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

Episode Date: August 11, 2026

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

When I'm in a really intense conflict with someone, maybe I care about them, maybe I have loved working with them. I can't see any of that. Like I see like a monster in front of me. When I'm able to relax that and be like, oh, you're not some evil being with bad intentions, but you're just a person who I seek to understand, who I want to help understand me. It changes everything. So we can both win. 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. 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 from mutual understanding. 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's, doesn't come out exactly like we rehearsed. We fumble our words, we say what we want to say in all the wrong ways. They get defensive and now it's even worse. Worse than if we had just said nothing. The reason this scenario is familiar is because most of us just plain suck at having difficult conversations. 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. 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. In 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. 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. Today we are talking about hard conversations. Oh, no, I don't want to talk about a hard conversation. You're right. Let's just skip it. It sounds hard. No, it's too hard.

Let's just suppress everything and be passive-aggressive. It's so much easier. Yeah, let's pretend like nothing bad is happening. I don't want to pretend there's nothing bad and there's no tension and everything's perfect. I don't want to have a hard conversation. I think that's most people at work. 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 were like, oh, marriage is hard. But we're not like, oh, my collaborative relationships with people will naturally have friction, that wouldn't be really hard to navigate, and I'm going to have to, like, muster emotional courage to do my job. You say this all the time, right? We understand that marriage is a relationship or relationships or relationships that we have to learn the emotional regulation and holding space for other people. Why? Because we want the romantic relationship to succeed. So we, quote,

unquote, do the work. We teach our kids how to manage their emotions and regulate their emotions so that they can have friends and be functional members of a society. But we don't talk about this stuff at work. And one of the big gaping holes at work is the ability to have to be able to have to be friends. difficult conversation. What are the circumstances? Why would we need to have a difficult conversation at work? 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 my brain that would be like, ah, pain, pain, 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. Yeah. And it's really funny. The funny thing about tension is it's pretty much impossible for only one person to feel it. Yeah, sure. Like, if one person feels tension in a relationship,

I can almost guarantee the other person at least can assess something's off. Something's off. Right? Yeah. Like, tension is not something that one person has. 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 going to go away on its own, right? Even though we have the lived experience over and over and over again of, oh, it doesn't go away at its own. And in fact, it gets exacerbated and it gets so much worse. Still, we, we for some reason believe, if I don't address it, it won't be real and it'll kind of solve itself. 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 are like really good leaders. Like people who, like they know the skills, they do the work, said nothing. They didn't address it. And the reason was they were so afraid of getting it wrong. They were so afraid of triggering somebody by accident. They were so afraid of not being perfect that they chose to say nothing. And that's when I realized, oh my goodness, these are good people who lack a skill and out of fear or concern

chose probably the worst scenario, 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.

Yeah, I think hard conversations are so hard that they intimidate us into not having them. Yeah. And then what happens is that they kind of fester. And then by the time we have to bring them up, but they've exploded. They're like way more intense than they needed to be. Whereas if we were able to have hard conversations, to your point, if we had the skills to have the hard conversations, for me, it ends up being more like preventative care. Like you have more smaller hard conversations.

And then it feels more like communication. It feels more like you're like clearing the pathways. Communication is lubrication, right? And the inability to communicate creates, you know, grinding and tension and stress and strain. I firmly believe that in any organization, the better you are communicating, the more lubricated the machine. Let's just go through some of the circumstances under which the skill would be applicable. Obviously, there are personality challenges. You know, we don't get along with everybody all the time.

Sometimes we just have different working styles. We view the world through our own lenses, and sometimes the way we like to work or the instructions we give, with instructions we receive, don't land. Whether it's a performance issue or a behavioral issue, I knew a company. It's a huge company. There's an irony in this company because they thought that they taught these skills to other people,

but they were so incapable of teaching these skills to their own employees that the whole corporate culture of tens of thousands of people was passive aggressive. Because nobody ever got hard feedback. 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 passive-rogressive because you've done something totally unrelated that's hurt my feelings or pissed me off. And so you say the thing and we both know that I would react. And instead of reacting, I kind of don't do anything. I'm doing an invisible thing.

