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

Alex Simon 0:00 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.

Simon Sinek 0:16 Wow.

Alex Simon 0:16 So then we can both win.

Simon Sinek 0:17 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.

Alex Simon 0:23 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.

Simon Sinek 0:31 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.

Simon Sinek 1:08 The reason this scenario is familiar is because most of us just plain suck at having difficult conversations. 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 LifeShop, 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, 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.

Simon Sinek 2:16 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. 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. 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 enjoy this episode, please remember to subscribe. This is A Bit of Optimism.

Alex Simon 3:50 Today, we are talking about hard conversations.

Simon Sinek 3:52 Oh, no, I don't want to talk about, have a hard conversation.

Alex Simon 3:54 You're right, let's just skip it. [laughs]

Simon Sinek 3:56 [laughs]

Alex Simon 3:56 It sounds hard.

Simon Sinek 3:57 Sounds hard. No, it's too hard. Let's just-

Alex Simon 3:59 [laughs]

Simon Sinek 3:59 Let's just suppress everything and be passive aggressive-

Alex Simon 4:01 Yes

Simon Sinek 4:01 ... it's so much easier.

Alex Simon 4:02 Yeah, let's pretend like nothing bad is happening-

Simon Sinek 4:04 I don't want-

Alex Simon 4:04 ... and then it'll go away

Simon Sinek 4:04 ... I wanna pretend there's nothing bad and there's no tension and everything's perfect. I don't wanna have a hard conversation. I think that's most people at work.

Alex Simon 4:10 [laughs] 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."

Simon Sinek 4:25 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 under- and holding space for other people. Why? 'Cause we want the romantic relationship to succeed.

Alex Simon 4:37 Yeah.

Simon Sinek 4:37 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 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.

Alex Simon 4:52 Yeah.

Simon Sinek 4:52 What are the circumstances? Why would we need to have a difficult conversation at work?

Alex Simon 4:57 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 at 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. It's the thing that surfaces, "Oh, there's something that needs to be addressed."

Simon Sinek 5:42 Tension.

Alex Simon 5:43 Yeah, yeah.

Simon Sinek 5:43 And it's really funny. The funny thing about tension is it's pretty much impossible for only one person to feel it.

Alex Simon 5:47 Yeah. [laughs]

Simon Sinek 5:48 [laughs]

Alex Simon 5:48 True.

Simon Sinek 5:49 Like, if one person feels tension in a relationship, I can almost guarantee the other person at least can assess something's off.

Alex Simon 5:55 Something's off.

Simon Sinek 5:56 Right?

Alex Simon 5:56 Yeah.

Simon Sinek 5:56 Like, tension is not something that one person has.

Alex Simon 5:58 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."

Simon Sinek 6:08 Right.

Alex Simon 6:08 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 [laughs] and 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."

Simon Sinek 6:20 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.

Alex Simon 6:49 Mm.

Simon Sinek 6:50 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, 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.

Alex Simon 7:15 Yeah. I think hard conversations are so hard that they intimidate us into not having them.

Simon Sinek 7:20 Yeah.

Alex Simon 7:20 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-

Simon Sinek 7:33 Right

Alex Simon 7:33 ... for me it ends up being more like preventative care. Like you have more smaller hard conversations.

Simon Sinek 7:38 Yeah.

Alex Simon 7:39 And then it feels more like communication. It feels more like you're like clearing the pathways.

Simon Sinek 7:42 Communication is lubrication, right? And the inability to communicate creates, you know, grinding and tension and stress and strain. I firmly believe that in, in any organization, the better you are communicating, the more lubricated the machine.

Alex Simon 7:54 Mm-hmm.

Simon Sinek 7:55 Let's just go through some of the circumstances under which this skill would be applicable. Obviously there are personality challenges. You know, we, we don't get along with everybody all the time.

Alex Simon 8:05 Mm-hmm.

Simon Sinek 8:05 Um, 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.

Alex Simon 8:14 Mm-hmm.

Simon Sinek 8:15 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 that the whole corporate culture of tens of thousands of people was passive aggressive.

Alex Simon 8:30 Yeah.

Simon Sinek 8:30 Because nobody ever got hard feedback.

Alex Simon 8:33 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, it's 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 pa- passive aggressive 'cause 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.

Simon Sinek 9:06 Right.

Alex Simon 9:06 [laughs] And then it would be crazy for you to be like, "Um, excuse me, Alex, normally you would've laughed at my joke." [laughs]

Simon Sinek 9:12 Right.

Alex Simon 9:12 You can't do that.

Simon Sinek 9:13 So I tiptoe around going, "I know something's wrong."

Alex Simon 9:16 Yeah.

Simon Sinek 9:16 I can't be like, "What's wrong?"

Alex Simon 9:19 Yeah.

Simon Sinek 9:19 Because you go, "Nothing's wrong."

Alex Simon 9:20 What are you talking about?

Simon Sinek 9:20 What are you talking about?

Alex Simon 9:21 Yeah.

Simon Sinek 9:21 Well, I made a joke and you didn't laugh at it. Well, maybe your joke wasn't funny.

