In short
People-pleasing at work—why saying “yes” to requests you can’t truly do feels good short-term but leads to self-betrayal, resentment, deadline failures, confusion for teammates, and burnout. The episode debunks the myth that always saying yes earns trust/promotions, introduces a practical “get out of overcommitment” approach (a six-word idea referenced as “heck yes/heck no”), and teaches how to spot people-pleasing early.
Guest backgrounds
Alex Simon is an adjunct professor at Yale and founder of LifeShop, where she teaches emotional intelligence.
Key claims
People-pleasing is an extreme version of healthy generosity/liking; it’s about saying yes when you mean yes and no when you mean no. It’s often driven by conflict avoidance and an “addiction to approval.” Burnout is linked to chronic self-betrayal, not just exhaustion. Leaders should create “positive corrective experiences” so people can admit mistakes safely.
Notable examples
A teammate agrees to deadlines but misses them, then shuts down and becomes unreliable. A high-performing person maintains a “hypercompetence” image by saying yes to everything, causing leaders to rely on them more. Techniques taught: “let me get back to you,” “sharing the dilemma,” and naming change (“I’m working on…”) to prevent others from labeling you a “villain.”
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOUnderstanding People-Pleasing
1:14 to 3:48
Discussion on the nature and effects of people-pleasing behaviors.
“the things that help us connect, collaborate, and succeed in any human relationship.”
The Dangers of People-Pleasing
3:48 to 6:18
Exploration of how people-pleasing can lead to burnout and relationship issues.
“version of things that are good and adaptive.”
Identifying People-Pleasing Behavior
6:18 to 7:36
Insights on recognizing people-pleasing tendencies in oneself and others.
“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.”
Navigating Boundaries at Work
7:36 to 10:52
Strategies for maintaining boundaries and saying no effectively.
“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.”
Patterns of People-Pleasing
10:52 to 14:00
Analysis of various types of people-pleasing behaviors with examples.
“And the question is, would you do it tomorrow?”
The Nuance of Approval vs. Sacrifice
14:00 to 17:44
Understanding the balance between seeking approval and self-betrayal.
“which is it stops being about the work and it starts being about the approval.”
The Jenga Analogy of People Pleasing
17:44 to 21:29
Exploring how chronic people pleasing can destabilize one's sense of self.
“And they've, I don't know where it comes from, but they have to communicate hyper competence at all times to everyone.”
Consequences of Saying Yes
21:29 to 27:07
Discussing the long-term impacts of habitual agreement and the need for boundaries.
“For me, one of the greatest myths about people pleasing is that somehow it'll work.”
Rethinking Reliability
27:07 to 28:00
Redefining reliability as managing expectations rather than just completing tasks.
“like you're on, you know, we can't rely on you.”
The Complexities of Saying Yes
28:00 to 29:18
Explore the challenges and emotional toll of always saying yes at work.
“By the way, saying no to everything is also unreliable.”
Show all 24 chapters
The Impact of People-Pleasing
29:18 to 31:06
Understand the emotional spiral and consequences of people-pleasing behavior.
“I mean, she'd just flat out lie about what happened.”
Creating Positive Corrective Experiences
31:06 to 33:19
Learn about the importance of positive corrective experiences for growth.
“And she sort of like, oh, I screwed that up.”
Affirmative Language in Communication
33:19 to 35:36
Discover how to frame conversations positively to avoid reinforcing negative fears.
“I like this idea of a positive corrective experience because corrective by itself sounds punitive.”
Techniques for People Pleasers
35:36 to 36:41
Get practical strategies to help people pleasers manage their responses.
“You can't tell the human brain not to do something.”
Sharing the Dilemma
36:41 to 42:05
Understand how sharing dilemmas fosters collaboration and problem-solving.
“And so creating a little bit of that distance of just for 24 hours or for two hours or whatever it is, I'm going to actually check in with myself and I'm just going to see, I'm going to check in with my to-do list.”
Navigating the Dilemma of Saying Yes
42:05 to 43:28
Explore how to approach requests without falling into a binary yes/no mindset.
“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.”
Understanding the 'Villain Era'
43:29 to 44:26
Learn about the concept of 'villain era' as a shift from people-pleasing to prioritizing oneself.
“Okay, have you heard the term villain era?”