Right. And then it would be crazy for you to be like, excuse me, Alex, normally would laughed at my joke. You can't do that. So I tiptoe around going, I know something's wrong. Yeah. I can't be like, what's wrong? Yeah. Because you're like, nothing's wrong. What are you talking about? What are you talking about? Yeah. Well, I made a joke and you didn't laugh at it. Well, maybe your joke wasn't funny. Yeah. This may be a personality flaw. It may be an asset. I don't know. 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 my part of the office, didn't hang it up high on the wall, I 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? And she sends her assistant back to me. He comes over and says, Jane would like you to take your picture down. And I would say, tell Jane no. You know, they go back, and I'm giggling and, like, having a blast. Because just come up to be like, hey, Simon, we got an aesthetic here.

You know, I know you want to make a little space for yourself. Let's compromise and come up with the 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.

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

I was like, look at you. Look what you are now. Well, I have more skills. I'm not sure I have the maturity. So I'll be like, you know, baby steps, baby steps. It was 20 years ago. Okay, I'm curious, other than passive aggression, what did other things you notice for yourself? that get in the way of having hard conversations.

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

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

So I think that's part of it. You know, we don't want to hurt somebody's feelings. Yeah. For me, one of the things that stops me from having hard conversations is believing my own story of them. Like, I think there's like a narrative building component that sometimes happens. Like, oh, you're working with someone. They do something once.

And you're like, huh, weird. A little annoying. They do it a few more times. And you're kind of thinking to yourself, okay, well, it's a little frustrating that they're doing this. And then they do it a little bit more. I kind of think that they are this way. Like they are lazy or they are not that considered or they are not thinking about this.

So the longer you wait, you build up a worse and worse narrative of the other person. Yeah. And you're like accumulating your own proof points, you know. And so then it goes from, oh, this thing happened once or a couple times to this person is this way. I don't trust them. I don't want to work with them. Yeah. And so I think that like arc of narrative building also stops you from having hard conversations

because the more you believe, oh, that this is something fundamentally wrong with that person, then the less faith you have in their capacity to change. Oh, that's an uncomfortable one because I think we've all done that professionally. We've all done it personally where a tension arises and reasonably quickly the snowball builds to the point where you have completely assessed and judged their character. And find all the proof points to prove to prove yourself right. That is so true. As we're talking about this, I thought of two other reasons why I have avoided uncomfortable or difficult conversations. One is when I'm afraid of ruining the relationship where if I address this difficult thing, I fear that they will react in a way by ending the relationship.

or ending the friendship. So I don't want to risk that. I feel like there's like a fear of the cat being out of the bag in that sense. Sometimes I think that there is a truth of our relationship. And if we name that, then something about the relationship wouldn't be able to go on. And so I would rather, like you said, like live in this weekend version of a relationship that doesn't actually feel like

totally right because I'm worried, oh, if I name this thing, then the truth will be out and that'll be it. The other time I've avoided it is I think I've stopped caring. I'm thinking of a real life circumstance right now, actually, where I attempted it and it did not go well. The person couldn't hear me, didn't employ any listening skills.

It was a very hard conversation. In fact, they did everything that we recommend don't. They were hyper-rational. They were very aggressive. They were right. I was wrong. We sort of muscled through it

and came to some sort of like acceptable but imperfect conclusion and then it happened again. And I'm at the point now where I could say something and I'm just like, you know what, maybe it's not worth it. And I'm fully aware

and this is where I'm sitting and the stress right now, which is if I choose not to have the uncomfortable conversation, I'm basically accepting the loss of this relationship. And so do I start the mourning process and just end the relationship, or do I try again? And so I'm going through it right now. 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 care enough to engage on a deep level. And so then you stopped caring.

