How Middle Managers Can Become True Leaders | Full Conversation

My Notes

• No one wants to be managed, people want to be led → present yourself as Engineering Lead, not Manager
• You don't need to be everyone's friend. You have to be friendly. And trying to be friend with everyone actually undermines your #leadership
• #communication/tip answer questions "what should i do", with counter question "what do you think we should do?" → this teaches people to be self-reliant
• be confident and vulnerable. Don't be weak and vulnerable → eg. there is difference how you use your voice when showing vulnerability
• it's leader daily job to "push push push" people… but with love!
• #communication/tip start meetings with statement: "here is the challenge, now please tell me what you think"… shut up, and be quite, quite → be confident with the silence, and dont ask "anyone, anyone, anyone" → its resets their thinking
• #communication/tip and finish meeting with saying: "i came to this meeting with this point of view, but i can say, i changed my mind.,…"
• ask teams "what sucks, and what sucks less" → kinda retrospective → 31.06. Team Retrospectives
• good #10x-leader test: check whether his team calls him "the leader" or "our leader" → do they took ownership of their leader or not? they should and therefore they will call him "our leader" which will allow them to challenge him directly
• 3 traits of great leader? #10x-leader
  • 1. courage → courage to be open about my weaknesses → courage to go against the "power" → courage to tell somebody what may hurt their feelings
    • → courage is usually external (eg. parachute for jumping off the plane) → you don't need to find courage down inside of you→ somebody or something will give you the courage → so you just need somebody who will tell you i trust you, i believe you and if anything happen i will be there for you.
  • 2. integrity
  • 3. being student of the communication → listening in a way that people are heard + speaking in a way that people can hear you (as opposite to triggering them, etc)
• the #10x-leader is person who goes against the fear, against the danger, and first speak about your weakness (being vulnerable), and this courage they have makes them lead (/ good leader)
• as a leader i don't need to know all the answers and i don't need to pretend i know all the answers → your credibility is NOT built with that

AI Summary

Main Idea of the Text

The text is a transcript of a conversation between Simon Sinek, an acclaimed author and motivational speaker, and Taro Rabu, VP of Engineering, moderated by Sophia Chova, VP of People Strategy. The discussion predominantly revolves around the theme of leadership, distinguishing between managers and leaders and highlighting leadership as a responsibility rather than a rank or position. The key focus is on cultivating leadership as a skill, emphasizing the importance of continuous learning and psychological safety in fostering innovation and trust. It also delves into creating an environment that supports challenging the status quo, promoting a culture of trust and integrity, and recognizing leadership as an ongoing journey rather than a static state. Practical illustrations and anecdotes are shared to elucidate these points, emphasizing the human-centric aspects of leadership and the need for creating conditions in which individuals feel safe to express vulnerabilities and exchange feedback openly.

Notes

• Leadership is a responsibility to foster others' growth, differing from management, which involves oversight of processes.
• Effective leaders create psychological safety, enabling team members to feel secure in expressing mistakes and uncertainties without fear.
• Learning and developing leadership skills is continuous; it requires reading, discussions, and dedicated practice.
• Leaders should exemplify integrity and courage, instilling trust by admitting personal limitations and encouraging honest communication.
• Creating a "challenge culture" within teams can enhance innovation by allowing team members to safely push boundaries.
• Trust-building is a gradual process, akin to developing any skill and begins with leaders modeling desired behaviors.
• Leaders should communicate transparently during crises, acknowledging changes in management style as temporary responses to stress.
• Encouraging leaders to cultivate accountability empowers teams to take initiative and learn from missteps.
• Shared forums or activities, such as cross-departmental projects, can bridge gaps between different organizational disciplines.
• Facilitation skills, such as listening and offering constructive feedback, are vital for effective leadership.

Main Ideas and Explanations

1. Distinction Between Manager and Leader:

   • "People wake up in the morning and they want to be led...leadership is a responsibility."
   • Important for understanding the essence of leadership as an influential human function beyond procedural management.

2. Leadership as a Skill:

   • "Leadership is a skill...the skill must be studied."
   • Highlights the necessity for ongoing learning and development of leadership capabilities.