Alex Simon 9:24 Yeah.

Simon Sinek 9:25 This may be a personality flaw, it may be an asset, I don't know.

Alex Simon 9:28 [laughs] We'll find out.

Simon Sinek 9:28 But I think, but 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 m- my part of the office. Didn't hang it up high on the wall, hang 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?

Simon Sinek 9:59 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." [laughs] Then he'd go back and I'm giggling and like having a blast because just come up to me and be like, "Hey Simon, we got an aesthetic here. You know, I know you wanna 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.

Alex Simon 10:40 For your sport. [laughs]

Simon Sinek 10:41 For my, for my sport. And I'm fully aware, not a good way to build a relationship-

Alex Simon 10:44 I wouldn't recommend best practice. [laughs]

Simon Sinek 10:46 ... 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. [laughs]

Alex Simon 10:58 But things have changed.

Simon Sinek 10:59 Well, I-

Alex Simon 10:59 Now look at you. Look at where you are now. [laughs]

Simon Sinek 11:01 Well, I have more skills. I'm not sure I have the maturity.

Alex Simon 11:02 [laughs]

Simon Sinek 11:02 So I mean like, you know, baby steps, baby steps, you know? [laughs] It was 20 years ago. [laughs]

Alex Simon 11:07 Okay. I'm curious, other than passive aggression, what are other things you notice for yourself that get in the way of, of having hard conversations?

Simon Sinek 11:12 There's a few things that get in the way of me having hard conversations.

Simon Sinek 11:15 Obviously you don't wanna hurt somebody's feelings, especially if you know somebody's sensitive. You, you don't want to hurt somebody, you wanna make them upset.

Alex Simon 11:21 Mm-hmm.

Simon Sinek 11:21 So I think we avoid difficult conversations. Fear as we talked about, like not wanting to trigger somebody.

Alex Simon 11:26 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.

Simon Sinek 11:31 Yes. That's the person on the receiving end-

Alex Simon 11:34 Yeah

Simon Sinek 11:34 ... 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 wanna know these things," but we don't know that.

Alex Simon 11:43 Yeah.

Simon Sinek 11:43 So I think that's part of it. You know, we don't wanna hurt somebody's feelings.

Alex Simon 11:46 Yeah. For me, one of the things that stops me from having hard conversations is believing my own story of them. Like I think that 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, you kind of think to yourself, "Okay, well it's a little frustrating that they're doing this." And then they do it a little bit more and I kind of think that they are this way, like they are lazier or they are-

Simon Sinek 12:11 Mm

Alex Simon 12:11 ... not that considerate or they are not thinking about this.

Simon Sinek 12:13 So the longer you wait-

Alex Simon 12:14 The longer you wait

Simon Sinek 12:14 ... you, you, you build up a worse and worse narrative of the other person.

Alex Simon 12:17 Yeah. And you're like accumulating your own proof points.

Simon Sinek 12:20 Oh, yeah.

Alex Simon 12:20 You know? And so then it goes from, "Oh, this thing happened once or a couple times" to "This person is this way. I don't trust them. I don't wanna work with them."

Simon Sinek 12:26 Yeah.

Alex Simon 12:26 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, uh, faith you have in their capacity to change.

Simon Sinek 12:38 Oh, that's an uncomfortable one because I think we've all done that professionally, we've all done it personally-

Alex Simon 12:42 Yeah

Simon Sinek 12:42 ... where a, a tension arises and reasonably quickly the snowball You know, builds to the point where you have completely assessed and judged their character-

Alex Simon 12:51 Yeah

Simon Sinek 12:51 ... and find all the proof points to prove, to prove yourself right.

Alex Simon 12:53 Yeah.

Simon Sinek 12:53 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.

Alex Simon 13:09 Mm.

Simon Sinek 13:09 So I don't wanna risk that.

Alex Simon 13:10 I feel like there's, like, a, 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-

Simon Sinek 13:19 Yeah

Alex Simon 13:19 ... wouldn't be able to go on. And so I would rather, like you said, like, live in this weakened version of a relationship-

Simon Sinek 13:24 Yeah

Alex Simon 13:24 ... 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.

Simon Sinek 13:29 Yeah. 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 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.

Alex Simon 13:58 Mm.

Simon Sinek 13:59 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 d- uncomfortable conversation, I'm basically accepting the loss of this relationship.

Alex Simon 14:14 Mm.

Simon Sinek 14:14 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.

Alex Simon 14:21 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.

Simon Sinek 14:29 Well, it was worse than that.

Alex Simon 14:30 Mm.

Simon Sinek 14:30 I was made to feel wrong.

Alex Simon 14:32 Mm.

Simon Sinek 14:33 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.

Alex Simon 14:56 Mm.

Simon Sinek 14:57 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.

Alex Simon 15:09 Mm-hmm.

Simon Sinek 15:10 Or the other s- thing is just who cares? Just move on.

Alex Simon 15:15 Well, I think it depends on what kind of who cares.

