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Simon Sinek
Today what I want to talk about is people pleasing. Just before we get going, I just want you to know that I want this to be the best experience for you and I will do anything I can so that you're happy.
Alex Simon
Are you people pleasing Reed?
Simon Sinek
Yes.
Alex Simon
It works. I'm so pleased.
Simon Sinek
Think about the last time someone asked you to do something at work and you said yes. When you said yes, did you mean it? Was it like a real full bodied hell yes or was it more like a yeah, yeah, totally. Did you say yes with confidence? Or was there a tiny voice inside you screaming what are you doing? You don't have time for this. Followed by total remorse or self loathing as you slowly recognize that the future you now has more work than you can handle. If any of this sounds even vaguely familiar, then congratulations. You have people pleasing tendencies. And even if you're not a full card carrying people pleaser, we've all done this to ourselves out of a desire to be a good team player or out of fear of saying no. Here's the whoever was asking us would actually have been fine with a no if only we knew how to give it. Instead of taking a summer hiatus, we're presenting a special five episode series of a bit of optimism to go deep on human skills. The things that help us connect, collaborate and succeed in any human relationship. That's why I invited Alex Simon to join me. She's an adjunct professor at Yale and founder of LifeShop where she teaches emotional intelligence. And over these five episodes we will tackle some of the messier human interactions. Like having hard conversations, taking accountability, listening and giving feedback. And in this one, People Pleasing. While so many people are focused on what skills to learn in the age of AI, the people that will succeed are the ones that are doubling down on their human skills. Because even in a world of computers, we still work with people. And being a good colleague or friend means learning how to manage expectations properly, theirs and ours. We will cover three big themes in this episode. First, we debunk the myth that always saying yes is how you get ahead, that it's how you earn trust or get promoted and become indispensable. In fact, saying yes can actually hurt those things. We talk about what actually works. Then we'll explore a six word phrase that can get you out of almost any over commitment. You can use it today. No therapy, no personality overhaul required. A guilt free solution for people pleasers everywhere. And finally, we offer ways to spot people pleasing behavior before those good intentions turn to burnout. That high performer who can Never say no. They're closer to the edge than most people realize. And before you get too good at saying no, please listen to this episode and if you enjoy this episode, also please remember to subscribe. This is a bit of optimism. So people pleasing affects a lot of people more than I think people realize. And it is the desire to sometimes avoid conflict, sometimes to ensure that somebody else is getting what they want. Feels good, you know, going out of your way to make sure that everybody's okay. But the reason it can be dangerous and destructive and the reason I wanted to talk about it today, because in theory it sounds like a nice idea, but it can very often be very self destructive to the people pleaser. Yeah, it amplifies all kinds of insecurities. It also sometimes makes them do things they don't want to do, break their own boundaries, all kinds of things. And, and very often it doesn't actually please the people they're trying to please. So it's sort of like in the long term. So it's kind of like a zero, zero.
Alex Simon
I think the tricky thing about people pleasing is that it's kind of like an extreme version of things that are good and adaptive. Like it's normal to want to be generous and to say yes to things and to want to be liked. And I think that where it tips over into people pleasing is when it becomes almost like an existential need of like, oh, I feel like I'm going to combust if I don't say yes to this thing or tell them I can meet this deadline even though I know I can't, or am like over apologizing even though I know it's not my fault or yeah, like taking on too much work. There's so many different ways that it exhibits itself. And I think that we think of it as like a personal characteristic. And every single time I teach people pleasing, I'm shocked by how many teach
Simon Sinek
people how to, how to stop. People, please, let me teach you how to be a better people pleaser. More yeses, more apologies. I could teach that one. Yeah.
Alex Simon
So yeah, when I, when I teach stopping to people please. I'm shocked by how many examples most people, many, many people have examples that have to do with work. And it's because it's an area of our life in which we're constantly being asked for things. You have to say yes and we have to say no all the time.
Simon Sinek
Can you be a be, can you be a people pleaser at work but not in your life?
Alex Simon
Yes.
Simon Sinek
Or do you think like it's like you're a people pleaser and it just exaggerates at work.
Alex Simon
I mean, I think that there's overlap, but I know people who are really people pleasing at work, but not in their personal lives. And I also know the reverse. We are really people pleasing in life, but at work you're like, oh, no, no, I can maintain my boundaries and I can see say, yes, I can do this. No, I can't do that. It's, it's really interesting to me how it shows up in different areas of our, of our life. I also don't think it's like a binary. I don't think it's like, oh, I am, or I'm not a people pleaser. I think it's more like to me, people pleasing is about how can I say yes when I mean yes and how can I say no when I mean no? And so it's, it's a subtlety and it's a gray area and it's happening all the time.
Simon Sinek
Yeah, I think, I think it's, I think what we're talking about is the dial, which is important. I think all of us are people pleasers at some point, even when it's a lightly, slightly unhealthy. And for people who are people pleasers who are hearing this, even that word, they're like, oh, that's me. And it always comes in that sort of way. It's like nobody's ever like, I'm a people pleaser. People like, you know, it's, it's, it's what I think so interesting about it is there's a lot of self awareness for people who are. And it is, I don't know if it's in the most extreme. I think it is shame, but, but I think people are kind of like either resigned to it or don't know how to get out of it, but it's always, I'm a, that's me. The reason I think it's important to talk about it, obviously, because I want to help some of those people overcome the extreme people pleasing. But even for people who wouldn't classify themselves as people pleasers, I think it's really important to understand it. If you, if you, because if you work with somebody who's a people pleaser, you're sometimes accidentally pouring gasoline on their little fire and not making them feel good at work. And so it's an important thing to talk about even if you're not a
Alex Simon
people pleaser because probably you work with one. And it really.
Simon Sinek
Probably work with one.
Alex Simon
Exactly. And it really impacts the whole team. Like, I remember I used to work with someone who I was really close with personally, and she was. Had a kind of chronic people pleasing situation. And it took me a while to figure it out because we would all agree, okay, we're do this, we're going to do it by Thursday, we're going to do this and that. And then she just wouldn't do it.
Simon Sinek
And she was in the room agreeing to the deadline and then didn't meet the deadline.
Alex Simon
And I'd be like, hey, where is it? You know, what's going on? And then nothing. And I wouldn't have thought of that as people pleasing because there's so many other things. It's like, oh, it's incompetent, it's lack of communication, it's this and that. Like there's so many other things. But really she was just saying yes to something that was beyond her capacity
Simon Sinek
because she didn't want to disappoint. And it's not because she was lying, hiding and faking. Let's make it. Because there's a lot of people who say yes to things because they're lying, hiding and faking. They don't want. It's a bit of an imposter syndrome. They don't want. This is not what we're talking about. This is saying yes because you don't want to go against the grain.
Alex Simon
Yeah.
Simon Sinek
Because you, you find going with the flow and everybody else has agreed to it. I don't want to, I don't want to disrupt it. Even if I have information that everybody needs to know. I don't want to be the one to be. I don't want to be the negative Nelly here.
Alex Simon
Yeah. And I also think, I totally agree. And I think in the moment, her experience was like, oh, I can, I can do that.
Simon Sinek
Yeah.
Alex Simon
You know, like it is not lying and betray. It's not lying, hiding, faking. It's not lying, hiding, faking. Because the moment it feels like she
Simon Sinek
can do it, she talks herself into it.