3. Psychological Safety:

   • "Psychological safety is very simple; it means that I feel safe to say I made a mistake..."
   • Essential for fostering open communication and trust within teams, which can improve collaboration and innovation.

4. Trust and Integrity:

   • "The few things I’ve seen universally about the great leaders, number one, is courage...integrity."
   • These qualities are crucial for building authentic relationships and environments where team members feel secure.

5. Cultural Impact of Leadership:

   • "Most important is the culture you create in your sphere and then it ripples."
   • Acknowledges how leadership influences organizational culture and its spread throughout departments and teams.

Actionable Ideas

1. Embrace Continuous Learning:

   • "All the best leaders I’ve ever met study it...they never think of themselves as experts."
   • Leaders should read, engage in discussions, and constantly refine their leadership style.

2. Develop a Challenge Culture:

   • "License to challenge...psychological safety...can unlock innovation."
   • Encourage team members to challenge existing norms safely to foster innovation.

3. Admit Vulnerabilities:

   • "The confidence to say I don’t know."
   • Leaders should model vulnerability to encourage openness within their teams.

4. Set Clear Expectations:

   • "Go back to your teams and say...you’re going to see me experimenting with techniques and strategies."
   • Transparently communicate leadership development efforts to align team expectations.

5. Cultivate Accountability:

   • "Tell my team, 'Hey, I’m gone for a week...you’re accountable, not me.'"
   • Delegate responsibly and let team members own decisions to build trust and independence.

Summary in Outline Form

1. Introduction

   • Purpose of the event and introduction of speakers.

2. Discussion on Leadership

   • Difference between management and leadership.
   • Leadership as a skill requiring continuous learning.

3. Creating Psychological Safety

   • Definition and importance in teams.
   • Practical steps leaders can take to foster it.

4. Qualities of Effective Leaders

   • Courage and integrity emphasized.
   • Leadership as a relationship built on trust.

5. Cultural Influence of Leadership

   • Strategies for promoting interdepartmental collaboration.
   • Encouragement of open communication and feedback.

6. Addressing Leadership Challenges

   • The role of trust and integrity in leadership.
   • Techniques for breaking down organizational hierarchies.

7. Final Reflections

   • Courage and vulnerability as cornerstones of effective leadership.
   • Importance of leadership adaptability in crisis situations.

8. Conclusion

   • Open Q&A session reinforcing core concepts discussed.

Footer Notes

• Self-promotional content from the introduction and conclusion has been omitted.

Transcript

Speaker: Sophia Chova: hi everyone I’m so excited to welcome you to leadership lab my name is Sophia Chova I’m the VP of people strategy and I wanted to first start by saying thank you for taking the time to come to our first leadership lab please join me in welcoming Simon Sinek who’s an award-winning author and speaker and our VP of engineering Taro Rabu to the stage to will be interviewing Simon Sinek and there will be time for some questions please give them a warm welcome.

Speaker: Taro Rabu: I appreciate the warm welcome, Sophia, and I’m grateful to be here. It’s great to be here with you, Simon.

Speaker: Simon Sinek: It’s nice to be here with you, awesome, awesome. Alright, so I’m going to start with some questions. Um, throughout these questions I’m going to attempt to intersperse a bit of my experience and perspective as a way of reflecting some of the things that I imagine my colleagues here are going through and perhaps we punctuate with some Q&A at the end. Perfect.

So early in my career I felt like leadership is basically the way that you treat others like you know just how you act. Um, I think I’m a nice guy and that’s how I showed up based on those principles until I met a manager of mine, his name is Grant English, who said, “No, no T, listen you gotta study it like a science.” Right? Um, that said I’m curious, you know, your take on the distinction between manager and leader, right? You know it resonates with me personally, so what’s the difference and what does it look like to cultivate leadership as a skill?

Speaker: Simon Sinek: Great, great question and I think that this is about pushing and challenging each other and this becomes your first challenge because you introduced everybody as people managers. Uh, but the problem is, is no one wakes up in the morning and wants to be managed.

Speaker: Taro Rabu: Totally.