Simon Sinek 15:16 Depends, depends on-

Alex Simon 15:16 Yeah

Simon Sinek 15:17 ... depends, depends on how much I value the relationship, right?

Alex Simon 15:18 There's the, 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-

Simon Sinek 15:25 Yeah

Alex Simon 15:25 ... not everything's gonna be exactly how I want it to be. And I think it really depends. I find it to be a, a really intense tragedy when I lower the ceiling of what I think-

Simon Sinek 15:34 Yeah

Alex Simon 15:34 ... a friendship or a relationship or a work collaboration is, is capable of. I wanna go to some of the other things that I think stop 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.

Simon Sinek 15:51 Ugh, totally relate.

Alex Simon 15:52 Like, I feel morally superior.

Simon Sinek 15:54 Totally, totally relate.

Alex Simon 15:56 Yeah.

Simon Sinek 15:56 And I know they feel the same way.

Alex Simon 15:58 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... [growls]

Simon Sinek 16:05 [laughs]

Alex Simon 16:05 And, like, every time I, like, collect something [laughs] that someone else is doing wrong, I'm, like, feeding her. I'm like, "Here, take a cookie." You know? [laughs]

Simon Sinek 16:12 [laughs]

Alex Simon 16:12 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 that I'm choosing not to bring it up.

Simon Sinek 16:24 Oh, it's so good.

Alex Simon 16:24 I'm choosing not to bring it up every single time.

Simon Sinek 16:25 So good.

Alex Simon 16:26 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 these things.

Simon Sinek 16:39 [laughs]

Alex Simon 16:39 Like, there's... When I zoom out, I think what I'm doing in those situations is picking my, like, short-term satisfaction over the relationship in the long term.

Simon Sinek 16:50 But you said it right, which is that resentment gremlin is a self-righteousness.

Alex Simon 16:54 Yeah.

Simon Sinek 16:54 Which is if I can feed the resentment gremlin, then I can feel right.

Alex Simon 17:01 Yeah.

Simon Sinek 17:01 And that helps me manage the tension, the discomfort, the anger, and the frustration because at least I'm on the side of right.

Alex Simon 17:07 Totally.

Simon Sinek 17:08 You know?

Alex Simon 17:08 Yeah.

Simon Sinek 17:09 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. [laughs]

Alex Simon 17:16 Yeah, which is way less fun. [laughs]

Simon Sinek 17:17 Which is way less fun for him. [laughs]

Alex Simon 17:19 Yeah. 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.

Simon Sinek 17:29 Mm.

Alex Simon 17:29 I wanna prove to you why you're wrong, and I wanna prove to you why I'm right. I wanna win the c- 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?

Simon Sinek 17:41 I wanna 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.

Alex Simon 17:49 Yeah.

Simon Sinek 17:49 So for example, sometimes asking somebody for a raise can be excruciating and excessive planning and, and stress-causing. But sometimes you have to have that conversation.

Alex Simon 17:59 Yeah.

Simon Sinek 17:59 And it doesn't mean anything bad has happened or, you know, your boss is a bad person or anything like that. It just means the conversation needs to happen.

Alex Simon 18:05 Yeah.

Simon Sinek 18:05 Or you feel like you're capable of more, or you wanna redirect your career, or you're not enjoying this part of the job and you wanna 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's gonna be. We don't wanna piss somebody off. We don't wanna get it wrong. We create stakes that there may or may not be there.

Alex Simon 18:22 Yeah.

Simon Sinek 18:22 And I just wanna 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.

Alex Simon 18:31 Yeah. And I think that's the most important point is like it's normal, it's going to happen.

Simon Sinek 18:36 It's, they have to happen.

Alex Simon 18:37 They have to happen.

Simon Sinek 18:38 If you feel like you need-

Alex Simon 18:39 Yeah

Simon Sinek 18:39 ... a raise or you wanna try a different job and you never self-advocate, then you're gonna sit there resentful that the company doesn't appreciate you, your boss doesn't appreciate you, and then the, you feed the resentment gremlin-

Alex Simon 18:48 Yeah

Simon Sinek 18:48 ... and you start resenting the person or the company simply-

Alex Simon 18:50 When you haven't done anything-

Simon Sinek 18:51 When-

Alex Simon 18:51 ... to even make a change

Simon Sinek 18:52 ... when-

Alex Simon 18:52 Yeah

Simon Sinek 18:52 ... when you haven't leaned into your ability to have that difficult conversation.

Alex Simon 18:56 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.

Simon Sinek 19:04 Yeah.

Alex Simon 19:04 So instead of laying there at night lamenting the fact that the problem is ongoing, a- wh- while we're simultaneously not doing anything different to try to change it, when we realize, oh, this is just part of the process-

Simon Sinek 19:15 Yeah

Alex Simon 19:15 ... 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?

Simon Sinek 19:21 Yeah.

Alex Simon 19:22 And then we can actually engage with, okay, there are things that I can do to make this easier.

Simon Sinek 19:25 So this is a good segue.

Alex Simon 19:27 Yeah.