Well, it was worse than that. I was made to feel wrong. One of the things that makes me think, should I have this conversation or not with this person, is I don't expect for it to resolve. I don't expect for them to suddenly have the skill of listening and making me feel heard. I don't expect to get the thing I need. But should I have the hard conversation just to have the relief? Because what's happening otherwise is I lie in bed every night and play over and over and over the thing I would like to say. And if I have that conversation, will that voice leave me?

me at night. And with no expectation of resolution, I want to stop scheming what I would say and just say it. Or the other thing is just who cares, just move on. Well, I think it depends on what kind of who cares. Depends on, depends on how much I value the relationship. Yeah, there's the like resignation, who cares, let's move on. And then there's the, oh, sometimes I just need to accept move on and not everything's going to be exactly how I want it to be. And I think it really depends. I find it to be a really intense tragedy when I lower the ceiling of what I think of friendship or a relationship or a work collaboration is capable of. I want to 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. Oh, totally relate. I feel morally superior. Totally, totally relate. Yeah. And I know they feel the same way. Yeah. The way that I picture it is like I have this gremlin version of me inside of me. She looks kind of like me, but she's like,

and like every time I like collect something that someone else is doing wrong, I'm like feeding her. I'm like, here, take a cookie. You know, like I'm feeding my own little resentment gremlin. And somehow I feel that like I am superior and the other person is, is wrong for it. I think that that's one. And then I'm choosing not to bring it up. I'm choosing not to bring it up every single time. And like that's how the resentment accumulates.

like these like micro-frictions that I would rather feel justified than be an open communication with someone. It's like so illogical. I still do it all the time, obviously. Even though I know these things. Like 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. But you said it right, which is that resentment gremlin is a self-righteousness.

Yeah. Which is if I can feed the resentment gremlin, then I can feel right. Yeah. And that helps me manage the tension, the discomfort, the anger, and the frustration because at least I'm on the side of right. Totally. You know?

Yeah. By the way, I'm sure the resentment Gremlin feeds on that as well. Because if you have no resentment, he loses a house and he has to go find another body to occupy. Yeah, which is way less fun. Which is way less fun for him. And I think it's also built into our model of hard conversations. The water that we're swimming in of conflict is this adversarial model of like you versus

me. I'm right, you're wrong. I want to prove to you why you're wrong and I want to prove to you why I'm right. I want to win the argument. What does it even mean to win an argument? To be more right or to be more hurt or more the victim party or something?

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

And it doesn't mean I think bad has happened or, you know, your boss is a bad person or anything like that. It just means the conversation needs to happen. Or you feel like you're capable of more. Or you want to redirect your career or you're not enjoying this part of the job and you want to try some other part of the job. And I think these are difficult conversations because we create stress around them because we don't know what the outcome is going to be. We don't want to piss somebody off. We don't want to get it wrong. We create stakes that there may or may not be there.

And I just want to point to the fact that not all difficult conversations are personality conflicts. or disagreements. Some of it is, quite frankly, the normal course of a career. Yeah. And I think that's the most important point is like it's normal. It's going to happen. They have to happen. They have to happen. If you feel like you need a raise or you want to try a different job and you never self-advocate, then you're going to sit there resentful that the company doesn't appreciate your boss doesn't appreciate you. And then you feed the resentment gremlin. You start resenting the person or the company. When you haven't done anything to even make a change.

When you haven't leaned into your ability to have that difficult conversation. Yeah. I think when we realize that hard conversations are inevitable and they're normal and they're just like part of the experience, it changes where we're putting our energy. Because instead of laying there at night, lamenting the fact that the problem is ongoing, while we're simultaneously not doing anything different to try to change it, when we realize, oh, this is just part of the process. It's like a normal thing that's going to have to happen. Then we redirect our energy from trying to avoid, avoid, avoid, avoid hard conversations to like, how do I do it? And then we can actually engage with, okay, there are things that I can do to make this easier. So this is a good segue. Yeah.

