker 00

  There's nothing good about them.

• 33:33Simon Sinek?

  Clearly.

• 33:34Speaker 00

  Yeah.

• 33:34Simon Sinek?

  I like your hair.

• 33:35Speaker 00

  That, okay, that's actually a great example. So for example, when I, right after I got back, I was in a conflict with my best friend. I have a best friend. She is my soulmate. I think she is the greatest person on the planet. I love truly everything about her. And at the time, this was our biggest fight that we've ever gotten in. And we were in the thick of it. And she was like, Alex, surely you have some tools that we could try to use in this moment. Like, don't you teach this stuff? I said, okay, let's water each other's flowers. And explained what it was, the very simple act of saying nice things back and forth to each other. And she said, okay, let's try it. You start. And I was like, Jesus.

• 34:07Simon Sinek?

  I like your hair.

• 34:10Speaker 00

  And I looked at her, truly my favorite person on the planet. And I could not think of a single nice thing to say.

• 34:16Simon Sinek?

  Oh, my goodness.

• 34:17Speaker 00

  And I was looking at her for an embarrassing long amount of time. And she knew that I couldn't think of anything. And I was looking at her, looking at her, until I like eked one out. But it was like such a small, nice thing. And it was like more fact based than anything.

• 34:30Simon Sinek?

  Nice pants.

• 34:31Speaker 00

  Yeah, that that kind of thing. Like, I like this, whatever.

• 34:34Simon Sinek?

  Those are great shoes.

• 34:36Speaker 00

  Totally. But I said it. And then it was her turn. And she also kind of struggled. And she said one that was like also a little too small. But it was also a little bit nice. And it softened me a little bit. And then it was a little bit easier.

• 34:48Simon Sinek?

  And you're like, they are good shoes.

• 34:50Speaker 00

  You're right, I do have good hair. And then I said another one back to her. And it was a little bit bigger, a little bit more meaningful. And I could feel that she was softening a little bit. And then she said one back to me. We went back and forth. And then it became more substantive. And maybe it took like six minutes. And our whole conversation was different. And where we were once kind of like steeled up against each other, like you versus me, you're evil and wrong, and I'm right and morally justified. All of a sudden, the armor could soften.

• 35:22Simon Sinek?

  So here's what I'm hearing, right? And this is really important. So we've talked about mindset, timing. We've talked about having a goal, stating that goal, or not, but having a goal, asking for grace.

• 35:32Speaker 00

  Yeah.

• 35:33Simon Sinek?

  And what I like here is about affirming the other person.

• 35:35Speaker 00

  Yeah.

• 35:35Simon Sinek?

  Because conflict is hard. And for some, having leaning into a conversation may be simply fact based. Like, here's your performance, here are the numbers. And for some, it might be laced with shame and childhood. You know, an aggressive parent who cared only about grades and how people receive information and how people intend the information are not the same thing. I actually do like the phrase, and I don't like fluffy stuff. But I do like watering someone's flowers. I think that is actually a beautiful metaphor.

• 36:01Speaker 00

  Yeah.

• 36:02Simon Sinek?

  To lean over someone's windowsill, you know? Just giving them some affirmation that I think affirms not only that you recognize their value. I've made this mistake without doing that. Because I'm like, let's deal with the issue without doing that. It does make them feel undervalued, especially if there has been tension. Now, this difficult conversation is affirming that I don't value them. And so giving them some affirmation about their talents, their gifts, their contributions to the team, and people love working with them, is a good level set.

• 36:31Speaker 00

  Yeah. And then it allows people to hear the things that are harder.

• 36:34Simon Sinek?

  Because they recognize that you don't think I'm a dumbass.