Simon Sinek 19:27 Now let's talk about how-

Alex Simon 19:28 How do we do it? [laughs]

Simon Sinek 19:28 ... how do we do it? Let's talk about how to have a hard conversation. The stuff that we're talking about here, and 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 are newly promoted to a position of leadership or you have to do y- 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-

Alex Simon 20:00 You don't say it

Simon Sinek 20:01 ... doesn't, doesn't land-

Alex Simon 20:01 Yeah

Simon Sinek 20:02 ... even though you know you have to communicate it, so you have to have the, the difficult conversation because it, it's my annual review and you gotta give me the, the news. But because we don't have the skills on how to have a difficult conversation, it becomes self-fulfilling.

Alex Simon 20:14 Mm-hmm.

Simon Sinek 20:14 It actually does become a mess because we don't know how to deliver the news. So I think the skill is, it, 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.

Alex Simon 20:27 Mm-hmm.

Simon Sinek 20:27 So it's just part of the job, and our companies don't teach us.

Alex Simon 20:30 No one teaches us.

Simon Sinek 20:30 No one teaches us.

Alex Simon 20:31 Yeah.

Simon Sinek 20:31 Ex- except for now.

Alex Simon 20:33 [laughs]

Simon Sinek 20:33 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

Simon Sinek 20:38 conversation?

Alex Simon 20:38 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.

Simon Sinek 20:48 Let's say that again. Conflict is a team sport for mutual understanding.

Alex Simon 20:53 Yeah.

Simon Sinek 20:53 Break that down.

Alex Simon 20:53 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 wanna 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.

Simon Sinek 21:31 Inherent in the concept of conflict is that there's another person.

Alex Simon 21:34 Yeah.

Simon Sinek 21:34 So it recognizes that it's me and-

Alex Simon 21:36 Yeah

Simon Sinek 21:37 ... which I think is interesting.

Alex Simon 21:38 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.

Simon Sinek 21:43 Right.

Alex Simon 21:44 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, wait, 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.

Simon Sinek 22:05 Yeah.

Alex Simon 22:05 So now we can both win.

Simon Sinek 22:06 That's 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.

Alex Simon 22:32 Yeah.

Simon Sinek 22:33 That's good. Keep going.

Alex Simon 22:34 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.

Simon Sinek 22:42 Yeah, we find a character flaw. They clearly don't have a capacity for dot, dot, dot.

Alex Simon 22:46 Mm-hmm. Yeah. And we really believe that.

Simon Sinek 22:47 I even just said it to you in, in recounting my experience. Like, they have no capacity for listening.

Alex Simon 22:53 Yeah.

Simon Sinek 22:53 They don't know how to hold space. They're always rational. I literally just did it-

Alex Simon 22:57 And we believe it-

Simon Sinek 22:58 ... in this conversation

Alex Simon 22:58 ... 'cause we've been accumulating the proof points

Simon Sinek 22:59 ... and I've, I've completely assessed their entire character based on one tension I'm sitting in.

Alex Simon 23:03 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 dealing with?

Simon Sinek 23:24 Like we are in tension. That is the problem.

Alex Simon 23:26 Yeah. There's something that's going on between us that we both don't fully understand that we can try to understand together.

Simon Sinek 23:31 Yeah.

Alex Simon 23:32 And it's, it's so beautiful. The image that always comes to me is it's 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 and the water can't flow, and we're just, like, sitting in that every single day.

Simon Sinek 23:44 Yeah.

Alex Simon 23:44 And so when we can understand each other and we can remove some of the, the blocks, things can naturally flow.

Simon Sinek 23:49 Yeah.

Alex Simon 23:49 And we're doing that at work all the time.

Simon Sinek 23:52 And we build narratives about each other.

Alex Simon 23:53 Yeah.

Simon Sinek 23:53 You know, m- m- 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 per- perpetuate those narratives. Ugh, the lazy one.

Alex Simon 24:08 Yeah.

Simon Sinek 24:08 Ugh, the stupid one.

Alex Simon 24:09 Yeah.

Simon Sinek 24:10 Ugh, the angry one. You know?

Alex Simon 24:10 And we triangulate with other people.

Simon Sinek 24:12 Yeah.

Alex Simon 24:12 I think this is another thing that happens a lot is, 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, "Ugh, can you believe Simon's doing this? Ugh, 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, 'cause the more other people I can get on my side, "Oh, yeah, he's the problem."

Simon Sinek 24:35 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.

Alex Simon 24:42 Wow.

Simon Sinek 24:42 And they said, "If you have a tension, you have to learn to lean into it with somebody-

Alex Simon 24:45 Mm-hmm

Simon Sinek 24:45 ... 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, "Ugh, 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 j- assessing their character.

Alex Simon 24:58 Yeah.

Simon Sinek 24:58 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. This 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-

Alex Simon 25:30 Mm-hmm

Simon Sinek 25:30 ... they're overwhelmed." And simply acknowledging that there are other possibilities that are creating that behavior makes everybody go, "Oh, yeah." 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.

Alex Simon 25:48 Yeah.