Alex Simon
Yeah. And then the second afterwards there's like the shit. Like, and then there's resentment. There's resentment everywhere. Right. There's. Then she resents herself. Like, why did I do it again? She resents the team or she resents the assignment.
Simon Sinek
And now she's getting in trouble because she missed the deadline and now she's letting the team down. And now all the shame, now it shows up. Right? Totally. I've.
Alex Simon
Of course I've done that.
Simon Sinek
I feel like a failure of Course I've done that. And of course I've been intimidated by the room or the project. And. And like. And I can. I know when I'm people pleasing because my tone of voice is different. Right. So, like, Simon, you game? I'm like, yeah, yeah. As opposed to. Yeah.
Alex Simon
What do you think you're trying, like, what do you think is going on for you?
Simon Sinek
In my brain is like, you sure? Like, in my brain is like, there's like the little, you know, the angel and the devil on my shoulder. And the devil's like, you know, do it. You know, and the angel's like, do you want to do this? You know, you sure? And I'm. I don't want to disappoint the other person that I'm not interested or that I'll offend them. You know, hey, Simon, can you do me a favor? And I want to be like, no, no. And so I'm like, okay, you know, and now I'm at the position where I've had to. It's exactly what's happened where I have to unstick it. I'm like, hey, remember I said I was gonna do that?
Alex Simon
And. Yeah.
Simon Sinek
And. And what? The lesson that I have learned, I'm better than I used to be. But the lesson that I've learned and. And this, I think, is the first lesson of. To combat people pleasing, I think, is people are actually very comfortable with the no upfront. And it's.
Alex Simon
And how do I clean that up?
Simon Sinek
Unfuck that. Right. What I've learned is, like, if you just tell somebody no upfront, they're. That's. They're actually okay with it. I've learned more people are comfortable with a no when they say, can you do this? They're actually asking, can you do this by this deadline? And it's not passive aggressive.
Alex Simon
There's something in our system that believes, like, the world will end if I say no. And I think the calculus there, or if I'm trying to unwind the inner logic that's going on in my head. It's. There's a part of me that's like, well, that'll just be future Alex who has to deal with, you know, like, yeah, present Alex wants the easy thing, but it's kind of like you're hungry and you want to eat junk food.
Simon Sinek
Yeah.
Alex Simon
You know, you just, like, want to. You're like, okay, I want to eat all the. I always want to eat all this shitty food. But then, you know, you're going to feel bad later. You know, it's not going to impact your health.
Simon Sinek
One of my close friends, Kim, her mantra, and I try and remember it. If it's not an. If it's not a heck yes, it's a heck no. You know?
Alex Simon
Yeah.
Simon Sinek
And like, because. Or the other one that I was like, you know, would you do this tomorrow? It's like, hey, in six months, can you do this? Like, yeah, future would love to do that. Sounds like an amazing thing to do. And the question is, would you do it tomorrow? I'm like, no. Well, then if you don't want to do it tomorrow, you don't want to do it in six months.
Alex Simon
I think that's a really useful thing. I think. I personally struggle with the going back to the heck yes, heck no. I kind of struggle with it because more often than not I feel really intense, ambivalent. Some part of me wants to do it, some part of me doesn't. Or all of me wants to do it, but another part of me knows that I can't. And I think when things are more obviously a black and white, yes or no. I find it easy. Yeah.
Simon Sinek
So what you're saying is it's fine in theory, but things are grayer than that in reality.
Alex Simon
Yeah.
Simon Sinek
Including our own.
Alex Simon
Yeah. There are many different parts of me, and those parts want different things. And I think that the heck yes, heck no dichotomy doesn't often map onto my experience. Like. Yeah, it just doesn't. I find that the context is much richer and more dynamic and more complex than I often think it's going to be.
Simon Sinek
So when you teach people, come to your stop. People pleasing class. And I'm very curious, obviously, I'm. You go around the room and you ask people to describe their experiences. I'm very curious what patterns you've noticed. Is there one kind of people pleasing? 4 kinds of people pleasing? You know, infinite numbers of people pleasing. Like what. What do you. What do you hear? What do you hear in the classroom?
Alex Simon
There's so many. It's a really good question. There's so many different types. I think one big one is like a conflict avoidant. People pleasing, which is like any tension, any rocking of the boat feels like it's the world is ending. And so I'm gonna just do anything to avoid a hard conversation. Another one is like a kind of addiction to approval. I think that's a big one.
Simon Sinek
Interesting.
Alex Simon
And I think this is a really interesting one that plays out at work because sometimes if we like, there's this like a parental boss dynamic where, like Our boss can almost become, like, our parental figures, and our worth feels conditional on them saying, like, you did a
Simon Sinek
good job, and you'll do anything to get that.
Alex Simon
You'll do anything to get that. And there's a part of me that really believes that a lot of what's going on at work is, like, I want to know what I have to do. I want to do it. And then I want to be patted on the head and told that I did a really good job. And, like, if I can do those things, like, if I had enough clarity on what needs to be done, if I can feel useful in doing it, I'm contributing to something that's beyond myself, and I just get the satisfaction, the very simple satisfaction of being useful. And then I can be recognized and someone can give me praise for what I've done, like, that. Those three things scratch a lot of our, like, core human needs.
Simon Sinek
There's a very important nuance here, which is. You said addicted to the approval.
Alex Simon
Yeah.
Simon Sinek
I think everybody wants to know they did a good job, and everybody wants their. Their bosses to say. To recognize them.
Alex Simon
Yeah.
Simon Sinek
And it's. It's healthy to want it.
Alex Simon
Yeah.
Simon Sinek
It drives a lot of us to do good, you know, for those we serve and, you know, want to make them proud, especially if it's a good boss. We really want to make. Make our leader proud. You know, they've invested in us. We want to show them the investment was worth it. But you didn't. That's not what we're talking about here. We're talking about the addiction to the need, which is. It's not. And it stops being about the work.
Alex Simon
Yeah.
Simon Sinek
And it starts being about the approval. And that's an important nuance.
Alex Simon
I totally agree. And I think it's about what is the. What is the price that I'm willing to pay to get that? And so, for me, the way that I think about it is if I'm willing to kind of, like, do my work and do the things that need to be done and I'm setting clear boundaries and I'm, you know, kind of, like, doing my thing, and then I'm getting approval, great. That's like a healthy, beautiful system. Whereas when it slips into more kind of extreme behaviors where I'm sacrificing, where I'm betraying myself in order to get that approval. Can you.
Simon Sinek
Can you. So give us an. Give me an example of that.
Alex Simon
So many different things, like, you're saying yes to things that are beyond your capacity without even checking in with yourself. If you can do it, you're sacrificing like your own life and your own well being. Not just on, like I'm working one late night or I'm working one, two crazy weeks. It's like on a longer term basis.
Simon Sinek
And you're consistently not doing regularly, not coming home in order to make do good. Do right by your boss, not even do right by your boss. Do whatever it needs to do to get your boss's approval. You're sacrificing weekends, nights, family. Again, as you said, not occasionally, but habitually.