Communicating Change in Behavior
44:27 to 45:56
Discuss the importance of communicating personal changes to maintain healthy relationships.
“and you're trying out the horns for size.”
Techniques for Overcoming People-Pleasing
45:57 to 47:25
Discover practical strategies for people pleasers to manage requests and boundaries better.
“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.”
Affirmative Deadline Adjustment Explained
47:26 to 51:01
Learn about the technique of affirmative deadline adjustment to manage expectations effectively.
“Sometimes it'll only take 10 minutes or an hour, you know, but it's one of the techniques I'm practicing.”
Boundary Setting with Warmth
51:02 to 54:05
Understand how to set boundaries in a warm and constructive way without alienating others.
“And it's also the opposite of what's normally happening, which is like, oh, the whole world is caving in on me.”
Creating a Culture of Constructive Feedback
54:06 to 56:00
Explore how to foster a culture that encourages constructive criticism and growth.
“it's also not a good idea to simply start arbitrarily saying no to things because there are things happening that you don't know about.”
Understanding Feedback Mechanisms
56:00 to 56:55
Learn how to view feedback as constructive rather than personal criticism.
“And especially because we're all really good about, instead of just saying, that's dumb, we go, I got a spear for you.”
Five Techniques for Saying No
56:55 to 57:27
Discover five strategies to help manage your tendency to say yes.
“Tell someone that your behavior is changing.”
Transcript
Automatic transcript. May contain errors.0:00Simon 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. Are you people-pleasing me? Yes. It works. I'm so pleased. 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.
0:38Simon Sinek: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 irony. 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.
1:20Simon Sinek: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.
2:01Simon Sinek: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 overcommitment. 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.
2:44Simon Sinek: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.
3:02Simon Sinek: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 uh break their own boundaries all kinds of things 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.
3:47I 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 I'm 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
4:27Simon Sinek:many teach people how to let me let me teach you how to be a better people pleaser well yeses more apologies i could teach that one yeah so yeah when i when i teach stopping to people please uh i'm shocked by how many examples most people are 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. We have to say yes and we have to say no all the time. Can you be a people pleaser at work, but not in your life? Yes. Or do you think like it's like you're a people pleaser and it just exaggerates at work? 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.
5:04And I also know the reverse. We are really people pleasing in life, but at work you're like, oh no, no, no. I can maintain my boundaries and I can say yes I can do this no I can't do that it's really interesting to me how it shows up in different areas 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 a subtlety and it's a gray area and it's happening all the time
5:31Simon Sinek:yeah 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 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 are like, oh, you know, it's what I think is 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 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 oh, that's me.
6:07Simon Sinek: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. 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 people pleaser. Because probably you work with one. You probably work with one, exactly. And it really impacts the whole team.
6:40Like I remember I used to work with someone who I was really close with personally. And she had a kind of chronic people-facing situation. And it took me a while to figure it out because we would all agree, okay, we're going to 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.
6:58Simon Sinek:So she was in the room agreeing to the deadline. Yeah. And then didn't meet the deadline. 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 incompetence. It's lack of communication. It's this and that. There's so many other things but really she was just saying yes to something that was beyond her capacity. 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 and they don't want, it's a bit of an imposter syndrome and they don't want, this is not what we're talking about.
7:28Simon Sinek:This is saying yes because you don't want to go against the grain because you find going with the flow and everybody else has agreed to it. 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. Yeah, and I also think I totally agree. And I think in the moment, her experience was like, oh, I can do that. Yeah. You know, like it's not lying and betraying. It's not lying, hiding, faking. It's not lying, hiding, faking because in the moment it feels like she can do it. She talks herself into it.
8:03Yeah, and then the second afterwards, there's like the shit. And then there's resentment everywhere, right? Then she resents herself. Like, why did I do it again? She resents the team or she resents the assignment.
8:15Simon 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. Totally. Of course I've done that. I didn't feel like a thought. Of course I've done that. And of course I've been intimidated by the room or the project. and I know when I'm people-pleasing because my tone of voice is different. So like, Simon, you game? I'm like, yeah, yeah. As opposed to, yeah. And what do you think you're trying, what do you think is going on for you? In my brain, it's like, you sure? In my brain, it's like the little, the angel and the devil on my shoulder and the devil's like, do it.