Simon Sinek 25:48 So that's been very, very helpful.

Alex Simon 25:50 Mm-hmm, 'cause, like, once one of those narratives gets planted and mutually agreed upon by everyone, it's so hard to unsilt that.

Simon Sinek 25:56 And that person is now playing defense for the rest of their job-

Alex Simon 25:59 Yeah

Simon Sinek 25:59 ... until they get forced out or, or quit.

Alex Simon 26:02 Yeah, and everyone loses.

Simon Sinek 26:03 Yeah.

Alex Simon 26:04 Like, it sucks for everyone.

Simon Sinek 26:05 It's a, it's a lose-lose. Yeah.

Alex Simon 26:06 Yeah.

Simon Sinek 26:06 Okay, so the first element of the difficult conversation is the mindset.

Alex Simon 26:09 Mm-hmm.

Simon Sinek 26:10 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, may- or more too, but the point is this isn't, 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?

Alex Simon 26:27 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 gonna be the situation in which you're gonna be able to have the most productive conflict. You're not gonna be able to be like, "Huh, conflict is a team sport for mutual understanding. What an excellent opportunity-

Simon Sinek 26:49 Yeah [laughs]

Alex Simon 26:49 ... for me to understand this person-

Simon Sinek 26:50 Yeah, exactly

Alex Simon 26:50 ... who is also a monster," you know?

Simon Sinek 26:52 Right.

Alex Simon 26:52 So I think you don't want it to be while, like, in the heat of the moment necessarily.

Simon Sinek 26:56 Right.

Alex Simon 26:56 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, and then-

Simon Sinek 27:08 Or they bring it up and create a tension that actually... Because it's still festering in their mind.

Alex Simon 27:12 Exactly.

Simon Sinek 27:13 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.

Alex Simon 27:19 So I think it depends on where you naturally are. Like, some people don't wait enough time, and some people wait too much time.

Simon Sinek 27:24 So the point is middle.

Alex Simon 27:26 In the middle, yeah.

Simon Sinek 27:27 Like, but just don't do it in the heat of the moment. Don't wait too long. Do it somewhere in between.

Alex Simon 27:31 So for me, I try to wait until it's no longer dysregulating my system.

Simon Sinek 27:35 So you're no longer angry, or rather you won't show up hot.

Alex Simon 27:38 Yeah, I won't show up hot, and it's still alive.

Simon Sinek 27:41 Right.

Alex Simon 27:41 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.

Simon Sinek 27:52 Y- 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. [laughs]

Alex Simon 27:59 Totally. [laughs] 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-

Simon Sinek 28:04 Right

Alex Simon 28:04 ... conditions for it to go as well as possible.

Simon Sinek 28:06 Okay.

Alex Simon 28:06 So it's like, "Okay, in this moment, I don't feel like I can listen to you, and I really wanna 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.

Simon Sinek 28:18 That's the passive aggressive.

Alex Simon 28:19 Yeah, and so I would say, "Yes, I wanna 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. I think-"

Simon Sinek 28:26 Can we do it in a couple days?

Alex Simon 28:27 Yeah.

Simon Sinek 28:28 So-

Alex Simon 28:28 Okay

Simon Sinek 28:28 ... mindset, timing.

Alex Simon 28:30 Mindset, timing.

Alex Simon 28:31 Another thing that I like to do is come back to my intention for the conflict.

Simon Sinek 28:34 Like I'm looking to feel heard, I'm looking for resolution, I'm looking for action, I'm looking to-

Alex Simon 28:38 Yeah. It's like, "Hey, I know that we both care about this thing. I wanna figure out a way to communicate about it so that we can get to this place that we wanna both be in."

Simon Sinek 28:44 That's great.

Alex Simon 28:44 So it's both coming back to my intention and maybe to our shared intention.

Simon Sinek 28:47 And s- and, and setting a goal, right? So knowing the reason you're going in, otherwise you're just coming in with the emotion.

Alex Simon 28:52 Yeah.

Simon Sinek 28:52 And there's no destination set for the path you're about to, to journey on.

Alex Simon 28:55 Exactly. And I... 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 wanna win. I wanna show why I'm right."

Simon Sinek 29:04 Right.

Alex Simon 29:04 '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.

Simon Sinek 29:15 Right.

Alex Simon 29:15 And that changes the frame. So that's the first thing that it does. And then the second thing is that I like to 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."

Simon Sinek 29:28 Yeah.

Alex Simon 29:28 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 wanna-

Simon Sinek 29:39 I wanna get to the goal. Mindset, timing, setting a goal. Can I... Here's something I do.

Alex Simon 29:45 Yeah, tell me.

Simon Sinek 29:45 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 I- what I've learned is otherwise you come in hot.

Alex Simon 29:55 Mm.

Simon Sinek 29:55 And even if you're, you aren't, that's how it's received, and you get very defensive responses. And so by preparing somebody that this is not gonna be fun, there's a beat that they can take a breath. And I ask permission 'cause, 'cause you know we talk about timing.

