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

1. 0:00 – 1:08

   Why We See Monsters Instead of People During Conflict

   1. ASAlex Simon0:00

      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.

   2. SSSimon Sinek0:16

      Wow.

   3. ASAlex Simon0:16

      So then we can both win.

   4. SSSimon Sinek0:17

      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.

   5. ASAlex Simon0:23

      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.

   6. SSSimon Sinek0:31

      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.

2. 1:08 – 2:16

   Hard Conversations Are Learnable Skills

   1. SSSimon Sinek1:08

      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.

3. 2:16 – 3:50

   Reframing Tension: It's a Sign, Not a Problem

   1. SSSimon Sinek2:16

      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.

4. 3:50 – 9:59

   The Resentment Gremlin: How We Feed Our Own Narratives

   1. ASAlex Simon3:50

      Today, we are talking about hard conversations.

   2. SSSimon Sinek3:52

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

   3. ASAlex Simon3:54

      You're right, let's just skip it. [laughs]

   4. SSSimon Sinek3:56

      [laughs]

   5. ASAlex Simon3:56

      It sounds hard.

   6. SSSimon Sinek3:57

      Sounds hard. No, it's too hard. Let's just-

   7. ASAlex Simon3:59

      [laughs]

   8. SSSimon Sinek3:59

      Let's just suppress everything and be passive aggressive-

   9. ASAlex Simon4:01

      Yes

   10. SSSimon Sinek4:01

       ... it's so much easier.

   11. ASAlex Simon4:02

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

   12. SSSimon Sinek4:04

       I don't want-

   13. ASAlex Simon4:04

       ... and then it'll go away

   14. SSSimon Sinek4:04

       ... 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.

   15. ASAlex Simon4:10

       [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."

   16. SSSimon Sinek4:25

       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.

   17. ASAlex Simon4:37

       Yeah.

   18. SSSimon Sinek4:37

       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.

   19. ASAlex Simon4:52

       Yeah.

   20. SSSimon Sinek4:52

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

   21. ASAlex Simon4:57

       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."

   22. SSSimon Sinek5:42

       Tension.

   23. ASAlex Simon5:43

       Yeah, yeah.

   24. SSSimon Sinek5:43

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

   25. ASAlex Simon5:47

       Yeah. [laughs]

   26. SSSimon Sinek5:48

       [laughs]

   27. ASAlex Simon5:48

       True.

   28. SSSimon Sinek5:49

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

   29. ASAlex Simon5:55

       Something's off.

   30. SSSimon Sinek5:56

       Right?
5. 9:59 – 11:15

   The Picture Frame Story: When Passive Aggression Becomes Comedy

   1. SSSimon Sinek9:59

      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.

   2. ASAlex Simon10:40

      For your sport. [laughs]

   3. SSSimon Sinek10:41

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

   4. ASAlex Simon10:44

      I wouldn't recommend best practice. [laughs]

   5. SSSimon Sinek10:46

      ... 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]

   6. ASAlex Simon10:58

      But things have changed.

   7. SSSimon Sinek10:59

      Well, I-

   8. ASAlex Simon10:59

      Now look at you. Look at where you are now. [laughs]

   9. SSSimon Sinek11:01

      Well, I have more skills. I'm not sure I have the maturity.

   10. ASAlex Simon11:02

       [laughs]

   11. SSSimon Sinek11:02

       So I mean like, you know, baby steps, baby steps, you know? [laughs] It was 20 years ago. [laughs]

   12. ASAlex Simon11:07

       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?

   13. SSSimon Sinek11:12

       There's a few things that get in the way of me having hard conversations.

6. 11:15 – 20:38

   What Actually Stops Us: Fear, Narrative Building, and Self-Righteousness

   1. SSSimon Sinek11:15

      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.

   2. ASAlex Simon11:21

      Mm-hmm.

   3. SSSimon Sinek11:21

      So I think we avoid difficult conversations. Fear as we talked about, like not wanting to trigger somebody.

   4. ASAlex Simon11:26

      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.

   5. SSSimon Sinek11:31

      Yes. That's the person on the receiving end-

   6. ASAlex Simon11:34

      Yeah

   7. SSSimon Sinek11:34

      ... 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.

   8. ASAlex Simon11:43

      Yeah.

   9. SSSimon Sinek11:43

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

   10. ASAlex Simon11:46

       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-

   11. SSSimon Sinek12:11

       Mm

   12. ASAlex Simon12:11

       ... not that considerate or they are not thinking about this.

   13. SSSimon Sinek12:13

       So the longer you wait-

   14. ASAlex Simon12:14

       The longer you wait

   15. SSSimon Sinek12:14

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

   16. ASAlex Simon12:17

       Yeah. And you're like accumulating your own proof points.

   17. SSSimon Sinek12:20

       Oh, yeah.