Alex Simon
Yeah. And over time, my experience has been that that's led to me feeling a lot of resentment and then the accumulation of that. That's how you end up in burnout. It's like saying yes hundreds of times to things that you don't actually want to do and then staying up late and taking on other people's work and managing other people's emotions. And I think a lot of people think of Burn burnout as like, oh, I'm just like exhausted over time. When actually I think the difference between giving a lot of energy to your work versus burnout is burnout involves self betrayal. And so that's, I think where the people pleasing comes in is you're betraying yourself over and over and over again. And that is what actually compounds and leads to burnout. It's not just exhaustion.
Simon Sinek
I think we've talked about this before, but we had somebody on our team who burnt out and her workload was not enough to burn somebody out. And we couldn't understand it. And I think we talked about it in a different capacity where she was an empathetic ear to a lot of people who were coming to her with all their problems, not just work problems and her desire to please them and always be available to them. It got to the point where she, I mean, the whole thing collapsed. You know, she was exhausted, done. I mean, she quit. She quit her job. Completely burnt out.
Alex Simon
Yeah. To me that like, that screams like invisible self betrayals. Like where you know in your system that you're betraying yourself over and over
Simon Sinek
because you don't want to let them down.
Alex Simon
Yeah.
Simon Sinek
Oh, they're in pain, they're angry, they're sad. You know, they need somebody to talk to. Yeah, I don't want to upset them.
Alex Simon
The image that I always think about is, you know the game Jenga, where you stack the bricks. Yeah. Like, it's like if you're, if your sense of self is this Jenga and each time you betray yourself, you're like taking out one brick, you're taking out another brick. Each time you say yes to something, each time you over apologize, each time you rescue someone else because they can't do the thing that they need to do, it's like brick, brick, brick, brick, brick. And then all of a sudden your whole life is unstable.
Simon Sinek
I think it's such a great analogy because we all do things that are slight betrayals. But it's okay. It's healthy doing it occasionally. The Jenga stack is stable even if you remove some bricks. What we're talking about, the chronic people pleaser that that brick removal continues and continues and continues. And it's healthy to take one piece at a time. But eventually if it's habitual, it has consequences and it's going to collapse.
Alex Simon
What about you? How do you feel like you've seen people pleasing show up at work?
Simon Sinek
So I think I know of one example where somebody is a high performer and they're highly competent, very good at what they do and they, they've con. I don't know where it comes from, but they have to communicate hyper competence at all times to everyone.
Alex Simon
Yeah.
Simon Sinek
And so what they end up doing for fear of saying I don't know or fear of saying I'm stretched too thin or fear of saying this is I don't even know where to begin, they end up saying yes to everyone because they're maintaining. It's not just maintaining their view of themselves of hyper competence, but it's maintaining the image they've projected to everyone else of hyper competence. And that's the pleasing part, which is, don't worry, I can take care of it. That's why you rely on me, because I'm hyper competent. And the problem is they are. The problem is they actually are. The incompetent ones that are people pleasers are easy. Those are easy to spot and we can rush in and help them and coach them. But I think the hyper competent ones, and I know as a, for somebody who's had a hyper competent people pleaser on my team, what ends up happening from the leadership standpoint is we make it worse by accident because they start to gain the reputation of being hyper competent. So we start relying on them more. And I know and I'm pretty good about sort of like people in balance and I ask questions expecting an honest answer. So I'll be like, hey, I got another thing for you. Do you have space on your plate? I do. Are you sure? I just want to make sure. Yeah, yeah, yeah. No, it's good. Like, and can you do this? I don't know if we've ever tried this before, but do you? Oh no, no, no. I got this. So I am checking in and they're lying to me.
Alex Simon
Lying. Lying is a strong word.
Simon Sinek
But yeah, lying is a strong word. They're deceiving me and, or themselves.
Alex Simon
Yeah.
Simon Sinek
The point is even a well intentioned leader who really wants to check in with somebody, make sure they have the bandwidth or the capacity, I can't help. And so one of the things I want to explore in our conversation is not only how does the people pleaser advocate in a way that doesn't disappoint or let anybody down, but helps them protect themselves? And how does a leader or a colleague who works with a people pleaser, how are we able to recognize the signals so that even if well intentioned and asking questions that we, we can actually find out what's going on so that we can intervene even if they say yes. So if they say yes, I can do it. And I go, you know what, don't worry about it, I got this.
Alex Simon
You know, it's so hard because, because the nature of it is very confusing to the people around you because it feels authentically like, oh, they can take it on. Even though a small part of your intuition is like, wait, I really don't think you can. And that's why you're checking, right? Like you're checking.
Simon Sinek
It's hard too. Right?
Alex Simon
It's hard.
Simon Sinek
What if you just doubt somebody who is competent?
Alex Simon
Yeah.
Simon Sinek
And so it's, I mean this, you and I have, this has been our mantra since we started this, which is people are messy, this stuff is messy, work is messy. This is all messy. None of this is crystal and clear. It's hard.
Alex Simon
Yeah. I think to your question of what was your first question?
Simon Sinek
I just want to, number one was I want to how do we offer practical things to the people who are, who are the people pleasers, but also how do we offer practical things to people who work with people pleasers?
Alex Simon
I think it's such a good point and I think often to your point, we're thinking about it in terms of the people pleaser of like what's going on in my system when I'm saying yes, it's something that I'm not a yes to. And I think the way trying to understand what are the different impacts that it has on the whole team or on the whole or on our relationships is a totally other side of it that I find to be really important because it goes Against a lot of the things that the people pleaser internalizes. For me, one of the greatest myths about people pleasing is that somehow it'll work. You know, like, you really think it's gonna work. And that's because in the short term you get this, like, hit of a good feeling, you know, like you say yes to someone and someone's like, thank you. Thank you so much.
Simon Sinek
Oh, thank God you're on the team.
Alex Simon
Yeah, yeah. Like, oh, you are so confident.
Simon Sinek
At least somebody is. Yeah, yeah.
Alex Simon
And like, oh, that's so. And so, like, she's really like this, you know, and, and so that. Or in. Let's say you're.
Simon Sinek
And that's the addiction part, right?
Alex Simon
That's the addiction. Yeah. Let's say you're fearing the conflict. That's, that's the type that you are, like, in the moment, you do get to avoid the tense situation. It's like, oh, thank God it worked, you know, and then you're not thinking about the long term impact. Like, you're not thinking about the way that it's confusing other people, by the
Simon Sinek
way, like any addict. Like, like, you know, so it's, it's, it's very consistent.
Alex Simon
And what's so interesting is that you, you face those consequences every single time. You know, my sister always asks this question, what's the mistake that you keep on making? Which I think is such an amazing question because, like, we all have the mistakes that we keep on making. Even though we have to face the music after 10 minutes, after 10 days, after whatever it is, like, we still sometimes, like, have to make the same mistakes over and over and over again. And so I think something that I have found a lot of solace in is reminding myself that I'm going, like, future Alex is going to have to deal with this and that it's also not just me. And that kind of makes me think about the other element, the other myth of people pleasing, which is that you're somehow doing it for other people. Like, oh, if I'm saying yes to something that you're asking me for, then I am a good person. I'm a good, generous, selfless person who's like, sacrificing. And there's like a kind of moral righteousness to that. And we also associate. Like, if I'm saying no, that makes me bad. Like, I'm not doing something that you want me to do. That's bad and that's selfish and ungenerous. And I think the internalized idea that when I'm saying yes to other people, it's about making their lives better. I actually want to kind of turn on its head if the way that I think about it is that it's actually paying a price of the truth so that you can soften your own discomfort. It's.