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

So you have to have the difficult conversation because it's my annual review and you've got to give me the news. But because we don't have the skills on how to have a difficult conversation, it becomes self-fulfilling. It actually does become a mess because we don't know how to deliver the news. So I think the skill is, just as we said, it's a regular occurrence to advocate for yourself up in the hierarchy. It also is a regular occurrence in performing your job when you're,

you're in mental management or a new leader. So it's just part of the job. And our companies don't teach us. No one teaches us. No one teaches us. Except for now. Okay, Alex, you've been teaching this stuff for years. What is the first step that people can learn in how to have a difficult conversation? 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. Let's say that again. Conflict is a team sport for mutual understanding. Break that down. What I was saying earlier about conflict being something that's inherently adversarial is the you versus me, right, wrong, winner, loser. That crowds out the ability to actually understand each other.

And so if conflict is the mechanism through which the important information that we both need to know to do our jobs, to be in our relationships, to understand each other, that's how this thing is getting surfaced. Okay, well, how do we actually understand this thing? And so to me, conflict is not something that I want to win or lose. I think we can all win if we both leave. and you understand me and I understand you. I understand your context. I understand what's going on for you. I understand what needs to happen now. Inherent in the concept of conflict is it there's another person. So it recognizes that it's me and, which I think is interesting. 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. Right.

You know, like I look at this person. Maybe I love them. If it's a personal relationship, maybe I care about them. Maybe I have loved working with them, whatever it is. And I can't see any of that. Like I see like a monster in front of me. almost. And so when I'm able to relax that and be like, oh, you're not some evil being with bad intentions who's out to get me, but you're just a person who I seek to understand, who I want to help you understand me. It changes everything. So we can both win. 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. Yeah. That's good. Keep going. 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. We find a character flaw. They clearly don't have a capacity for dot, dot, dot, dot. Yeah, and we really believe that. I even just said it to you in recounting my experience. Like they have no capacity for listening. They don't know how to hold space. They're always rational. I literally just did it. And we believe it because we've been accumulating the proof points. And I've completely assessed their entire character based on one tension I'm sitting in. 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. We're both facing the problem together of like what is the situation that we're doing? Like, we are intention. That is the problem. Yeah. There's something that's going on between us that we both don't fully understand that we can try to understand together. Yeah. And it's, it's so beautiful. The image that always comes to me is like a river. And there's this kind of flow through the river. And when we don't bring things up, it's like, we're putting all these rocks in the water can't flow. And we're just like

sitting in that every single day. And so when we can understand each other and we can remove some of the blocks, things can naturally flow. And we're doing that at work. all the time. And we build narratives about each other. You know, teams build narratives about their colleagues. We build narratives about our bosses. We build narratives about our employees. Like, we're constantly building narratives and labeling people based on one or two experiences, finding information. And then the problem is, is we perpetuate those narratives. Oh, the lazy one. Yeah. Oh, the stupid one. Yeah. Oh, the angry one. And we triangulate with other people. I think this is another thing that happens a lot. It's like, triangulating is like, oh, there's

something that's going on between you and me. But when we're in a meeting, you and me and our other coworker, I'm side texting our other coworker like, oh, can you believe Simon's doing this? Oh, classic again. And so then we're building narratives. So we're not just accumulating these resentments and building these stories in ourselves, but we're looking to other people to confirm them

because the more other people I can get on my side, oh yeah, he's the problem. And now what that is is gossip, and gossip is one of the most destructive things inside a company. I know a company, they considered gossip a fireable offense. And they said, if you have attention, you have to learn to lean into it with somebody and don't say anything behind somebody's back

that you wouldn't say to their face. And this is different from venturing. about work and venting, be like, oh, you know, blah, blah, blah was an idiot today. Like, that's fine because it's labeling a behavior that was today. It's not assessing their character. 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 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. whatever it is, right? I need anybody who's in that conversation to interrupt and say, that may be true. They may be lazy. Or they're tired, they're overworked, they're overwhelmed, and simply acknowledging that there are other possibilities that are creating that behavior