   18. ASAlex Simon12:20

       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."

   19. SSSimon Sinek12:26

       Yeah.

   20. ASAlex Simon12:26

       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.

   21. SSSimon Sinek12:38

       Oh, that's an uncomfortable one because I think we've all done that professionally, we've all done it personally-

   22. ASAlex Simon12:42

       Yeah

   23. SSSimon Sinek12:42

       ... 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-

   24. ASAlex Simon12:51

       Yeah

   25. SSSimon Sinek12:51

       ... and find all the proof points to prove, to prove yourself right.

   26. ASAlex Simon12:53

       Yeah.

   27. SSSimon Sinek12:53

       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.

   28. ASAlex Simon13:09

       Mm.

   29. SSSimon Sinek13:09

       So I don't wanna risk that.

   30. ASAlex Simon13:10

       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-
7. 20:38 – 26:27

   Conflict Is a Team Sport for Mutual Understanding

   1. SSSimon Sinek20:38

      conversation?

   2. ASAlex Simon20:38

      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.

   3. SSSimon Sinek20:48

      Let's say that again. Conflict is a team sport for mutual understanding.

   4. ASAlex Simon20:53

      Yeah.

   5. SSSimon Sinek20:53

      Break that down.

   6. ASAlex Simon20:53

      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.

   7. SSSimon Sinek21:31

      Inherent in the concept of conflict is that there's another person.

   8. ASAlex Simon21:34

      Yeah.

   9. SSSimon Sinek21:34

      So it recognizes that it's me and-

   10. ASAlex Simon21:36

       Yeah

   11. SSSimon Sinek21:37

       ... which I think is interesting.

   12. ASAlex Simon21:38

       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.

   13. SSSimon Sinek21:43

       Right.

   14. ASAlex Simon21:44

       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.

   15. SSSimon Sinek22:05

       Yeah.

   16. ASAlex Simon22:05

       So now we can both win.

   17. SSSimon Sinek22:06

       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.

   18. ASAlex Simon22:32

       Yeah.

   19. SSSimon Sinek22:33

       That's good. Keep going.

   20. ASAlex Simon22:34

       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.

   21. SSSimon Sinek22:42

       Yeah, we find a character flaw. They clearly don't have a capacity for dot, dot, dot.

   22. ASAlex Simon22:46

       Mm-hmm. Yeah. And we really believe that.

   23. SSSimon Sinek22:47

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

   24. ASAlex Simon22:53

       Yeah.

   25. SSSimon Sinek22:53

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

   26. ASAlex Simon22:57

       And we believe it-

   27. SSSimon Sinek22:58

       ... in this conversation

   28. ASAlex Simon22:58

       ... 'cause we've been accumulating the proof points

   29. SSSimon Sinek22:59

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

   30. ASAlex Simon23:03

       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?
8. 26:27 – 28:31

   Timing Matters: Not Too Hot, Not Too Cold

   1. ASAlex Simon26:27

      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-

   2. SSSimon Sinek26:49

      Yeah [laughs]

   3. ASAlex Simon26:49

      ... for me to understand this person-

   4. SSSimon Sinek26:50

      Yeah, exactly

   5. ASAlex Simon26:50

      ... who is also a monster," you know?

   6. SSSimon Sinek26:52

      Right.

   7. ASAlex Simon26:52

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

   8. SSSimon Sinek26:56

      Right.

   9. ASAlex Simon26:56

      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-

   10. SSSimon Sinek27:08

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

   11. ASAlex Simon27:12

       Exactly.

   12. SSSimon Sinek27:13

       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.

   13. ASAlex Simon27:19

       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.

   14. SSSimon Sinek27:24

       So the point is middle.

   15. ASAlex Simon27:26

       In the middle, yeah.

   16. SSSimon Sinek27:27

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

   17. ASAlex Simon27:31

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

   18. SSSimon Sinek27:35

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

   19. ASAlex Simon27:38

       Yeah, I won't show up hot, and it's still alive.

   20. SSSimon Sinek27:41

       Right.

   21. ASAlex Simon27:41

       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.

   22. SSSimon Sinek27:52

       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]

   23. ASAlex Simon27:59

       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-

   24. SSSimon Sinek28:04

       Right

   25. ASAlex Simon28:04

       ... conditions for it to go as well as possible.

   26. SSSimon Sinek28:06

       Okay.

   27. ASAlex Simon28:06

       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.

   28. SSSimon Sinek28:18

       That's the passive aggressive.

   29. ASAlex Simon28:19

       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-"

   30. SSSimon Sinek28:26

       Can we do it in a couple days?
9. 28:31 – 29:45

   Setting Your Intention: What Do You Actually Want?