Simon Sinek
I mean, let's be very blunt and let's be harsh. And I say this with love.
Alex Simon
Okay. What are you gonna say?
Simon Sinek
Not to you. Okay, but people pleasing, not making people please and not saying yes, but we talked about it as Jenga, but the. The uncontrollable urge to keep pulling bricks out of the Jenga pile. Right. We're distinguishing between healthy, pleasing, and unhealthy. And I think you're saying this. I'm just going to be blunt about it. It's a selfish act, which is you're not doing it actually to serve the other person. You're doing it to either avoid the conflict or you're doing it to feel the little dopamine hit of well done. It's actually not even dopamine. It's serotonin. Probably both, actually. But it's the desire for the approval that you become addicted to. And it's. It is like any addiction, it is actually quite selfish. And this is what you're saying, I think, which is to turn it on its head and recognize that by saying yes constantly, though, you're pleasing yourself in those moments. Yes, you hurt yourself over the course of time, but you're actually hurting and disappointing the other person as well that you're trying to please. Because now you have to unstick something or, you know, try. And you. You use. The example you gave is from your own experience with somebody who said yes to something, missed the deadline, and then shut down, and couldn't even respond to emails. When people like, hey, by the way, those are like, hey, I can help you. Like, you know, if you haven't made the deadline, that's okay. We've got a whole team here, like, what's going on? But their ability to be like, I shouldn't have said yes, or I screwed up the shut. Now there are ripples. There's now discontent. There's now the ripples of, like, when you miss your deadline, it affects other people's deadlines. Like, we're waiting on your work to do this work, you know, And I. And it's. It's all because of. And again, I'm being. I'm exaggerating the point to make the point, but all because of the selfishness of the desire to get that. That approval and make somebody else happy. In that moment, it actually becomes not the selfless act you think it is.
Alex Simon
I think I resonate with what you're trying to say. I think for me, labeling it as selfish to me activates like the shame part of my mind, which for me shuts down my capacity to like, engage with it in a self extreme. Yes. To me it's. I'm trying to do something well intentioned. Well intentioned. And the impact of it isn't what I think it is. And it's not. I'm not trying to act out of self interest. It's probably some protective thing from my childhood.
Simon Sinek
Yeah.
Alex Simon
Probably some time in my childhood I had to internalize that I couldn't both be myself and. And be safe and accepted by someone else. And so I picked being safe and accepted by someone else. Over. There we go over staying true to what I know.
Simon Sinek
That's a much better way of putting it. Thank you. You're right.
Alex Simon
And I think maybe if my instinct is, oh, I think I'm doing this for the other person, I find it helpful to turn that on its head and say, okay, if I think I'm doing this for the other person or for my team or for my boss or for whatever it is for my company, actually trying to show myself that it's not saying yes, that will be the best saying yes when I can't do something. It's not that that will be what's best for my team or for my boss or whoever it is, but actually saying the hard, harder but truthful thing in this moment is in the long term. That's how I'm integrity to my team and to my boss in doing all these things.
Simon Sinek
You know, maybe I am a people pleaser. I realize, you know, I've had to learn to say no because I ended up hurting myself and others because I just, I became. I became unreliable.
Alex Simon
Yeah.
Simon Sinek
You know, don't give that to Simon. He's unreliable. And that didn't feel good. Like I got a feedback like, you're unlucky. You know, we can't rely on you. And I was like, what? And it's because it wasn't because I'm irresponsible. It's because I said yes to too many things and couldn't do it all. And I've had to learn that saying no made me. Made me reliable.
Alex Simon
Yeah.
Simon Sinek
And I confused getting everything done as reliable and rather reliability is not the ability to execute everything. Reliability is accurately managing expectations. And I became more reliable when people like, we need this and I'd be like, I, I, I can't. Or if you, if I can, if I can take something else off my list.
Alex Simon
Yeah. It's like also zooming out and being
Simon Sinek
able to see the big picture and, and now they get to decide with me if they really need me to do it. Then we have to take something off the list.
Alex Simon
Yeah.
Simon Sinek
Or if somebody else can do it or it can maybe happen at another time. And that's, I had to reconfigure what reliable means in my own head. And to be reliable, it means accurately managing expectations.
Alex Simon
Yeah.
Simon Sinek
By the way, saying no to everything is also unreliable.
Alex Simon
Yeah.
Simon Sinek
Because that's also not relying on it, I'm afraid. But that's, that's also not manage expectations because I have to do something.
Alex Simon
Yeah.
Simon Sinek
So very interesting. Yeah. And it was never selfish when I said yes. It was always well intentioned and sometimes an exaggerated sense of, I mean this is an exaggerated sense of what I'm capable of, what I'm capable and of time. And it was not a conscious desire or ignorant. It was never ignorant. It was really well intentioned and sometimes forgetful of what else I've got going on. And I never said let me check. Which by the way is a viable answer. Can you do this? Let me check, let me get back to you. And it was always a desire to, to be a great team player.
Alex Simon
Yeah.
Simon Sinek
So I guess I've never described myself as a people pleaser but I've definitely, I've definitely had elements of that that I've worked very hard to work out because I got negative feedback.
Alex Simon
Yeah. And I think tracking the long term impact of saying yes when you don't mean yes is a good way to check in with yourself. It sounds like that's the journey that you were on is.
Simon Sinek
Yeah.
Alex Simon
You were saying yes to all these things, then you weren't able to follow through, then you felt disappointed or I
Simon Sinek
was putting myself in horrible positions where yeah, I'm just working too hard for fear of, you know, being unreliable.
Alex Simon
Yeah. And I think people who have people pleasing tendency can really recognize that of like the intensity of the experience of being asked for something that you know you can't do. Saying yes to it, then feeling self loathing, then feeling, then not being able to do it, then feeling shame that you're not able to do it, then feeling accountable, but also even then even more intense self loathing and then you're kind of just like in this spiral and then you're fixating on all these emotions that you're having instead of actually just doing the thing, you know, it's a whole, it's really a rabbit hole and it really, I have a lot of compassion for it and I've done it a lot of times.
Simon Sinek
The thing that I think is so interesting about people pleasers, there's some deep seated childhood, like, overbearing dad stuff. You know, like if she let down her dad, you know, she was the worst person in the world. And so I became that, that figure, that parent figure. And so I remember like when we would work together and she would show me stuff and I could, I would ask a question because it, like it didn't add up. Like it didn't make sense. Like literally the math didn't make sense, you know, And I'd ask a question and she would lie to me. I mean, she just flat out lie about what happened. Because for her, telling the lie and being right was actually the better option than just saying I screwed up and fearing that she was letting me down. I would rather that. And I'm like, if you like, I. Because once they sniff the lie, I'm going to keep asking questions because it won't make sense. And that's when it's going to feel stressful for you because I'm going to keep pummeling you with questions because it doesn't make sense. It's because you're lying. And I remember once, like I even remember where we were. We're on a plane on a business trip together and like something didn't make sense, Something wasn't aligning. And I said, what happened here? And she like, sort of like, oh, I, I screwed that up. I went, okay, well what's the right answer? Then she went, I think it's this. I'm like, okay, great. And for her to see, like, nothing happened.
Alex Simon
Yeah.
Simon Sinek
And. And very high performer. Very. It's one of the reasons she was a high performer.