Alex Simon 30:07 Yeah.

Simon Sinek 30:07 Like, the timing might be great for me-

Alex Simon 30:09 But it might not be for them

Simon Sinek 30:10 ... but it may not be great for them.

Alex Simon 30:10 Yeah.

Simon Sinek 30:10 So I need to have a difficult conversation. Can we have it now?

Alex Simon 30:14 Yeah.

Simon Sinek 30:14 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, 'cause I also want them to show up 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.

Alex Simon 30:36 Yeah.

Simon Sinek 30:36 "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 where 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 wanna see you thrive here, I wanna see you do well, and I wanna be supportive of you, I have to have this conversation with you. I'm gonna get some things wrong."

Alex Simon 31:00 Mm.

Simon Sinek 31:01 "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 mis-frame something, say something unclearly, say something wrong, they will latch onto it, and n- n- now I'm playing defense. I'm like, "Well, that's not what I meant though." They're like, "Well then why are you telling me this?" And so it, 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."

Alex Simon 31:39 Yeah.

Simon Sinek 31:39 And they go, "Okay." Because they gave me permission at the beginning, and if they forget I'd be like, "You, you s- remember I said I'm gonna get some things wrong. Please."

Alex Simon 31:46 Mm-hmm.

Simon Sinek 31:47 You know? And so I help them get on the right mindset with me. I check in on their timing. I ask for grace, 'cause it is complicated and difficult, and i- I'm not an expert, but I need to do this. And I've found that that framing has been immensely helpful.

Alex Simon 32:01 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."

Simon Sinek 32:10 By the way, I'd rather not have this.

Alex Simon 32:12 Yeah.

Simon Sinek 32:12 Like, it is so much easier for me not to do this.

Alex Simon 32:15 Mm-hmm.

Simon Sinek 32:15 I can just ignore it. That would be the better option for me.

Alex Simon 32:17 Yeah.

Simon Sinek 32:17 But I'm doing this because I actually really care.

Alex Simon 32:20 And I'm willing to take the short-term discomfort over-

Simon Sinek 32:22 Over long-term discomfort.

Alex Simon 32:23 Yeah.

Simon Sinek 32:23 I'd rather have a lot of discomfort now rather than the slow drip of discomfort for a long period of time 'cause-

Alex Simon 32:29 Which is the opposite of what we want really

Simon Sinek 32:29 ... which is because that's actually more cancerous-

Alex Simon 32:32 Yeah

Simon Sinek 32:32 ... than, than what we're gonna deal with now.

Alex Simon 32:33 Okay, can I s- share kind of a crazy one?

Simon Sinek 32:35 Yeah.

Alex Simon 32:35 But it's

Alex Simon 32:36 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-

Simon Sinek 32:40 Do you speak French?

Alex Simon 32:41 N- no. It was [laughs] no, it's mostly in English and in Vietnamese.

Simon Sinek 32:45 Okay.

Alex Simon 32:45 [laughs] Which I also don't speak. They have-

Simon Sinek 32:46 Was there wine? That's all that matters.

Alex Simon 32:48 Absolutely not.

Simon Sinek 32:48 Oh. What?

Alex Simon 32:49 And it's in Bordeaux. [laughs]

Simon Sinek 32:50 Come on.

Alex Simon 32:51 No wine. No, a monastery.

Simon Sinek 32:51 What a waste.

Alex Simon 32:53 It's a monastery.

Simon Sinek 32:53 I mean, they're French monks though. French monks drink.

Alex Simon 32:55 No, they're Vietnamese. [laughs] And monks don't drink. [laughs]

Simon Sinek 32:58 I mean, what a tease to do it in Bordeaux.

Alex Simon 33:00 I know. Anyway, they have so much that they talk about about conflict 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.

Simon Sinek 33:14 Go on.

Alex Simon 33:14 But it sounds floofy. But basically one of the, their most magic tricks is called watering someone's flowers, which is the 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. [laughs]

Simon Sinek 33:32 'Cause there's nothing good.

Alex Simon 33:33 There's nothing good about them.

Simon Sinek 33:33 Clearly.

Alex Simon 33:34 Yeah.

Simon Sinek 33:34 I like your hair. [laughs]

Alex Simon 33:36 [laughs] That, that, okay, that's actually a great example.

Simon Sinek 33:38 [laughs]

Alex Simon 33:38 So for example, when I f- 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 [laughs] 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." [laughs]

Simon Sinek 34:06 [laughs] I like-

Alex Simon 34:07 Guys

Simon Sinek 34:07 ... I like your hair. [laughs]

Alex Simon 34:09 [laughs] And I looked at her, truly my favorite person on the planet, and I could not think of a single nice thing to say.

Simon Sinek 34:17 Oh, my goodness.

Alex Simon 34:18 And I was looking at her for an embarrassingly long amount of time.

Simon Sinek 34:20 Oh, my goodness.

Alex Simon 34:20 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.

Simon Sinek 34:29 Oh.

Alex Simon 34:29 And it was, like, more fact-based than anything.

Simon Sinek 34:30 Nice pants.