8:57Simon Sinek:And the angel's like, do you want to do this? You sure? And 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. Where I'm like, hey, remember I said I was going to do that? Yeah. And the lesson that I have learned, and I'm better than I used to be, but the lesson that I've learned, and this, I think, is the first lesson to combat people-pleasing, I think is people are actually very comfortable with a no up front and it's and how do I clean that up?
9:42Simon Sinek:I don't fuck that right? What I've learned is like if you just tell somebody no up front 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. Mm-hmm. There's something in our system that believes, like, the world will end if I say no. If I say no. And I think, like, the, like, calculus there, or if I'm trying to, like, unwind the inner logic that's going on in my head, there's a part of me that's like, well, that'll just be future Alex who has to deal with.
10:18You know, like, present Alex wants the easy thing, but it's kind of like you're hungry and you want to eat junk food. Yeah. You know, you just, like, want to, you're like, okay, I want to eat all the, I always want to eat all the shitty food, but then you know you're going to feel bad later. you know it's not going to impact your health in the long term.
10:31Simon Sinek:One of my close friends, Kim, her mantra, and I try and remember it, if it's not a heck yes, it's a heck no. You know? Yeah. 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? They're like, yeah. Future Simon would love to do that. It 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. I think that's a really useful thing. I think I personally struggle with the, going back to the heck yes, heck no.
11:07I 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.
11:22Simon Sinek:I personally. It's not a heck yes, it's a heck no. Yeah. So what you're saying is it's fine in theory, but things are grayer than that in reality. Yeah. Including our own. 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. It's 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. So when you teach, people come to your stop people-pleasing class and I'm very curious, obviously you go around the room and you ask people to describe their experiences.
12:02Simon Sinek:I'm very curious what patterns you've noticed. Is there one kind of people pleasing, four kinds of people pleasing, infinite numbers of people pleasing? What do you hear in the classroom? It's a really good question. There's so many different types. I think one big one is a conflict avoidant people pleasing, which is any tension, any rocking of the boat feels like it's the world is ending and so i'm going to 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 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 good job um and And you'll do anything to get that.
12:54You'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 have 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 those three things scratch a lot of our like core human needs.
13:30Simon Sinek:There's a very important nuance here, which is you said addicted to the approval. I think everybody wants to know they did a good job and everybody wants their bosses to recognize them. And it's healthy to want it. It drives a lot of us to do good for those we serve and want to make them proud, especially if it's a good boss. We really want to make our leader proud. They've invested in us. We want to show them the investment was worth it. But that's not what we're talking about here. We're talking about the addiction to it, the need, which is it stops being about the work and it starts being about the approval.
14:06Simon Sinek:And that's an important nuance. I totally agree. And I think it's about 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, can you, so give us an, give me an example of that.
14:40I have 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, um, 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 and you're consistently not doing regularly not
14:58Simon Sinek:coming home in order to make do good do right by your boss not even do right by your boss do whatever needs to do to get your boss's approval you're you're sacrificing weekends nights family yeah again as you said not occasionally but habitually yeah and over time my experience has been that that's led for me 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 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.
15:47And 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.
15:56Simon 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. Yeah. 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. Yeah, to me, that screams like invisible self-betrayals, like where you know in your system that you're betraying yourself over and over and over again.
16:37Simon Sinek:Because you don't want to let them down. Yeah. Oh, they're in pain. They're angry. They're sad. Yeah. You know, they need somebody to talk to. Yeah. I don't want to upset them. The image that I always think about is, you know, the game Jenga? Where you stack the bricks. Yeah. Like, it's like if your sense of self is this Jenga and each time you betray yourself, you're like taking out one brick. Oh, great analogy. You're taking out another brick. Each time you say yes to something. Each time you over-apologize. Yeah. Each time you rescue someone else because they can't do the thing that they need to do.
17:05It's like brick, brick, brick, brick, brick. and then all of a sudden your whole life is unstable.
17:10Simon 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 out at a time, but eventually if it's habitual, it has consequences and it's going to collapse. What about you? How do you feel like you've seen people pleasing show up at work? 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.
17:52Simon Sinek:And they've, I don't know where it comes from, but they have to communicate hyper competence at all times to everyone. 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, 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 hypercompetence, but it's maintaining the image they've projected to everyone else of hypercompetence. 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.