Alex Simon
I think that's beautiful. There's an idea that I'm obsessed with, which is this idea of a positive corrective experience of when you have something that you think is going to go one way. Oh, if I make a mistake, Simon will hate me forever. And then instead of the worst fear being confirmed, you have an opposite experience. It corrects your assumptions about what's going to happen in a positive way. And it like rewires something in your system that's like, oh, I can make a mistake.
Simon Sinek
That's what happened.
Alex Simon
Yeah.
Simon Sinek
It didn't happen immediately, but it didn't happen over the course of time. She had to dip her water. Her toe in the water. And to discover. And, and, and so like when we think about if you work with a people. Please.
Alex Simon
Exactly. Yeah.
Simon Sinek
Right. Which is. And I remember I. Because I couldn't just tell her. Like, telling her isn't enough. Isn't enough. And she made. She wouldn't believe me. You know, I'm like, or maybe she
Alex Simon
would believe you on a rational level, but her. Something in her system would still fear it.
Simon Sinek
Right? And so like, even when we had the conversation more than once, I'm like, you gotta just tell me. And I'm cool with it. Don't. You know? But at some point, I think I said, you have to trust me. Just try it out next time. Like, just tell me what happened, or tell me something went wrong, or you made a mistake or you screwed up, or you didn't know you needed help, like any of those things. And I want you to see how I will respond because I guarantee you it's different than what you're experiencing now because you feel unbelievable pressure now because the work is wrong and you're defending it. And that's why there's a tension between us. You need to try it out. And she did. And the first time it went okay. And the second time it went okay. And the third time it went okay. And over a course of trials, eventually she became very relaxing. Ah, man, I screwed that up.
Alex Simon
It's such a beautiful thing. And to me, you. You executed it with so much love and grace. And that's also like I. When I. You asked a question earlier of what do you do as a leader or as a teammate when you're working with someone who has this tendency. And this is one of the things that I do, is I try to create a positive corrective experience.
Simon Sinek
I want to say that again because it's such a great phrase, a positive corrective experience. I like this idea of a positive corrective experience because corrective by itself sounds punitive. Like, you know, when you have anything corrected, it's just like, oh, please, you know? But a positive corrective experiences, which is, I am correcting something here, I'm correcting behavior, but it's going to be such a positive environment for you that you will find yourself craving it or at least being okay with it.
Alex Simon
I really love it and the way that I try to do it. So, for example, my chief of staff, who I adore and trust completely, I love her so much. She also has this tendency. And so whenever she's not communicating with me about something, I know that something has happened. And I'm trying to create the sense of safety so she knows that she can come to me. And instead of withholding information out of fear, she can be honest. And so the way that I tried to craft this positive corrective experience is first I try to do what you did of tell her. So on a conscious level, she knows, hey, it's going to be okay. I just really want to know. I trust you and it's gonna be okay. But that, like you said, is kind of not enough. And so then I tried to give her some experience that allows her to feel in her system, oh, I have this fear that I'm gonna be abandoned or I'm gonna be rejected or I'm going to let someone down, I'm gonna disappoint them, I'm gonna have this fear. And then instead of confirming the old fear, the old belief, then I give her this other experience. And so that's a lived thing. And then what I try to do is the thing that I would maybe add on is I try to name it. So I try to be like, I bet you thought that this was going to happen. And now can you feel in your system that this other thing happened? And then I try to offer this kind of.
Simon Sinek
Over the long term, two thoughts come to mind. One is if we go back to the real experience you had of the person who was people pleasing and then, then just started ignoring the emails.
Alex Simon
Yeah.
Simon Sinek
The problem is if, if you're the leader or the colleague and you get no response or not the response you need, the emails become terser and angrier.
Alex Simon
Yeah.
Simon Sinek
And now we're reinforcing a negative corrective experience. That's a negative corrective experience. Okay, I screwed up. But look how, look how it's going. So I'm certainly not going to admit anything could go ever wrong again.
Alex Simon
What that does is just amplifies the shame.
Simon Sinek
It just amplifies the shame.
Alex Simon
Being stuck in the shame spiral is not going to help you get out of the behavior.
Simon Sinek
And the other thing that I thought of when you're in the rational part where you're explaining something, and I talk about this a lot because I love it, which is the human brain cannot comprehend the negative. Right.
Alex Simon
What do you mean?
Simon Sinek
I'll prove it to you. You ready? Ready.
Alex Simon
Yeah.
Simon Sinek
Don't think of an elephant. Right. You can't tell the human brain not to do something.
Alex Simon
Yeah.
Simon Sinek
This is why they tell parents, never tell your kids, don't eat on the couch. You say to your kids, eat at the table. You tell them the behavior you want, not the behavior you don't want because all it does is reinforce the thing you don't want. Right. And so when we say things like, no, you have to tell me the truth, you won't get in trouble, all we're saying is you're going to get in trouble. And so what we have to learn to say is no, you have to tell me the truth. I promise you it'll be a nice experience in a safe environment if you tell me. Yeah, right. We have to tell them what they're going to get, not what they're going to avoid. So that's another thing that's really important to use affirmative language when having the rational conversation about consequences of the continued people pleasing.
Alex Simon
I love that. I've never heard that before.
Simon Sinek
It's a good one. Okay, now we've talked about the person leading the people pleaser a little bit. Let's talk about the people pleaser themselves. Can you please share some of the tricks and techniques that you teach to actually help the people pleasers?
Alex Simon
Okay. There's so many that I love. One that I really love you kind of mentioned earlier, which is, Let me get back to you. And so I think for people who are really trying to work on this behavior, having a rule for themselves, a challenge that whenever anyone asks them for anything, they have to say, let me get back to you. Even if they think that they're going
Simon Sinek
to do it no matter what.
Alex Simon
No matter what.
Simon Sinek
Because it's the practice.
Alex Simon
It's a practice and it's building the muscle of.
Simon Sinek
And you learn when to deploy it later. But right now, do it in extreme yes.
Alex Simon
Because the knee jerk answer is always yes, you know, and in the moment it feels like an authentic yes. And so creating that a little bit of that distance of just for 24 hours or for 2 hours or whatever it is. I'm going to actually check in with myself and I'm just going to see can. I'm going to check in with my to do list. I'm going to look at my schedule, I'm going to check in with someone else and what I need to actually get the information that I need. Can I say yes to this? Another one that I'm obsessed with. I call it sharing the dilemma. Maybe you have a different term for it.
Simon Sinek
Sharing the dilemma.
Alex Simon
Go away. Yeah. Because often when someone asks me for something, I feel mixed. Right. Part of me wants to do it, part of me knows I can't. Part of me thinks maybe I can. If I do this Thing. And we often put ourselves in a position of needing to say a yes or a no, when sometimes we can share something other than a yes or no. And that can be true to our experience. So there are many different ways to share the dilemma. One way is to share the context of, okay, I want to do this thing. I'm also thinking about this. These are the other competing priorities I have. And so you can just share the context. That's one. Another thing that you can do is you can share when you don't know, because oftentimes when people are asking us for something and we don't actually know the answer, I don't know if I can go to this event. I don't know if I can take on this piece of work because of this thing. Then we, like, don't answer, and we fear. We either say yes or we don't answer. Instead of saying very simply, like, I don't know if these are the things that I'm waiting for. Let me get back to you. And then the other thing that I like to do is I like to share the full, like, my full internal dilemma. And it sounds kind of crazy, but it really works because it creates a sense of like, oh, we're on the same team trying to figure this thing out together.