• 36:36Speaker 00

  Yeah. And I think you're thinking about it in terms of one of the impacts of it, which is how does the other person feel when you water their flowers? And for me, what I've also found, maybe even more shocking, is how it changes my perspective. All of a sudden, instead of only seeing this one piece of the puzzle, I'm able to see the whole tapestry of like all the other things that are actually going right. And often, when we're having a hard conversation, we're only fixated on the ways in which things are going wrong. I want to say one more thing about watering flowers is because there's so many different ways to do it. I really love to start my hard conversations with it because I think it just starts us off in a different place. What do I appreciate? What's working well? What do I want to see more of? And just like, like you said, validating the person as a whole human being, which creates the ability to be listening and to be engaging and to be collaborative and to be creative throughout the rest of the hard conversation. I find that it works really well. So sometimes I'll start it off.

• 37:20Speaker 00

  And then sometimes I'll also keep it in my back pocket. If there are these moments where we feel like things are becoming adversarial, I'll either say, hey, can we pause and and try something else right now? Or I'll even just spontaneously say a nice thing about someone. Like, you don't need two to tango. So I think oftentimes with with hard conversations, people are like, well, what if the person I'm having a hard conversation with isn't like this? And the way that I think about it is like, you can lead the conversation in the way that you want it to be led. And so if you want it to be led in a way that validates the other person's humanity and creates a possibility for something other than just the things that are going wrong in the dynamic, then you can say that. Like, you can kind of spontaneously be like, okay, well, I also just want to honor that these are the other things that I appreciate about you.

• 37:59Simon Sinek?

  Let me throw a wrench in the works here.

• 38:01Speaker 00

  Throw a wrench.

• 38:02Simon Sinek?

  I hate feedback sandwiches.

• 38:03Speaker 00

  Yeah.

• 38:04Simon Sinek?

  I I despise them. Tell me something generic and bullshitty positive, something really specific and hurtful and negative, and then something generic and bullshitty and positive again, because that's what somebody taught you to give a feedback sandwich. And I find it pandering when in in a difficult conversation, somebody starts watering my flowers. And I can sense it's some technique they've learned or some bullshit they're trying to say to me to make me feel good in this moment. I actually find it very distracting.

• 38:32Speaker 00

  Yeah.

• 38:33Simon Sinek?

  And I think it has to be genuine.

• 38:35Speaker 00

  Yeah.

• 38:36Simon Sinek?

  Because if they say, well, Simon, you know, you're a good listener. I'm like, signifying nothing.

• 38:41Speaker 00

  Yeah.

• 38:41Simon Sinek?

  In this moment, we're talking about this. So thanks for the compliment, not interested. Like, that would probably be my response.

• 38:48Speaker 00

  Yeah.

• 38:49Simon Sinek?

  You know? I find it pandering. And so if you're gonna pay me a compliment, it has to be relevant to the conflict. It has to be relevant to the difficult conversation.

• 39:00Speaker 00

  It has to also be real.

• 39:01Simon Sinek?

  It has to be real.

• 39:02Speaker 00

  It's not a tactical thing. It's not a box that you have to check.

• 39:04Simon Sinek?

  Not a tactical thing.

• 39:05Speaker 00

  That's also what I feel about the feedback sandwich. It's like, normally, it's just a box you have to check to get to the actual thing that you want to say. Whereas this is like, you're saying something real that wouldn't normally fit into your perspective in this moment.

• 39:15Simon Sinek?

  I'll give you an example how it could work with me, right? Simon, one of the things I admire about you is that you talk about grace. I think you're good at grace. And so because you are good at grace, my ask is, will you make sure to give me grace in this? Because I know you're good at it. So I'm like, I am. Thank you very much. That would be a relevant and good use of watering my flowers because it's relevant to what we're engaged in.

• 39:41Speaker 00

  And it's authentic.

• 39:42Simon Sinek?

  And it's authentic.

• 39:43Speaker 00

  And people can feel your truth. Like, we think that we're, we think that we can kind of do the theatrics of things and that it'll work. It'll work if you're doing it authentically. And then that's, that's how it will work. If you're like, performing it, it won't do anything.

• 39:55Simon Sinek?

  And I have one more thing to add to our checklist.

• 39:57Speaker 00

  Yeah.

• 39:58Simon Sinek?