18:30Simon Sinek:And the problem is, is they are. The problem is, is they actually are. It's 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 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 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?
19:20Simon Sinek: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. Lying. Lying is the wrong word. They're deceiving me and or themselves. The point is, is like even a well-intentioned leader who really wants to check in with somebody and 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 can actually find out what's going on so that we can intervene even if they say yes.
20:16Simon Sinek:So if they say yes, I can do it and I go, you know what, don't worry about it. I got this, you know? It's so hard 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? But that's hard too, right? It's hard. Because what if you just doubt somebody who is competent? Yeah. And so it's, I mean, 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.
20:44Simon Sinek:You know, none of this is crystal and clear. It's hard. Yeah. I think to your question of, what was your first question? I just want to, number one was, how do we offer practical things to the people who are the people pleaser but also how do we offer practical things to people who work with people pleasers? 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 what's going on in my system when I'm saying yes to 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 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.
21:29For me, one of the greatest myths about people pleasing is that somehow it'll work. You know, like you really think it's going to 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.
21:44Simon Sinek:Oh, thank God you're on the team. Yeah, yeah. Like, oh, you are so confident. At least somebody is. Yeah. And like, oh, that's so-and-so. Like, she's really like this, you know? And so that, or in, let's say you're... And that's the addiction part, right? That's the addiction, yeah. Let's say you're fearing the conflict. 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. But by the way, like any addict.
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22:10Simon Sinek:Yeah. Like, you know? So it's very consistent. And what's so interesting is that 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 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'm a good person.
22:56I'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 that 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 i mean let's be very blunt and let's be harsh and i say this with love okay what are you gonna say not to you okay um but
23:35Simon Sinek:people pleasing not making people please and not saying yes but we talked about it as jenga yeah but the the uncontrollable urge to 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, but probably both actually. But it's the desire for the approval that you become addicted to.
24:12Simon Sinek:and 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 try and... And 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 what how and by the way those are like hey i can help you like you know if you haven't made the deadline it'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've 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 exaggerating the point to make the point, but all because of the selfishness of the desire to get that approval and make somebody else happy in that moment, it actually becomes not the selfless act you think it is.
25:23I think I resonate with what you're trying to say. I think for me, labeling it as selfish, to me, activates the shame part of my mind, which for me shuts down my capacity to engage with it in a self-confusion. I said it was being 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 i'm it's probably some protective thing from my childhood probably some time in my childhood i had to internalize that i couldn't both be myself and be safe and accepted by someone else And so I picked being safe and accepted by someone else over staying true to what I know my needs are.
26:08Simon Sinek:That's a much better way of putting it. Thank you. You're right. 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 and doing all these things you know maybe I am a people pleaser I realize you know I've I've I've had to learn to say no yeah because I ended up hurting myself and others because I just, I became, I became unreliable.
27:00Yeah.
27:01Simon 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 on, 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 yeah 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 yeah or if you if I can if I can take something else off my list.
27:44Yeah. It's like also zooming out and being able to see the picture.
27:46Simon Sinek: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. Yeah. 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. Yeah. By the way, saying no to everything is also unreliable. Yeah. Because Because that's also not managing expectations because I have to do something. 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 and of time.
28:28Simon Sinek: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 yeah and it was always a desire to to be a great team player yeah um 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. 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.
29:05It sounds like that's the journey that you were on is you were saying yes to all these things and then you weren't able to follow through. Then you felt disappointed.
29:12Simon Sinek:Or I was putting myself in horrible positions where I'm just working too hard for fear of, you know, being unreliable. Yeah. And I think people who have the 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 um 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 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 she when we would work together and she would show me stuff and i could i would ask a question because 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.
30:27Simon Sinek:I mean, she'd 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, 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, I even remember where we were. We were on a plane on a business trip together and something didn't make sense.
31:04Simon Sinek:Something wasn't aligning. And I said, what happened here? And she sort of like, oh, 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 nothing happened. And very high performer. It's one of the reasons she was a high performer. 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 hit me forever. And then instead of the worst fear being confirmed, you have an opposite experience.
31:40It 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. That's what happened. Yeah.