Simon Sinek
Let me understand what you mean. So I'll give you a real life example. So go to a colleague and be like, I need you to do this.
Alex Simon
Okay. So if I was trying to share the dilemma, I would say, okay, great, I really want to do this thing, and this is my dilemma. So these are the other things that I'm thinking about. These are the other things that are on my plate. And this is why those other things are important. And so I try to show why they're important to remind my teammate of, oh, our shared mission. We're both trying to work on this big thing. You have this one piece of it, I have another piece of it. So I try to share that I feel a yes to it. I try to share kind of like the big picture, the bird's eye view of, of the competing priorities. And then I also try to acknowledge the other person's position or their needs. So I'll be like, I know this is important to you because you need this and this and this, which also helps them feel like, oh, we're all on one team. We're all in this dilemma together. It's not like a kind of you versus me. I'm going to either say yes and you're going to be happy with Me, or I'm going to say no and you're going to reject me and I'm not going to be worthy or useful. And so I try to share kind of like the big picture view, and it creates the sense of togetherness. And. And also, instead of being the end of a conversation, like you asked me for something, I say yes or I say no. That's the end of the conversation. When you share the dilemma, it's the beginning of a dialogue of, oh, it's not that it ends here. Yes, I'm doing it. No, I'm not. It's okay. Interesting. Well, maybe if I take on this piece of work, then you can do this. Oh, cool. Well, I can do what about these three things? If so. And so can do this other thing. And so we're kind of sitting in the problem together, trying to figure it out together. And that is the beauty of sharing the dilemma. It starts a conversation, it starts a dialogue to find something that works for everyone.
Simon Sinek
There's a nuance here that has to be underscored and it goes back to that affirmative language. So when somebody is sharing the dilemma, as I'm listening to you, that affirmative language really matters. So you don't say. You want to avoid saying, I don't want to say no.
Alex Simon
Right.
Simon Sinek
Because now what the person who asked you just heard. So it's like, okay, you're about to. You're just telling me no.
Alex Simon
Yeah, right.
Simon Sinek
I don't want to say no. But yeah, you know, I got this thing and this thing and this thing that's actually not sharing the dilemma. That's not making the other people, the other person feel affirmed and asking for help. It would. Sharing the dilemma would, as I'm learning from you, I'm sort of gaming it out of my own head. I need you to do this. Ah, yes. That needs to get done. I'm working on this and I've got this. I'm trying to figure out how I can make time to prioritize that. So sharing the dilemma is literally that. It's the thinking out loud of trying to solve the problem they're asking you to solve by moving to moving the pieces of the puzzle around. You're doing it out loud. That is sharing the dilemma. It's. It is not. I want to say yes. You know, I want to make sure this happens, but, you know, like, I don't want to say no. And it's not dumping your stuff on the other person's plate. It's literally them watching you process what you have to Move around in your schedule or your day or your week to ensure that that thing that you think you agree is very important needs to get done. And simply sharing the dilemma. Somebody else can say, oh, I didn't realize you were working on those things as well. Yeah, take that off your list and do this instead. Or, you know what, continue what you're doing. I think it's easier if I do this myself.
Alex Simon
Yeah.
Simon Sinek
And you never actually said yes or no. And this is what I think so valuable about the sharing the dilemma. It's not I want to say yes or I don't want to say no. It's not saying yes or no. That's your very point. It is removing the binary nature of a question. Can you do this? And it is literally going through the steps of trying to get to yes.
Alex Simon
We don't want to say, oh, I really want to help you, but this and this. I really want to help you. And these are the other things that I'm thinking of. So you're not.
Simon Sinek
It's not negating.
Alex Simon
Yeah. You're not like, fake saying, I want to help you. It's like, yeah, I want to help you. And these are the other things that I'm thinking for. You're not saying, however, But. Except I have to think that I
Simon Sinek
think there's a nice trick because I do this as well, which is I. I say to my team, I'm thinking out loud here. It's a different reason. It comes from, you know, people who think out loud.
Alex Simon
The addiction of things.
Simon Sinek
No, no, it is. But people, especially if you're in a position of authority, people take it as a task when it's just a thought. So I've had to learn to say, I'm thinking out loud here. So everybody puts their pens down, right?
Alex Simon
Everything's a muscle.
Simon Sinek
Everything's a muscle. So work the muscle by overdoing it in the short term when sharing the dilemma. I think it's a great device to simply say, let me share the dilemma.
Alex Simon
Or even like, yeah, I'm in a little pickle.
Simon Sinek
These are the things that I think about pickle dilemmas. Like, I think the device saying, yes, here's my dilemma. Yes, I'm in a bit of a pickle. Is a nice way to get somebody to say it the right way and get it out.
Alex Simon
I love that. Yeah.
Simon Sinek
What else?
Alex Simon
Another one that I love. Okay. Have you heard of the term villain era?
Simon Sinek
Villain E R A or E R
Alex Simon
R O R E R A?
Simon Sinek
Villain era. Yeah, like the era.
Alex Simon
It's kind of Like a modern term?
Simon Sinek
No, I don't know the term villain era.
Alex Simon
It's like when you're.
Simon Sinek
Isn't that a. Isn't that an album by Taylor Swift?
Alex Simon
Maybe that's too modern for me.
Simon Sinek
One of her eras.
Alex Simon
So. Have you heard of the term villain era?
Simon Sinek
I have not. Is this modern slang? Is this about to make me feel old?
Alex Simon
It's probably gonna make you feel old. Okay, but maybe to other people listening.
Simon Sinek
Is this on fleek? Wait, that's old.
Alex Simon
I wouldn't go there. Okay, so a villain era is like, it's a modern term. And it's basically when you move from being your overly accommodating, like, nice to everyone, you know, prioritizing everyone else's needs over your own to like, I'm prioritizing myself and I'm not gonna say yes to things that I'm not a yes to.
Simon Sinek
So basically you're handing in your wings and your halo and you're trying out the horns for size.
Alex Simon
Exactly. You get it.
Simon Sinek
And like, I like the wings and the halo, but let me just see what this little pitchfork and horns are like. So it's trying out the other.
Alex Simon
But the reason it's called the villain era is because to everyone else in your life who's used to you being overly accommodating and kind of a pushover and being able to, all of a sudden those things have changed. Like, we change our behaviors, but our relationships need to catch up with us. And so this is another thing that I think about is like, especially if you have like a chronic people pleasing situation, whether it's people in your life or people at work, they're used to interacting with you in a certain way. And so when we decide internally that we want to change that it takes other people time to catch up. And that reaction can feel quite intense. And that change can be quite surprising to people. And so I think the mistake.
Simon Sinek
Are you advocating for villain eras or are you not advocating for villain eras?
Alex Simon
I'm advocating for two things. First of all, when you make a big change, that's going to impact your dynamics with other people, I like to name it, be like, hey, I'm really working on.
Simon Sinek
Do you have to tell people?
Alex Simon
I like to tell people. That way they know what's going on. And also, maybe they'll even be on my team of like.
Simon Sinek
Because otherwise you're going to start acting differently and people are going to be like, what the hell?
Alex Simon
Yeah.
Simon Sinek
And now they label you the villain.