   1. ASAlex Simon28:31

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

   2. SSSimon Sinek28:34

      Like I'm looking to feel heard, I'm looking for resolution, I'm looking for action, I'm looking to-

   3. ASAlex Simon28:38

      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."

   4. SSSimon Sinek28:44

      That's great.

   5. ASAlex Simon28:44

      So it's both coming back to my intention and maybe to our shared intention.

   6. SSSimon Sinek28:47

      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.

   7. ASAlex Simon28:52

      Yeah.

   8. SSSimon Sinek28:52

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

   9. ASAlex Simon28:55

      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."

   10. SSSimon Sinek29:04

       Right.

   11. ASAlex Simon29:04

       '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.

   12. SSSimon Sinek29:15

       Right.

   13. ASAlex Simon29:15

       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."

   14. SSSimon Sinek29:28

       Yeah.

   15. ASAlex Simon29:28

       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-

   16. SSSimon Sinek29:39

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

10. 29:45 – 32:36

    Asking for Grace: The Setup That Changes Everything

    1. ASAlex Simon29:45

       Yeah, tell me.

    2. SSSimon Sinek29:45

       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.

    3. ASAlex Simon29:55

       Mm.

    4. SSSimon Sinek29:55

       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.

    5. ASAlex Simon30:07

       Yeah.

    6. SSSimon Sinek30:07

       Like, the timing might be great for me-

    7. ASAlex Simon30:09

       But it might not be for them

    8. SSSimon Sinek30:10

       ... but it may not be great for them.

    9. ASAlex Simon30:10

       Yeah.

    10. SSSimon Sinek30:10

        So I need to have a difficult conversation. Can we have it now?

    11. ASAlex Simon30:14

        Yeah.

    12. SSSimon Sinek30:14

        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.

    13. ASAlex Simon30:36

        Yeah.

    14. SSSimon Sinek30:36

        "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."

    15. ASAlex Simon31:00

        Mm.

    16. SSSimon Sinek31:01

        "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."

    17. ASAlex Simon31:39

        Yeah.

    18. SSSimon Sinek31:39

        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."

    19. ASAlex Simon31:46

        Mm-hmm.

    20. SSSimon Sinek31:47

        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.

    21. ASAlex Simon32:01

        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."

    22. SSSimon Sinek32:10

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

    23. ASAlex Simon32:12

        Yeah.

    24. SSSimon Sinek32:12

        Like, it is so much easier for me not to do this.

    25. ASAlex Simon32:15

        Mm-hmm.

    26. SSSimon Sinek32:15

        I can just ignore it. That would be the better option for me.

    27. ASAlex Simon32:17

        Yeah.

    28. SSSimon Sinek32:17

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

    29. ASAlex Simon32:20

        And I'm willing to take the short-term discomfort over-

    30. SSSimon Sinek32:22

        Over long-term discomfort.
11. 32:36 – 38:02

    How to "Water Someone's Flowers"

    1. ASAlex Simon32:36

       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-

    2. SSSimon Sinek32:40

       Do you speak French?

    3. ASAlex Simon32:41

       N- no. It was [laughs] no, it's mostly in English and in Vietnamese.

    4. SSSimon Sinek32:45

       Okay.

    5. ASAlex Simon32:45

       [laughs] Which I also don't speak. They have-

    6. SSSimon Sinek32:46

       Was there wine? That's all that matters.

    7. ASAlex Simon32:48

       Absolutely not.

    8. SSSimon Sinek32:48

       Oh. What?

    9. ASAlex Simon32:49

       And it's in Bordeaux. [laughs]

    10. SSSimon Sinek32:50

        Come on.

    11. ASAlex Simon32:51

        No wine. No, a monastery.

    12. SSSimon Sinek32:51

        What a waste.

    13. ASAlex Simon32:53

        It's a monastery.

    14. SSSimon Sinek32:53

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

    15. ASAlex Simon32:55

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

    16. SSSimon Sinek32:58

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

    17. ASAlex Simon33:00

        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.

    18. SSSimon Sinek33:14

        Go on.

    19. ASAlex Simon33:14

        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]

    20. SSSimon Sinek33:32

        'Cause there's nothing good.

    21. ASAlex Simon33:33

        There's nothing good about them.

    22. SSSimon Sinek33:33

        Clearly.

    23. ASAlex Simon33:34

        Yeah.

    24. SSSimon Sinek33:34

        I like your hair. [laughs]

    25. ASAlex Simon33:36

        [laughs] That, that, okay, that's actually a great example.

    26. SSSimon Sinek33:38

        [laughs]

    27. ASAlex Simon33:38

        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]

    28. SSSimon Sinek34:06

        [laughs] I like-

    29. ASAlex Simon34:07

        Guys

    30. SSSimon Sinek34:07

        ... I like your hair. [laughs]
12. 38:02 – 39:55

    Try This Instead of Feedback Sandwiches

    1. SSSimon Sinek38:02

       I hate feedback sandwiches.