31:48Simon Sinek:It didn't happen immediately, but it didn't happen over the course of time. She had to dip her toe in the water to discover. And so like when we think about if you work with a people pleaser. Exactly, yeah. Right? Which is, and I remember, because I couldn't just tell her. Like telling her isn't enough. And she wouldn't believe me. You know, I'm like. Or maybe she would believe you on a rational level, but something in her system would still fear it. 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.
32:21Simon Sinek: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.
32:58Simon Sinek:Ah, man, I screwed that up. It's such a beautiful thing. And to me, you executed it with so much love and grace. And that's also, 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. 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?
33:33Simon Sinek:But a positive corrective experience is, which is I am correcting something here. I'm correcting behavior, but it's gonna be such a positive environment for you that you will find yourself craving it or at least being okay with it. 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 this sense of safety so she knows that she can come to me. And instead of withholding information out of fear, she can be honest.
34:06And 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 gonna be okay. I just really wanna know. I trust you. and it's going to 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 going to be abandoned or I'm going to be rejected or I'm going to let someone down. I'm going to disappoint them. I'm going to have this fear. And then instead of confirming the old fear, the old belief, then I give her this other experience.
34:38And 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 over the long term.
34:53Simon Sinek: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 just started ignoring the emails. The problem is 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. And now we're reinforcing the negative corrective experience. Okay, I screwed up, but look how it's going. So I'm certainly not going to admit anything could go ever wrong again. What that does is just amplifies the shame. It just amplifies the shame. And being stuck in the shame spiral is not going to help you get out of the behavior.
35:26Simon 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? What do you mean? I'll prove it to you. You ready? You ready? Yeah. Don't think of an elephant. Ah. Right? You can't tell the human brain not to do something. Yeah. 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.
35:56Simon Sinek: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 and a safe environment if you tell me. 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. I love that. I've never heard that before. It's a good one.
36:27It's good.
36:29Simon Sinek: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? 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 gonna do it no matter what no matter what because it's a practice it's a practice and it's building the muscle of and you learn when to deploy it later but right now do it in extreme yes because the knee-jerk answer is always yes you know and in the moment it feels like an authentic yes.
37:12And so creating a little bit of that distance of just for 24 hours or for two hours or whatever it is, I'm going to actually check in with myself and I'm just going to see, 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 see 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.
37:32Simon Sinek:Sharing the dilemma, go on. 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. Sometimes we can share something other than a yes or no, and that can be truer 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.
38:04That'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 is it this thing then we like don't answer and we like fear we fear we either say yes or we don't answer instead of saying very simply like I don't know 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.
38:39Simon 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. 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.
39:12So 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 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.
39:37And so I try to share kind of like the big picture view and it creates the sense of togetherness. 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 OK. 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.
40:09And that is the beauty of sharing the dilemma. It starts a conversation. It starts a dialogue to find something that works for everyone.
40:18Simon 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 want to say you want to avoid saying I don't want to say no right because now what the person who asked you just heard is like okay you're about to you're just telling me no yeah right 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 yeah that's not making the other people the other person feel affirmed and asking for help it would sharing the dilemma it would as I'm learning from you I'm sort of gaming it out in my own head I need you to do this ah yes that needs to get done um i'm working on this and i've got this um 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 yeah of trying to solve the problem they're asking you to solve by moving 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 say yes, I want to make sure this happens, but I don't want to say no.
41:30Simon Sinek: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 yeah 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.
42:19We 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...
42:27Simon Sinek:It's not negating. 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 accept, I have to think that this. I think there's a nice trick, because I do this as well, which is I say to my team, I'm thinking out loud here. That's a different reason. it comes from, you know, people who think out loud. The addiction of thinking out loud. No, no, it is. But people, especially 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?
42:57Everything's a muscle.
42:58Simon 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. Or even like, yeah, I'm in a little pickle. These are the things that I think about. Yeah, pickle, dilemma is like, I think the device of 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. I love that, yeah. What else? This is so good. Another one that I love. Okay, have you heard the term villain era? Villain era, E-R-A or E-R-R-O-R? E-R-A. Villain era.
43:39Yeah. Like the era of villains. It's kind of like a modern term.