Alex Simon
Exactly, because. So I try to name it. And in a way that like hopefully inspires people to want to be on my team with me. For me, let's say it's my boss or let's say it's a friend of mine or my partner, probably they know they're feeling the long term impact of my people pleasing and so I can maybe tell them like, hey, just want to let you know that I'm working on this. I'm trying not to say yes to things that I don't actually have capacity for, or I'm trying to be more authentic, like, will you support me in this? And will you maybe will you check with me when I say yes to something? Will you check and say, are you sure? You know, are you sure you actually want to go to that thing? So I try to name that I'm changing the behavior and I try to do it in a way that is with warmth rather than harshness. I think when people first start setting boundaries or standing up for themselves, they're so worried that they won't be able to do it, that they're overly firm and they're overly cold and that is really freaky to people. And that also creates negative corrective experiences. And so I think especially when you're starting out or when I'm starting out, I'm setting a new boundary for the first time. Something that I like to do is set it with warmth.
Simon Sinek
Okay, here's what I'm taking from this that I really like. So we've got three things. We've got. Let me get back to you. We've got. I want to share the dilemma or share the dilemma. And what I'm hearing this one, which I really, really like, this plays to all my biases, which is asking for help and letting others be a part of it. Because I think one of the, one of the things that we're setting up people pleasers to fail is that they have to master all of these techniques that we're talking about all by themselves in order to overcome their people pleasing. And part of it is actually that's not true and that's not possible. And I think saying to a colleague or a boss or whoever to just be open and say, I know something about myself that I'm not proud of, but it is what it is, which is I'm a people pleaser and I know that in the short term it feels good for you and for me. And I know over the long term it hurts me and it probably hurts my work product. And so I'm really working to get over it. Here are the Techniques that I'm gonna be practicing. One I'm gonna start saying, let me get back to you. When you ask me to do things. Sometimes It'll only take 10 minutes or an hour, you know, but it's one of the techniques I'm practicing. The other one is I'm going to share the dilemma when you ask me to do things. And if I forget, can you please remind me? So for example, if you come to me and say I need you to do this, and I very quickly go, yes, it's because I forgot. Can you say, do you want to think about this before you get back to me? Or if I say let me get back to you and I come back with the yes, it's like, do you want to share the dilemma with me? So I think getting your colleague, your boss, whoever to be a part of it is very reinforcing of the positive corrective environment. But also it be. It builds trust and collegiality in between the two of you, which is only a good thing. And I really like that. And it makes the other person complicit in your success.
Alex Simon
Yeah, I love the way you put it. It's building trust because I think often the people pleasers experience is this intense loss of trust. Loss of trust with themselves and also the like feeling backed into a corner where they know that they're hurting the trust that someone else has given them, but they kind of don't know what to do about it.
Simon Sinek
People pleasing isn't just my problem. Yeah, we all have our issues, you know, how do we all help each other with our issues, which I love. Me too, because you know my definition of a healthy corporate culture? No, tell me when everybody agrees to grow together. And so a healthy corporate culture is when we agree to grow together before we end. I just thought of one other technique that has really helped me and it's a, it's, it's. I'm going to try and make up a term like your positive corrective environment, which is affirmative deadline adjustment.
Alex Simon
Affirmative deadline adjustment.
Simon Sinek
Yeah. Or ada.
Alex Simon
Nothing like a good tla.
Simon Sinek
Yeah.
Alex Simon
Three letter acronym.
Simon Sinek
Yeah. So Affirmative deadline adjustment. So I'll give you real life scenario. Hey, Simon, can you do this? Yes, I need by Friday. No problem. Okay. And then I'm going nuts trying to get it done by Friday. And then I'm either successful at great personal cost or I'm about to fail. And I call and be like, I can't do this by Friday. And it's probably Friday morning, you know, I can't do this Today. And they're like, that's fine. Anytime next week we'll do. And you realize when you say, when do you need it by people just make shit up.
Alex Simon
Everything in working is made up.
Simon Sinek
It's like, when do you need this by? Friday. Okay. You know, and so what I've learned is if they don't give me a deadline, I know my own schedule. Let me get back to you and say, can I get this to you next Friday? Yeah, that's no problem. Oh, can you do next Thursday? Yes, yes, I can do. Or when they say, when do you need by Friday? Is next Tuesday okay? Yeah, next Tuesday is fine. And I found out that very few deadlines that I was given are actually deadlines of which there are repercussions if that deadline is missed. And most of them just needed to be done by a certain period of time and simply asking, is it okay if I do? Then almost always it went my way. And so that's another little trick which is affirmative deadline adjustment. Yeah.
Alex Simon
And it's also the opposite of what's normally happening, which is like, oh, I'm like the whole world is caving in on me. And I'm.
Simon Sinek
Well, you just assume that whatever you're being told is like the thing. And. And there's also a terrible technique which a lot of leaders have learned and I wish they would do away with it, which is giving people fake deadlines. Well, if I give them a fake deadline, that way it'll get done on time. And if they miss it, well, it's okay, we're taken care of. Because the minute you figure out all the deadlines are fake, then I miss all the deadlines because they're all fake anyway. You know, my publisher learned this the hard way. They used to always give me fake deadlines and I just started ignoring all their deadlines because they were all fake anyway. And I would tell them, tell me the absolute God's honest truth deadline, because then I know there are serious consequences if I miss it and I'm gonna hit the deadline because there are serious consequences. So anyway, different conversation.
Alex Simon
Are there any other tips for people pleasing either for the people pleasers themselves or for people working?
Simon Sinek
I think this is a good list. I think what we have is a good list. I'm going to just review. Let me get back to you. Done in the extreme to start. And then you'll habituate it. Two is let me share the dilemma or share the dilemma, which I think is wonderful. The third one was like asking someone for support. Asking the third One is asking for support and getting help in, in what you're working on. And the fourth one is confirm the deadlines. Yeah, confirm the deadline. Don't just take it for granted that whatever the deadline is, is actually the deadline.
Alex Simon
Yeah.
Simon Sinek
Or the workload or whatever it is. You know, confirm, Confirm. The thing that needs to be done.
Alex Simon
One that I would add, I kind of started it, but I didn't. Just to go back to it, is when we start setting, setting boundaries and saying no when we start, we often do it with this really intense firmness and harshness and coldness. Like we like steel ourselves up because we think that if we're firm, the other person won't push back. And we think if they push back a little bit, I'm going to crumble because I know that I'm new to this. And so we like, we're like overly firm and aggressive sometimes or overly mean because we just think that that's what we need to do, that we think that that's what boundaries are. And I would say you can still be firm while also being warm and while also staying in connection.
Simon Sinek
This is a very, very, very important point. Especially younger generations who are learning about boundaries and boundary setting, they falsely believe that having a boundary is simply saying no to everything.
Alex Simon
Yeah.
Simon Sinek
And there's no quicker way to disingratiate yourself on a team than saying, these are my boundaries. And I'm not. That's, that's not a team player. And every technique that we are going through today is boundary setting because you are now taking some agency into your own workload. The expectations others have of you, the expectations you have of yourself, and you're learning to adjust them in a way that, that helps you work to your natural best and it manages the expectations of the people with whom you work. That is what healthy boundary setting is. Everything we're talking about today is healthy boundary setting in a way that is constructive to the team. Simply saying, I have boundaries. The answer is no. That's you operating like an island, forgetting the fact that there are other people here. And just as it is not a good idea to miss deadlines because there are implications, it's also not a good, not a good idea to simply start arbitrarily saying no to things because there are things happening that you don't know about. So this is a very, very, very important point that we're making here. These are boundary setting things that we're talking about and they're being done in an extremely affirmative and team oriented way.