  Which is at any point in a difficult conversation, and you've talked about this a few times, you're allowed to interrupt and reset and say,

• 40:04Speaker 00

  Yeah.

• 40:05Simon Sinek?

  this is not going well. This is not going as I planned or as I intended. Can we interrupt and just take a step back? And then you can refer to some of your other techniques, which is, is now the wrong time? Or can I just tell you what I'm intending to get out of this? Or like, let me just tell you something that I think is wonderful about you before we go too off the rails here, right? Because it's getting heated and I just want you to know. And so you can interrupt and reset at any point.

• 40:28Speaker 00

  Yeah.

• 40:29Simon Sinek?

  And go back to any of the other things and sometimes even start again. Like, that works too.

• 40:34Speaker 00

  Yeah, I love that. I call it breaking the fourth wall of like, when sometimes you're in the theatrics of it and you just need to pause the scene. And so I will often ask to pause and be like, wait, can we stop for one second? I feel like we're, we're going in this direction that doesn't feel like it's going to be productive for either one of us. I'll also personally ask for like a take back. Like, I just said this, but actually, I don't mean it. Can I please take it back?

• 40:51Simon Sinek?

  And because you asked for grace upfront, you're good to go.

• 40:53Speaker 00

  Or I just said this, but it's actually not totally accurate. I misspoke. And that's the opposite of what we normally do. Normally, when we say something we don't mean, for some reason, we dig our heels in.

• 41:03Simon Sinek?

  We double down.

• 41:04Speaker 00

  We double down.

• 41:04Simon Sinek?

  Because we'd rather, we'd rather not be wrong.

• 41:06Speaker 00

  Then, then.

• 41:07Simon Sinek?

  Then take it back.

• 41:08Speaker 00

  Yeah. I try my best to drop the like ego part of me that wants to like fight and win. And also, this also works in reverse, right? Like, sometimes, I don't know if you have ever experienced this, but you're in a hard conversation with someone and someone says something and you know they didn't mean that thing.

• 41:21Simon Sinek?

  Yeah.

• 41:21Speaker 00

  But it kind of proves your point.

• 41:22Simon Sinek?

  Yeah.

• 41:23Speaker 00

  So you double down on it, but you both know that that's not what they meant. But that's also about winning and like you versus me and not, hey, I want to understand you and like, let's face the problem together. And so, breaking the fourth wall is something that I try to do anytime, even if I notice something that will block me. Like, for example, for me, something that often comes up is, I have the desire for my pain to be recognized first. I want them to tell me that they messed something up.

• 41:46Simon Sinek?

  Yeah.

• 41:47Speaker 00

  Before I'm willing to also admit that I messed something up.

• 41:49Simon Sinek?

  I'm like that.

• 41:49Speaker 00

  Yeah. Like, I want my pain to be admitted first. So if I notice that's coming up, I'll say it out loud.

• 41:54Simon Sinek?

  Yeah.

• 41:54Speaker 00

  I'll be like, I'm noticing right now that I want you to tell me that you messed up and to apologize first before I'm willing to apologize.

• 42:01Simon Sinek?

  Oh, I know.

• 42:02Speaker 00

  Even though I also am sorry.

• 42:02Simon Sinek?

  Oh, I don't do that.

• 42:03Speaker 00

  Yeah.

• 42:04Simon Sinek?

  I don't do that one.

• 42:05Speaker 00

  Yeah.

• 42:05Simon Sinek?

  Yeah, no, no. I misspoke. I misspoke. That's not what I meant. And I'd like to, I'd like to take back that I said that I do that too, because I don't.

• 42:12Speaker 00

  Yeah, but like, if there's something that I notice is going to block me, I try to name it as soon as possible.

• 42:17Simon Sinek?

  Yeah, so good.

• 42:17Speaker 00

  So it doesn't block me. So it doesn't get in my way. I'm like constantly trying to calm myself out.

• 42:21Simon Sinek?

  And this is also the danger of what we're teaching here, right?

• 42:23Speaker 00

  Yeah.