43:41Simon Sinek:No, I don't know the term villain era. It's like when you're... Isn't that an album by Taylor Swift? Maybe. That's too modern for me. One of her eras? Have you heard of the term villain era? I have not. Is this modern slang? Is this about to make me feel old? It's probably going to make you feel old. Okay. But maybe to other people listening. Is this on fleek? Wait, that's old. I wouldn't go there. Sorry. Okay, so a villain era is a modern term. Yeah. And it's basically when you move from being overly accommodating, like nice to everyone, people pleasing, prioritizing everyone else's needs over your own, to like I'm prioritizing myself and I'm not going to say yes to things that I'm not a yes to.
44:26Simon Sinek:So basically you're handing in your wings and your halo and you're trying out the horns for size. Exactly. You get it. 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. Okay. 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, 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.
45:03and 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 are you advocating for villain errors or are you not advocating for villain errors 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 do you
45:31Simon Sinek:You have to tell people. I like to tell people. That way they know what's going on. And also maybe they'll even be on my team. Because otherwise you're going to start acting differently and people are going to be like, what the hell? And now they label you the villain. Exactly. So I try to name it in a way that 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, I just want to let you know that I'm working on this.
45:57I'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 maybe will you check with me when I say yes to something? Will you check and say, are you sure? 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.
46:30and 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.
46:44Simon Sinek:The thing, 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, 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 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.
47:18Simon Sinek: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 going to be practicing one I'm going to start saying let me get back to you when you asked 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.
47:52Simon Sinek:The other one is I'm going to share the dilemma when you asked 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? Yeah. Or if I, 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 you know so I think getting the 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 yeah which is only a good thing and and uh I and I really like that and it makes it makes the other person complicit in your success yeah I like I love the way you put it of 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 people pleasing isn't just my problem yeah we all have our issues you know um 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 is when everybody agrees to grow together.
49:12Simon Sinek: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, I'm going to try and make up a term like your positive corrective environment, which is affirmative deadline adjustment. Affirmative deadline adjustment? Yeah, or ADA. Nothing like a good TLA, three-letter acronym. Yeah, so affirmative deadline adjustment. So I'll give you real life scenario. Hey, Simon, can you do this? Yes. I need it 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.
49:56Simon Sinek:And I call and be like, I can't do this by Friday. And it's probably Friday morning. I can't do this today. and they're like, that's fine. Anytime next week will do. And you realize when you say, when do you need it by? People just make shit up. Everything in working is made up. 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 it by?
50:34Simon Sinek:Friday. is next Tuesday okay? Yeah, next Tuesday's fine. And I found out that very few deadlines that I was given are actually deadlines of which there were 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, it's so good. And it's also the opposite of what's normally happening, which is like, oh, the whole world is caving in on me. Well, you just assume that whatever you're being told is like the thing.
51:11Simon Sinek: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. 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 going to hit the deadline because there are serious consequences.
51:45Simon Sinek:So anyway, different conversation. Are there any other tips for people pleasing, either for the people pleasers themselves or for people working with people? 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. The third one was asking for support and getting help in what you're working on. And the fourth one is confirm the deadlines. Confirm the deadline.
52:22Simon Sinek:Don't just take it for granted that whatever the deadline is, is actually the deadline. Or the workload or whatever it is. Confirm the thing that needs to be done. 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 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're like overly firm and aggressive sometimes or overly mean because we just think that that's what we need to do.
52:59We 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.
53:05Simon 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. Yeah. And there's no quicker way to disingratiate yourself on a team than saying these are my boundaries and I'm not. 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 helps you work to your natural best and it manages the expectations of the people with whom you work.
53:47Simon Sinek: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. So 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 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.
54:21Okay, are there any other strategies or things?
54:23Simon Sinek:I learned this from the Air Force. in private sector it's very this is a normal scenario somebody works really really hard on their PowerPoint presentation they work two weeks on it and they have the big meeting and they do their presentation and at the end they go pretty good right 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 their 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.
55:04Simon Sinek:Whoa, I love that 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.
55:45Simon Sinek: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 is that this culture of spears has allowed them to experience getting negative feedback and not feel bad. Yeah. And the stakes are low, right? It's like exposure therapy. 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 sets the, and everybody sees the meetings. Like, everybody's like, yeah, good Spear, good Spear, you know?