Alex Simon 34:31 Yeah.

Simon Sinek 34:32 [laughs]

Alex Simon 34:32 That, that kind of thing, like, I like this, whatever it was.

Simon Sinek 34:34 Those are great shoes. [laughs]

Alex Simon 34:35 [laughs] Totally. But I said it. And-

Simon Sinek 34:39 [laughs]

Alex Simon 34:39 ... 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.

Simon Sinek 34:48 And you're like, "They are good shoes." [laughs]

Alex Simon 34:50 [laughs] You're right, I do have good hair.

Simon Sinek 34:52 [laughs]

Alex Simon 34:53 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.

Simon Sinek 35:22 So here's what I'm hearing, right?

Alex Simon 35:24 Yeah.

Simon Sinek 35:24 And this is really important. So w- 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.

Alex Simon 35:32 Yeah.

Simon Sinek 35:33 And what I like here is about affirming the other person.

Alex Simon 35:35 Yeah.

Simon Sinek 35:35 Because conflict is hard, and for some, having, leaning into difficult 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, a, 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 floofy stuff-

Alex Simon 35:57 [laughs]

Simon Sinek 35:58 ... but I do like watering someone's flowers. I think that is actually a beautiful, uh, metaphor-

Alex Simon 36:01 Yeah

Simon Sinek 36:02 ... um, 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 this, 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.

Alex Simon 36:24 Mm-hmm. Yeah.

Simon Sinek 36:25 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.

Alex Simon 36:32 Yeah. And then it allows people to hear the things that are harder.

Simon Sinek 36:34 'Cause they recognize that you don't think I'm a dumbass.

Alex Simon 36:36 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-

Simon Sinek 36:51 Yeah

Alex Simon 36:51 ... of, like, all the other things that are actually going right.

Simon Sinek 36:53 Yeah.

Alex Simon 36:53 And often when we're having a hard conversation, we're only fixated on the ways in which things are going wrong. I wanna 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 'cause I think it just starts us off in a different place. What do I appreciate? What's working well? What do I wanna 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, 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 o- 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 kinda spontaneously be like, "Okay, well, I also just wanna honor that these are the, the other things that I appreciate about you."

Simon Sinek 37:59 Let me throw a s- a wrench in the works here.

Alex Simon 38:01 Throw a wrench.

Simon Sinek 38:02 I hate feedback sandwiches.

Alex Simon 38:04 Yeah.

Simon Sinek 38:04 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 f- find it very distracting.

Alex Simon 38:32 Yeah.

Simon Sinek 38:33 And I think it has to be genuine.

Alex Simon 38:35 Yeah.

Simon Sinek 38:36 'Cause if they say, "Well, Simon, you know, you're a good listener," I'm like, "Signifying nothing-

Alex Simon 38:41 Yeah

Simon Sinek 38:41 ... in this moment, we're talking about this. So thanks for the compliment, not interested." Like, that would probably be my, my [laughs] response.

Alex Simon 38:48 Yeah.

Simon Sinek 38:49 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.

Alex Simon 39:00 It has to be also real.

Simon Sinek 39:01 It has to be real.

Alex Simon 39:01 It's, it's not a tactical thing. It's not a box that you have to check.

Simon Sinek 39:04 It's not a tactical thing.

Alex Simon 39:05 It- that's also how I feel about the feedback sandwich is like normally it's just a box you have to check to get to the actual thing that you wanna say.

Simon Sinek 39:10 Right.

Alex Simon 39:10 Whereas this is like you're saying something real that wouldn't normally fit into your perspective in this moment.

Simon Sinek 39:15 Yeah. I'll give you an example how it could work with me, right?

Alex Simon 39:18 Yeah.

Simon Sinek 39:18 "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? 'Cause I know you're good at it."

Alex Simon 39:29 Mm-hmm.

Simon Sinek 39:30 So I'm like, "I am. Thank you very much," you know? That would be a, a, a relevant and good use of watering my flowers because it's relevant to what we're engaged in.

Alex Simon 39:41 And it's authentic.

Simon Sinek 39:42 And it's authentic.

Alex Simon 39:43 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,

Alex Simon 39:55 it won't do anything.

Simon Sinek 39:55 And I have one more thing to add to our checklist-

Alex Simon 39:57 Yeah

Simon Sinek 39:58 ... 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-

Alex Simon 40:04 Yeah

Simon Sinek 40:05 ... "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? 'Cause it's getting heated, and I just want you to know I..." And so you can interrupt and reset at any point-

Alex Simon 40:28 Yeah

Simon Sinek 40:29 ... and go back to any of the other things and sometimes even start again. Like, that works, too.

Alex Simon 40:34 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 gonna be productive for either one of us." I'll also personally ask for, like, a takeback. I'll be like, "I just said this, but actually I don't mean it. Can I please take it back?"

Simon Sinek 40:51 And because you asked for grace upfront, you're good to go. [laughs]

Alex Simon 40:54 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.

Simon Sinek 41:03 We double down.