    2. ASAlex Simon38:04

       Yeah.

    3. SSSimon Sinek38:04

       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.

    4. ASAlex Simon38:32

       Yeah.

    5. SSSimon Sinek38:33

       And I think it has to be genuine.

    6. ASAlex Simon38:35

       Yeah.

    7. SSSimon Sinek38:36

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

    8. ASAlex Simon38:41

       Yeah

    9. SSSimon Sinek38:41

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

    10. ASAlex Simon38:48

        Yeah.

    11. SSSimon Sinek38:49

        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.

    12. ASAlex Simon39:00

        It has to be also real.

    13. SSSimon Sinek39:01

        It has to be real.

    14. ASAlex Simon39:01

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

    15. SSSimon Sinek39:04

        It's not a tactical thing.

    16. ASAlex Simon39:05

        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.

    17. SSSimon Sinek39:10

        Right.

    18. ASAlex Simon39:10

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

    19. SSSimon Sinek39:15

        Yeah. I'll give you an example how it could work with me, right?

    20. ASAlex Simon39:18

        Yeah.

    21. SSSimon Sinek39:18

        "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."

    22. ASAlex Simon39:29

        Mm-hmm.

    23. SSSimon Sinek39:30

        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.

    24. ASAlex Simon39:41

        And it's authentic.

    25. SSSimon Sinek39:42

        And it's authentic.

    26. ASAlex Simon39:43

        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,

13. 39:55 – 43:13

    Breaking the Fourth Wall: Pausing When Things Go Sideways

    1. ASAlex Simon39:55

       it won't do anything.

    2. SSSimon Sinek39:55

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

    3. ASAlex Simon39:57

       Yeah

    4. SSSimon Sinek39:58

       ... 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-

    5. ASAlex Simon40:04

       Yeah

    6. SSSimon Sinek40:05

       ... "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-

    7. ASAlex Simon40:28

       Yeah

    8. SSSimon Sinek40:29

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

    9. ASAlex Simon40:34

       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?"

    10. SSSimon Sinek40:51

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

    11. ASAlex Simon40:54

        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.

    12. SSSimon Sinek41:03

        We double down.

    13. ASAlex Simon41:04

        We double down. [laughs]

    14. SSSimon Sinek41:04

        'Cause, 'cause we'd rather, we'd rather not be wrong-

    15. ASAlex Simon41:06

        Than, than-

    16. SSSimon Sinek41:07

        ... than take it back.

    17. ASAlex Simon41:08

        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.

    18. SSSimon Sinek41:21

        Yeah.

    19. ASAlex Simon41:21

        But it kind of proves your point.

    20. SSSimon Sinek41:22

        Yeah.

    21. ASAlex Simon41:23

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

    22. SSSimon Sinek41:26

        Yeah.

    23. ASAlex Simon41:26

        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."

    24. SSSimon Sinek41:32

        Yeah.

    25. ASAlex Simon41:32

        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-

    26. SSSimon Sinek41:46

        Yeah

    27. ASAlex Simon41:47

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

    28. SSSimon Sinek41:49

        I, I, I'm like that. Yeah.

    29. ASAlex Simon41:50

        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.

    30. SSSimon Sinek41:54

        Yeah.
14. 43:13 – 45:51

    The Scaffolding, Not the Building: Embracing the Mess

    1. SSSimon Sinek43:13

       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.

    2. ASAlex Simon43:33

       Yeah.

    3. SSSimon Sinek43:34

       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.

    4. ASAlex Simon43:40

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

    5. SSSimon Sinek43:43

       Yeah

    6. ASAlex Simon43:43

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

    7. SSSimon Sinek43:48

       Yeah

    8. ASAlex Simon43:49

       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

    9. SSSimon Sinek43:56

       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

    10. ASAlex Simon44:14

        Super messy

    11. SSSimon Sinek44:14

        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-

    12. ASAlex Simon44:32

        Yeah

    13. SSSimon Sinek44:33

        ... 'cause that's what scaffolding is

    14. ASAlex Simon44:34

        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-

    15. SSSimon Sinek44:41

        And you still screw it up

    16. ASAlex Simon44:42

        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.

    17. SSSimon Sinek45:13

        Yeah

    18. ASAlex Simon45:13

        And it can be a little bit easier

    19. SSSimon Sinek45:15

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

    20. ASAlex Simon45:20

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

    21. SSSimon Sinek45:24

        Alex, we've had a very difficult conversation about difficult conversations.

    22. ASAlex Simon45:28

        [laughs]

    23. SSSimon Sinek45:28

        This has been really, really good

    24. ASAlex Simon45:29

        I think it's been fun [laughs]

    25. SSSimon Sinek45:30

        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.

Episode duration: 45:52