makes everybody go, oh yeah. And that technique not only has dramatically improved our culture, but I just think 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. So that's been very, very helpful. Because like once one of those narratives gets planted and mutually agreed upon by everyone, it's so hard to unsalt that. And that person is now playing defense for the rest of their job until they get forced out or quit. Yeah. And everyone loses. Yeah. It sucks for everyone. So it's a lose, lose. Yeah. Okay. So the first element of the difficult conversation is the mindset, which is it's me and you versus the problem. And I recognize that you're not a monster.

This is one thing that has happened. Maybe more too. But the point is. This is not everything about who you are. There's a conflict that exists with us, not necessarily between us, but it's on a table. Okay, so one is mindset. What happens next? 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 listen and engage.

Like, you're really inflamed, you're angry, you're dysregulated. That is not going to be the situation in which you're going to be able to have the most productive conflict. You're not going to be like, huh, conflict is a team sport for mutual understanding. What an excellent opportunity if you need to understand this person who was also a monster. So I think you don't want it to be in the heat of the moment necessarily.

And then on the other end of the spectrum there are people who wait way too long. And so they wait to the heat in 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.

Or they bring it up and create a tension that actually, because it's still festering in their mind. 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. 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. So the point is middle. In the middle, yeah. But just don't do it in the heat of the moment. Don't wait too long. Do it somewhere in between. So for me, I try to wait until it's no longer disregulating my system. So you're no longer angry or rather you won't show up hot.

Yeah, I won't show up hot and it's still alive. It's still relevant. I've had a little bit of distance from it. I think the key is in that period of pause. is to express that I'm taking a period of pause because I care for maintaining something. You need to get yourself to the right place so that you can have this difficult conversation constructively. Because you can have it destructively too. It's not just taking the time that you need, but it's also communicating that you're doing it

because you want to set everyone up for the conditions for it to go as well as possible. So it's like, okay, in this moment, I don't feel like I can listen to you. And I really want to be able to do that. Like sometimes, let's say someone's like, hey, can you talk? And you're doing your thing where you're waiting to calm down, but you don't respond. I don't think that's that cool. That's the passive-aggressive. Yeah.

And so I would say, yes, I want to talk. Right now I feel like I'm too activated to be able to have this conversation in a way that I would want to. Can we do it a couple days? Yeah. So mindset, timing. Mindset timing. Another thing that I like to do is come back to my intention for the conflict. Like I'm looking to feel heard.

I'm looking for resolution. I'm looking for action. I'm looking for it. Yeah, it's like, hey, I know that we both care about this thing. I want to figure out a way to communicate about it so that we can get to this place that we want to both be in. So it's both coming back to my intention and maybe to our shared. And setting a goal, right? So knowing the reason you're going in, otherwise, you're just coming in with the emotion.

Yeah. And there's no destination set for the path you're about to journey on. Exactly. And the thing that I think works really brilliantly about this is that it actually does two things. First of all, it knocks me out of the normal culture of like, I want to win, I want to show why I'm right. Because that's like not actually our highest intention a lot of the time. It's more like our knee-jerk reaction. And so I like to first remind myself of what my actual goal is for this thing.

And that changes the frame. So that's the first thing that it does. And then the second thing is that I not only align with myself, but also start the conversation by naming it out loud, which creates an accountability of like, hey, let's do this thing that's bigger than either one of us is. It like reminds us that we have a shared mission. And then also, if I can feel myself slipping into like, well, you're wrong for this reason and I'm justifying myself and this and that. Then I can remind myself that I'm, I want to. I want to get to the goal. Mindset, timing, setting a goal.

Can I, here's something I do. Yeah, tell me. I make a request for grace. And I've done this before, professionally, personally, I need to have a difficult conversation. So I alert somebody about what's about to happen. Because what I've learned is otherwise you come in hot. And even if you aren't, that's how it's received.