Alex Simon 41:04 We double down. [laughs]

Simon Sinek 41:04 'Cause, 'cause we'd rather, we'd rather not be wrong-

Alex Simon 41:06 Than, than-

Simon Sinek 41:07 ... than take it back.

Alex Simon 41:08 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've 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.

Simon Sinek 41:21 Yeah.

Alex Simon 41:21 But it kind of proves your point.

Simon Sinek 41:22 Yeah.

Alex Simon 41:23 [laughs] So you double down on it, but you both know that that's not what they meant.

Simon Sinek 41:26 Yeah.

Alex Simon 41:26 But that's also about winning and, like, you versus me and not, "Hey, I wanna understand you, and, like, let's face the problem together."

Simon Sinek 41:32 Yeah.

Alex Simon 41:32 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'd messed something up-

Simon Sinek 41:46 Yeah

Alex Simon 41:47 ... before I'm willing to also admit that I've messed something up.

Simon Sinek 41:49 I, I, I'm like that. Yeah.

Alex Simon 41:50 Yeah. Like, I want my pain to be admit- admitted first. So s- if I notice that's coming up, I'll say it out loud.

Simon Sinek 41:54 Yeah.

Alex Simon 41:54 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-

Simon Sinek 42:01 Oh, I n-

Alex Simon 42:01 ... even though I also am sorry."

Simon Sinek 42:02 Oh, I don't do that.

Alex Simon 42:03 Yeah. [laughs]

Simon Sinek 42:04 I don't, I don't do that one.

Alex Simon 42:05 Yeah.

Simon Sinek 42:05 Yeah, no, no, I take it. I t- I misspoke. I misspoke. That's not what I meant.

Alex Simon 42:09 All applause.

Simon Sinek 42:09 And I'd like to, I'd like to take back that I said that I do that too, 'cause I don't. [laughs]

Alex Simon 42:12 Yeah. But, like, if there's something that I notice is gonna block me, I try to name it as soon as possible-

Simon Sinek 42:17 Yeah, it's so good

Alex Simon 42:17 ... so it doesn't block me.

Simon Sinek 42:18 Yeah.

Alex Simon 42:18 So it doesn't get in my way. I'm, like, constantly trying to call myself out.

Simon Sinek 42:21 And this is also the danger of what we're teaching here, right?

Alex Simon 42:23 Yeah.

Simon Sinek 42:23 Which is everything we're teaching here, y- 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, 'cause you get good at it, right? Nobody thinks about pedaling when you get on a bicycle anymore.

Alex Simon 42:53 Mm.

Simon Sinek 42:53 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 a- we're actually making it a checklist, and that's okay. And if you keep practicing, at some point, like riding a bicycle, you'll just get on your bike and ride.

Alex Simon 43:12 Mm-hmm.

Simon Sinek 43:12 So

Simon Sinek 43:13 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 middle management. I have to have this, damn this. Like, you're not doing it because it's some sort of, like, job requirement.

Alex Simon 43:33 Yeah.

Simon Sinek 43:34 But rather you really want to learn this technique because it makes you the leader you wanna be, and it's good for you, and it's good for the people on the receiving end.

Alex Simon 43:40 I agree. And I think if people can feel that you're trying your best-

Simon Sinek 43:43 Yeah

Alex Simon 43:43 ... even if you don't Get it right. Even if you're not perfect at it, they can still feel you doing it

Simon Sinek 43:48 Yeah

Alex Simon 43:49 And so I think that's the most important thing to remember is like all of these techniques are just scaffolding to help you connect and understand and build that trust

Simon Sinek 43:56 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

Alex Simon 44:14 Super messy

Simon Sinek 44:14 This process is messy. No two will ever go the same. Just 'cause you nailed it in one doesn't mean it's gonna go well in the next time because there's another person involved. And the way you describe these things more as scaffolding, th- they're there to help prop up what you're attempting to do, but it has to stand on its own two legs. Like, it... These are here to support you-

Alex Simon 44:32 Yeah

Simon Sinek 44:33 ... 'cause that's what scaffolding is

Alex Simon 44:34 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 and now teaching-

Simon Sinek 44:41 And you still screw it up

Alex Simon 44:42 And I screw it 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 o- over the long term horizon of this is so hard.

Simon Sinek 45:13 Yeah

Alex Simon 45:13 And it can be a little bit easier

Simon Sinek 45:15 And so where we're concluding is you study this and teach this, and you're still, you're still learning

Alex Simon 45:20 Oh my God, I have such, I have such a long way to go. It's crazy

Simon Sinek 45:24 Alex, we've had a very difficult conversation about difficult conversations.

Alex Simon 45:28 [laughs]

Simon Sinek 45:28 This has been really, really good

Alex Simon 45:29 I think it's been fun [laughs]

Simon Sinek 45:30 It was really good. As always, thank you for watching. If you liked this episode, please subscribe to A Bit of Optimism for more interesting guests and even more interesting conversations. New episodes drop every Tuesday. But if you'd like more optimism right now, click here to watch another episode. Until next time, take care of yourself, take care of each other.