Alex Simon
Okay. Are there any Other strategies or things.
Simon Sinek
I learned this from the Air Force. In private sector, it's very. This is how. This is a normal scenario. Like, somebody works really, really hard on their PowerPoint presentation. They were two weeks on it, and they have the big meeting, and they do their presentation, and at the end they go, huh, huh? Pretty good, right? Like, that's fairly normal in private sector. In the Air Force, it's totally different. Somebody will work really, really hard on their PowerPoint presentation. They'll come in to the meeting, they'll give the presentation, and at the end, they go, spears. Spears. At the end of their work, they ask for the room to throw spears at the work to make the work better.
Alex Simon
Whoa. I love that.
Simon Sinek
It is fantastic. And so now in our office, it's very normal. It's completely acculturated at our office, where somebody will present their work, and at the end, they'll say, spears. Or somebody will just share an idea and be like, here's an idea. Spear. Or somebody will say, I got a spear for you. And we now have this very relaxed feedback loop where we don't sort of give excessive amounts of praise unnecessarily just to make somebody feel good. Everybody actually wants the spears. And the reason is we recognize we're all working in this together. Everybody wants everybody's work to be the best it can be. And we're all in this together. It's always done with love. Right. The spears, and they're always warmly received. What I've learned from one of the people pleasers on my team, that this culture of spears has allowed them to experience getting negative feedback and not feel bad.
Alex Simon
Yeah.
Simon Sinek
And the stakes are low. Right.
Alex Simon
It's like exposure therapy.
Simon Sinek
It's exposure therapy. And especially because we're all really good about. Instead of just saying, that's dumb, we go, I got a spear for you. They're like, okay, bring it on. So it's. It sets the. And everybody sees the meeting. Like, everybody's like, yeah, good spear. Good spear. You know? And so all this negative feedback that's being thrown at the work, people are seeing. We're not attacking you.
Alex Simon
Yeah. It's, like, oriented towards growth.
Simon Sinek
We're helping the work.
Alex Simon
Yeah.
Simon Sinek
It's always at the work. It's never at you. Because I think people pleasers very often confused that the criticism of the work is criticism of me.
Alex Simon
Yeah.
Simon Sinek
It's not.
Alex Simon
Yeah.
Simon Sinek
It's of the work. And spears clarifies that.
Alex Simon
I love that.
Simon Sinek
Yeah, it's great.
Alex Simon
Yes.
Simon Sinek
There's five techniques.
Alex Simon
Okay.
Simon Sinek
One first one is let me get back to you. Let me get back to you. Work the muscle. Work it a lot at the beginning. Number two, share the dilemma. Number three, Ask for help.
Alex Simon
Yeah.
Simon Sinek
Tell someone that you tell someone your behaviors are going to change and to support you. And even sometimes prompt you with scene number one and two.
Alex Simon
Yes.
Simon Sinek
Number four.
Alex Simon
Affirmative. Deadline adjacent. A really well named terrible, isn't it, behavior.
Simon Sinek
It's terrible. Let's just call it like check the deadline. Number four, check the deadline. And number five, Spears. Ask for Spears.
Alex Simon
Proactively ask for Spears.
Simon Sinek
Or if you're in a position of influence or authority, introduce Spears into the company. Because you not only will help with feedback, but you're helping all your people pleasers on the team too.
Alex Simon
Oh, I love it.
Simon Sinek
But more importantly than us feeling pleased, I really hope that everybody's listening is feeling pleased. Until next time.
Alex Simon
Until next time. Thank you, Simon.
Simon Sinek
Thank you, Alex. A Bit of Optimism is a production of the Optimism Company, lovingly produced by our team, Lindsey Garbinius, Phoebe Bradford and Devin Johnson. Subscribe wherever you enjoy listening to podcasts. And if you want even more cool stuff, visit SimonCinek.com thanks for listening. Take care of yourself. Take care of each other.
A Bit of Optimism: Feelings at Work | PART 1
Host: Simon Sinek
Guest: Alex Simon (Adjunct Professor at Yale, Founder of LifeShop)
Release Date: July 14, 2026
In this special installment of Simon Sinek’s A Bit of Optimism, the focus is on “people pleasing”—that all-too-common workplace behavior of saying yes, even when we don’t mean it. Simon is joined by Alex Simon, an expert in emotional intelligence, to explore why people pleasing happens, how it hurts both individuals and teams, and practical, actionable techniques to move toward healthier and more honest communication at work. Together, they tackle myths, share stories, and outline frameworks for setting healthy boundaries and supporting both people pleasers and those who work with them.
[00:00–03:47]
“It is the desire to sometimes avoid conflict, sometimes to ensure that somebody else is getting what they want. ... But... it can very often be very self destructive to the people pleaser.”
—Simon Sinek [02:30]
[03:47–17:34]
“Burnout involves self-betrayal... saying yes hundreds of times to things that you don’t actually want to do... that is what actually compunds and leads to burnout.”
—Alex Simon [15:17]
[09:41–11:31]
“If you just tell somebody no upfront... they’re actually okay with it. ... Reliability is accurately managing expectations.”
—Simon Sinek [09:41, 27:43]
[12:13–15:12]
“It’s not just about the work. ... It starts being about the approval, and that’s an important nuance.”
—Simon Sinek [14:04]
[17:34–20:49]
[21:04–25:23]
“Let’s be very blunt and let’s be harsh... it’s a selfish act. ... You’re doing it to either avoid the conflict or ... the approval... it actually becomes not the selfless act you think it is.”
—Simon Sinek [23:27]
[36:25–43:26]
Alex and Simon outline tangible phrases and habits to foster healthier boundaries:
“Let me get back to you.”
“Share the dilemma.”
Ask for help and accountability.
Affirmative Deadline Adjustment (“Check the Deadline”).
Ask for Spears – Feedback Culture.
Simon Sinek on Reliability:
“Reliability is not the ability to execute everything. Reliability is accurately managing expectations.” [27:43]
Alex Simon on Burnout:
“The difference between giving a lot of energy to your work versus burnout is burnout involves self-betrayal.” [15:12]
Simon on Leadership:
“Even a well-intentioned leader who really wants to check in with somebody... I can’t help.” [19:33]
Alex on Changing Patterns:
“When you make a big change... I like to name it... I try to do it in a way that is with warmth rather than harshness.” [45:21]
Simon on Boundaries:
“These are boundary setting things that we're talking about and they're being done in an extremely affirmative and team oriented way.” [54:16]
Simon and Alex emphasize that growing out of people pleasing is a journey best taken together—when teams and individuals agree to be honest, supportive, and growth-oriented, everyone wins. By challenging myths and sharing practical tools, this episode offers rich, optimistic strategies for a healthier workplace—one where saying no can be as collaborative as saying yes.
“A healthy corporate culture is when we agree to grow together.”
—Simon Sinek [48:56]
If you enjoyed these insights, don't forget to check out the remaining episodes in this special Human Skills series from A Bit of Optimism.