And you get very defensive responses. And so by preparing somebody that this is not going to be fun, there's a beat that they can take a breath. And I ask permission. Because, you know, we talk about timing. Yeah. Like the timing might be great for me. But it might not be great for them.

So I need to have a difficult conversation. Can we have it now? Yeah. 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 alert what is about to happen. So in other words, I'm setting their mindset. And I'm making sure the timing works with them too. Because I also want them to show their best self. Maybe they're tired. Maybe they're disregulated. Maybe they're pissed off. Maybe they're still angry at me.

Simon, I'm still angry at you. I can't do this right now. Okay. You know? So I need to have a difficult conversation with you. Is now a good time. Yes, it is. And this is why I ask for grace.

I say, listen, I know I have to have this conversation with you. I also would rather not. Like, it's so much easier for me not to do this right now. For the good of the relationship, I want to see you thrive here. I want to see you do well and I want to be supportive of you. I have to have this conversation with you. I'm going to get some things wrong. I'm going to say some things badly.

And just to work with me, I'm trying. And by asking for grace up front, what I've learned is the times that I haven't asked for grace, If I do accidentally misframe something, say something unclearly say something wrong, they will latch onto it. And now I'm playing defense. I'm like, well, that's not what I meant. They're like, well, then why are you telling me this? And so it actually goes sideways.

And by asking for grace up front, when I get something wrong 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. And they go, okay. Because they gave me permission at the beginning.

And if they forget, I'd be like, you remember, I said, I'm going to get something's wrong, please. You know? And so I help them get on the right mindset with me. I check in on their timing. I ask for grace because it is complicated and difficult. And I'm not an expert, but I need to do this. And I found that that framing has been immensely helpful. 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 going to try my best. By the way, I'd rather not have this. Yeah. Like, it is so much easier for me not to do this. I can just ignore it. That would be the better option for me. Yeah.

But I'm doing this because I actually really care. And I'm willing to take the short-term discomfort. Over the long-term discomfort. I'd rather have a lot of discomfort now, rather than the slow drip of discomfort for a long period of time. Which is the opposite of what we know. Which is because that's actually more cancerous than what we're going to deal with now. Okay, can I share kind of a crazy one?

Yeah. But it's my favorite one. I think I've told you, but I spent a few months in a Buddhist monastery in France. They have a lot around. Do you speak French? No. No, it was, no, it's mostly in English and in Vietnamese. Okay.

Which I also don't speak. Was there wine? That's all that matters. Absolutely not. What? And it's in Bordeaux. Come on. No wine.

What a waste. It's a monastery. I mean, they're French monks, though. French monks drink. No, they're Vietnamese. And monks don't drink. I mean, what a tease to do it in Bordeaux. I know.

Anyway, they have so much that they talk about, about conflicts and having hard conversations. It's amazing. My favorite trick of all, it has a kind of insane name. But I'm going to tell. because I think it's more likely to stick in your head. But it sounds floofy. But basically, one of their most magic tricks is called watering someone's flowers, which is a very simple but powerful act of telling someone nice things about them.

Sounds so simple. But again, when I'm in the tunnel vision of conflict, it's often impossible for me to think of a good thing about someone. Because there's nothing good. There's nothing good about that. Clearly. I like your hair. Okay, that's actually a great example. So, for example, right after I got back, I was in a conflict with my,

best friend. I have a best friend. She is my soulmate. I think she is the greatest person on the planet. I love truly everything about her. And at the time, this was our biggest fight that we've ever gotten in. And we were in the thick of it. And she was like, Alex, surely you have some tools that we could try to use in this moment. Like, don't you teach this stuff? I said, okay, let's water each other's flowers. And explained what it was, the very simple act of saying nice things back and forth to each other. And she said, okay, let's try it. You start. And I was like, Jesus, guys. I like your hair. And I looked at her truly my favorite person on the planet. And I could not think of a single nice thing to say.