• 42:23Simon Sinek?

  Which is, everything we're teaching here, all of the techniques in all of these episodes, and there is an element of performative and practice and intellectualizing what should be emotional and human experiences, because you're learning. And that's okay. If you never get past that, where it doesn't become innate and natural, and you move past the checklist performative, because you get good at it, right? Nobody thinks about pedaling when you get on a bicycle anymore. And so I think we have to give grace, that if you're trying these techniques out for the first time, it will be hyper-intellectualized. It will feel like a checklist. We're even giving it as a checklist. Mindset, timing, like, we're actually making it a checklist. And that's okay. And if you keep practicing at

• 43:08Simon Sinek?

  some point, like riding a bicycle, you'll just get on your bike and ride.

• 43:12Speaker 00

  Mm-hmm.

• 43:12Simon Sinek?

  So, give yourself grace if this is a new thing for you, and if you bumble and fumble it and forget some of the techniques, it's okay. But the most important thing is, you practice. You do it. You do it because you want to be good at having difficult conversations, not because, ugh, this is part of my job. I'm now a middle management. I have to have this, damn this. Like, you're not doing it because it's some sort of like, job requirement.

• 43:33Speaker 00

  Yeah.

• 43:34Simon Sinek?

  But rather, you really want to learn this technique because it makes you the leader you want to be, and it's good for you and it's good for the people on the receiving end.

• 43:40Speaker 00

  I agree. And I think if people can feel that you're trying your best.

• 43:43Simon Sinek?

  Yeah.

• 43:43Speaker 00

  Even if you don't get it right, if you're not perfect at it, they can still feel you doing it. And so I think that's the most important thing to remember. It's like, all of these techniques are just scaffolding to help you connect and understand and build that trust.

• 43:56Simon Sinek?

  And I think that's the perfect way to summarize and conclude what we're talking about, which is, though we're making this sound scientific, and there is science and technique behind it, at the end of the day, human beings are messy, human relationships are messy, difficult conversations are messy.

• 44:14Speaker 00

  Super messy.

• 44:14Simon Sinek?

  This process is messy. No two will ever go the same. Just because you nailed it in one doesn't mean it's going to go well in the next time, because there's another person involved. And the way you describe these things more as scaffolding, they're there to help prop up what you're attempting to do, but it has to stand on its own two legs. Like, these are here to support you, because that's what scaffolding is.

• 44:34Speaker 00

  I would say I'm consistently humbled by how hard, hard conversations are, which is such an obvious thing to say, but I've spent so many years of my life studying these things.

• 44:41Simon Sinek?

  And you still screwed up.

• 44:42Speaker 00

  And I screwed up all the time. I think humbling is the perfect word for it. The gap between what I know that I could be doing versus what I'm able to do in the heat of the moment when the stakes are high, it's so big. And so I'm just reminding myself that I'm on a continuous journey to become the person who can have these hard conversations with more fluidity and more heart and more compassion and more ability to understand. Like, they're muscles that I built. And so I offer myself not only grace in the heat of the moment, but also just like over the long-term horizon of, this is so hard.

• 45:13Simon Sinek?

  Yeah.

• 45:13Speaker 00

  And it can be a little bit easier.

• 45:15Simon Sinek?

  And so where we're concluding is, you study this and teach this, and you're still, you're still learning.

• 45:20Speaker 00

  Oh my God, I have such, I have such a long way to go. It's crazy.

• 45:24Simon Sinek?

  Alex, we've had a very difficult conversation about difficult conversations. This has been really, really good.

• 45:29Speaker 00

  I think it's been fun.

• 45:30Simon Sinek?

  It was really good.

• 45:32Simon Sinek?

  A Bit of Optimism is a production of The Optimism Company. Lovingly produced by our team Lindsay Garbenius, Phoebe Bradford, and Devin Johnson. Subscribe wherever you enjoy listening to podcasts, and if you want even more cool stuff, visit simonsinek.com. Thanks for listening. Take care of yourself. Take care of each other.