56:24Simon Sinek:And so all this negative feedback that's being thrown at the work, people are seeing we're not attacking you. Yeah, it's like oriented towards growth. We're helping the work. Yeah. It's always at the work. It's never at you because I think people pleasers very often confuse that the criticism of the work is criticism of me. Yeah. It's not. Yeah. It's of the work. And Spears clarifies that. I love that. Yeah, it's great. Yes. There's five techniques. Okay. 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.
56:57Simon Sinek:Number three, ask for help. Yeah. Tell someone that your behavior is changing. Tell someone your behaviors are going to change and to support you and even sometimes prompt you with scene number one and two. Yes. Number four... Affirmative deadline adjustment. A really well-named... It's terrible, isn't it? Behavior. It's terrible. Let's just call it like check the deadline. Number four, check the deadline. And number five, ask for Spears. Proactively ask for Spears. 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.
57:34Simon Sinek:I love it. But more importantly than us feeling pleased, I really hope that everybody's listening is feeling pleased. Until next time. Until next time. Thank you, Simon. Thank you, Alex. 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 simonsynic.com. Thanks for listening. Take care of yourself. Take care of each other.
From the publisher
Welcome to Feelings at Work, a special series from A Bit of Optimism with Simon Sinek.
Work isn't just about deadlines, meetings, and getting things done. It's also where we experience frustration, excitement, trust, anxiety, belonging, conflict, and joy. If we want to build healthier teams and better workplaces, we have to get better at understanding the emotions that shape how we work together.
That's what this series is about.
In each episode, Simon Sinek sits down with Yale professor and Lifeshop founder Alex Simon to explore one emotional challenge that affects how we work, lead, and relate to one another. Together, they unpack the emotional skills most of us were never taught—but use every single day.
This episode is about saying yes.
Have you ever agreed to something... and immediately regretted it?
Maybe you didn't want to disappoint someone. Maybe you thought, I'll figure it out somehow. Maybe your calendar is packed, your to-do list never gets shorter, and somehow you're still worried you're letting people down.
Most of us don't think of ourselves as "people pleasers."
We just want to be helpful. We want to be dependable. We want to be someone others can count on.
But what if constantly saying yes is actually making things harder—for you and everyone around you?
Together, Simon and Alex explore why so many thoughtful, capable people take on more than they can realistically handle. They unpack the hidden patterns that lead to overwhelm, resentment, and burnout—and why trying to keep everyone happy can quietly make us less reliable.
The good news? This is a skill we can learn.
In this conversation, you'll discover practical ways to communicate more honestly, set healthier boundaries, and build stronger relationships—without feeling selfish or letting people down.
In this episode you'll learn:
➡️ Why saying yes too often can actually make you less reliable
➡️ The hidden connection between overwhelm, burnout, and self-betrayal
➡️ The simple phrase that creates space before committing
➡️ A better alternative to saying yes or no: how to "share the dilemma"
➡️ What leaders can do to create teams where people feel safe telling the truth
➡️ Why healthy boundaries strengthen relationships instead of hurting them
Whether you call it people pleasing or simply trying to keep up with everyone else's expectations, this conversation is a reminder that taking care of yourself isn't selfish.
It's one of the best ways to show up for the people who matter.
This... is A Bit of Optimism.
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Chapters
Chapters
00:00:00 Why We Need to Talk About Feelings at Work
00:02:00 What People Pleasing Actually Looks Like
00:04:20 Why People Pleasing Hurts You and Your Team
00:07:00 Why We Say Yes When We Mean No
00:10:00 Different Types of People Pleasing
00:13:00 Why Approval Can Become Addictive
00:15:00 How People Pleasing Leads to Burnout
00:18:00 The Hidden Cost of Being "Hyper Competent"
00:21:00 Why People Pleasing Doesn't Actually Help People
00:27:30 Simon's Experience With Saying Yes to Too Much
00:31:00 How Leaders Can Help People Pleasers
00:38:20 The Power of "Let Me Get Back to You"
00:40:00 How to "Share the Dilemma"
00:44:00 The Difference Between Being Reliable and Being Available
00:47:00 Building Healthier Boundaries at Work
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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
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About Alex Simon
Alex Simon is a Yale professor and the founder of Lifeshop, a school for adult emotional education. 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.