Oh, my goodness. And I was looking at her for an embarrassingly long amount of time. And she knew that I couldn't think of anything. And I was looking at her, looking at her, until I, like, eeked one out. But it was like such a small, nice thing. And it was like more fact-based than anything. Nice pants. Yeah, that kind of thing.

Like, I like this, whatever. There's a great shoes. Totally. But I said it. and then it was her turn. And she also kind of struggled. And she said one that was 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. And you're like, they are good shoes. You're right. I do have good hair. And then I said another one back to her. And it was a little bit bigger, a little bit more meaningful. And I could feel that she was softening a little bit.

And then she said one back to me. We went back and forth. And then it became more substantive. And maybe it took, like, six minutes, and our whole conversation was different. And where we were once kind of like steeled up against each other, like you versus me, you're evil and wrong and I'm right and morally justified. All of a sudden, the armor could soften. So here's what I'm hearing, right? And this is really important. So we've talked about mindset, timing. We've talked about having a

goal, stating that goal, or not, but having a goal, asking for grace. And what I like here is about affirming the other person. Because conflict is hard. And for, some having leaning or 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, 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 frufey stuff. But I do like watering someone's flowers. I think that is actually a beautiful metaphor. Yeah. To lean over someone's windowsill, you know. Just giving them some affirmation that I think

affirms not only that you recognize their value, I've made this mistake without doing that, because I'm like, let's deal with the issue. Without doing that, it does make them feel undervalued, especially if there has been tension. Now, this difficult conversation is affirming that I don't value them. And so giving them some affirmation about their talents, their gifts, their contributions to the team and people love working with them is a good level set. Yeah. And then it allows people to hear the things that are harder. Because they recognize that you don't think I'm a dumb ass. And I think you're thinking about it in terms of one of the impacts of it, which is how does the other person feel when you water their flowers?

And for me, what I've also found, maybe even more shocking, is how it changes my perspective. All of a sudden, instead of only seeing this one piece of the puzzle, I'm able to see the whole tapestry of all the other things that are actually going right. And often when we're having a hard conversation, we're only fixated on the ways in which things are going wrong. I want to say one more thing about watering flowers is because there's so many different ways to do it. I really love to start my hard conversations with it,

because I think it just starts us off in a different place. What do I appreciate? What's working well? what do I want to see more of? And just like 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 try something else right now? Or I'll even just spontaneously say a nice thing about someone. Like you don't need two to tango.

So I think oftentimes with hard conversations, people are like, well, what if the person I'm having a hard conversation with isn't like this? And the way that I think about it is like you can lead the conversation in the way that you want it to be led. And so if you want it to be led in a way that validates the other person's humanity and creates a possibility for something other than just the things that are going wrong in the dynamic, then you can say that. Like you can kind of spontaneously be like, okay, well, I also just want to honor that these are the other things that I appreciate about you. Let me throw a wrench in the works here. Throw a wrench. I hate feedback sandwiches.

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

Yeah. Because they say, well, Simon, you know, you're a good listener. I'm like signifying nothing. Yeah. In this moment, we're talking about this. So thanks for the compliment, not interested. Like, that would probably be my response. Yeah.

You know, I find it pandering. And so if you're going to pay me a compliment, it has to be relevant to the conflict. It has to be relevant to the difficult conversation. It has to be real. It has to be real. It's not a tactical thing. It's not a box that you have to check. tactical thing. That's also what 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 want to say. Whereas this is like you're saying something real that wouldn't normally fit into your perspective in this moment. I'll give you an example how it could work with me, right? Simon, one of the things I admire about you is that you talk about grace,

I think you're good at grace, and so because you are good at grace, my ask is, will you make sure to give me grace in this because I know you're good at it? So I'm like, thank you very much. That would be a relevant and good use of watering my flowers because it's relevant to what we're engaged in. And it's authentic.

And it's authentic. And people can feel your truth. Like we think that we're, we think that we can kind of do the theatrics of things and that it'll work. It'll work if you're doing it authentically. And then that's, that's how it will work. If you're like performing it, it won't do anything. And I have one more thing to add to our checklist.

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

it's getting heated and I just want you to know. And so you can interrupt and reset at any point and go back to any of the other things and sometimes even start again. Like that works too. 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 like, wait, can we stop for one second? I feel like we're going in this direction that doesn't feel like it's going to be productive for either one of us. I'll also personally ask for like a take back. I just said this, but actually, I don't mean it. Can I please take it back? And because you ask for grace up front, you're good to go. 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 up. We'd double down. We'd rather not be wrong. Then take it back.

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 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. But it kind of proves your point. Yeah.

So you double down on it. But you both know that that's not what they meant. But that's also about winning and like you versus me and not, hey, I want to understand you and like let's face the problem together. And so breaking the fourth. a thing that I tried 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 mess something up before I'm willing to also admit that I'd mess something up. I'm like that. Yeah. Like, I want my pain to be admitted first. So if I notice that's coming up, I'll say it out loud. 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, even though I also, I'm sorry.

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

Yeah, but like if there's something that I notice is going to block me, I try to name it as soon as possible. Yeah, that's so good. So it doesn't block me. So it doesn't get in my way. I'm like constantly trying to calm myself out. And this is also the danger of what we're teaching here, right? Which is everything we're teaching here, all of the techniques in all of these episodes. And there is an element of performative and practice and intellectual.

and intellectualizing what should be emotional and human experiences, because you're learning. And that's okay. If you never get past that, where it doesn't become innate and natural, and you move past the checklist performative, because you get good at it, right? Nobody thinks about peddling when you get on a bicycle anymore.

And so I think we have to give grace that if you're trying these techniques out for the first time, it will be hyper-intellectualized. It will feel like a checklist. We're even giving it as a checklist. mindset, timing, like we're actually making it a checklist. And that's okay. And if you keep practicing at some point, like riding a bicycle, you'll just get on your bike and ride. So give yourself grace if this is a new thing for you. And if you bumble and fumble it and forget some of

the techniques, it's okay. But the most important thing is you practice. You do it. You do it because you want to be good at having difficult conversations, not because, ugh, this is part of my job. I'm now a middle management. I have to have this. Damn this. Like you're not doing it because it's some sort of like job requirement. Yeah. But rather you really want to learn this technique because it makes you the leader you want to be and it's good for you and it's good for the people

on the receiving end. I agree. And I think if people can feel that you're trying your best, even if you don't get it right, if you're not perfect at it, they can still feel you doing it. And so I think that's the most important thing to remember. It's like all of these techniques

are just scaffolding to help you connect and understand and build that trust. And I think that's the perfect way to summarize and conclude what we're talking about. which is, though we're making the 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,

this process is messy, no two will ever go the same, just because you nailed it in one doesn't mean it's going to go well in the next time because there's another person involved. And the way you describe these things more as scaffolding, they're there to help prop up what you're attempting to do, but it has to stand on its own two legs. Like these are here to support you because that's what scaffolding is. I would say I'm consistently humbled by how hard conversations are, which is such an obvious

thing to say. But I've been so many years of my life studying these things. And you still screw it up. 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. more heart and more compassion and more ability to understand. Like, they're muscles that I built. And so I offer myself not only grace in the heat of the moment, but also just like over the long-term horizon of, this is so hard. Yeah.

And it can be a little bit easier. And so where we're concluding is you study this and teach this, and you're still learning. Oh my God. I have such a long way to go. It's crazy. Alex, we've had a very difficult conversation about difficult conversation. This has been really, really good.

I think it's been fun. It was really good. A Bit of Optimism is a production of the Optimism Company, lovingly produced by our team Lindsay Garbenius, Phoebe Bradford, and Devin Johnson. Subscribe wherever you enjoy listening to podcasts, and if you want even more cool stuff, visit simic.com. Thanks for listening. Take care of yourself.

Take care of each other.