Speaker: Simon Sinek: Yeah, people wake up in the morning and they want to be led. Yeah, and the reality is you can’t manage people. You can manage a process, you can manage a project, you can manage a schedule, but you lead people. It is a human function. Yeah. Um, and the best leaders that I know, uh first of all—like I said—usually we treat management as a position or a rank in an organization but leadership is a responsibility and it’s the awesome responsibility to see those around us rise. Yeah, and you are right because leadership is a skill. Uh, number one is we have to learn it. Most of us do the jobs that we’re good at and we probably had some sort of training along the way. We may have gone to school for engineering or being a lawyer or whatever it is, or if we didn’t, the company will give us on-the-job training and they have—most companies have pretty sophisticated training programs especially for junior people. Why? Because they want us to be good at the job. That’s why they look at our grades and how we did at school or how we’re doing in the training program and if you are good at your job you will get promoted and you’ll eventually get promoted into a position where you no longer do the job that you were trained to do. You now have to do a new job called leadership, and we often get little to no training on how to do that job. So you’re 100% right, it’s a skill and the skill must be studied.

Speaker: Taro Rabu: Interesting.

Speaker: Simon Sinek: Sometimes, and I expect that the company offers formal training as leaders their way up the ranks uh but also we have to take responsibility and all the best leaders I’ve ever met study it. They read books, they read articles, they watch talks, and they have conversations about it constantly. They are fascinated by it because it’s the thing they’re trying to learn and they never ever think of themselves as experts; they always think of themselves as students.

Speaker: Taro Rabu: Amazing.

Speaker: Simon Sinek: The piece around people managers as a bit of a misnomer as to what we’re trying to achieve here is it actually resonates. So perhaps that’s a big thing—everyone here is a people leader and maybe we strike that from—and as a follow-up I’m curious around this notion that management becomes an ascension from a perception standpoint, but what about leadership? And is that in the domain of people managers?

Speaker: Simon Sinek: Yeah, solely. So there’s formal rank which affords you authority but leadership has nothing to do with rank. Yeah, as I said before, leadership is the awesome responsibility to see those around us rise. And people will only follow you if they trust you and feel like you have their back. They’ll do as you say because you have authority over them or they may have fear. Yeah, but respect and psychological safety that leads to followership, which is when people give you their blood, sweat, and tears, partially because they want to do right by the company but largely because they want to make you proud. Uh, and so the question is what conditions do you have to create that somebody would want to do something for you willingly and wanting?

Speaker: Simon Sinek: So just to go off in a little tangent if you're interested in this kind of thing you can always interrupt me. By the way, I’m like a windup toy—you just put a coin in it. I’ll do my best.

Speaker: Taro Rabu: Got it.

Speaker: Simon Sinek: So you can just as a quick aside, you’ll appreciate this. So we’ve all been in meetings where um somebody is talking, they’ve made their point but they just keep going and going and going, and we all feel bad because we don’t want to interrupt and we don’t know how to interrupt or when so we just sit there. Or is this cue for me to interrupt you, Simon?

Speaker: Taro Rabu: Yes, but.

Speaker: Simon Sinek: Or we go off the reservation and we’re making a different point and again, same thing. So in our company we came up with a thing called “banana” which is if somebody made their point, anyone in the room can just say banana which means we get it, let’s move on. And it’s a very polite way of interrupting, so you can banana me anytime.

Speaker: Taro Rabu: You got it!

Speaker: Simon Sinek: I will work, I’ll do my best to banana you and others here as you go on. So I was going to say how the psychological safety is created and what the actual anthropological responsibility of a leader is really quickly because I find this interesting. Um, way back when—caveman times—uh, human beings lived in populations that were rarely bigger than about 150 people. That was about the size of a tribe, right, give or take. But that’s where it maxed out in that range. Um, we had to help each other, we had to work together because as human beings by ourselves we’re not strong. I can’t kill a cyber saber tiger, defend myself against a woolly mammoth by myself— not gonna work out.

But as a group we are absolutely remarkable. We have to remember that we’re social tribal animals. Our survival depends on each other. Which means if I go to sleep I have to trust that you will watch for danger, perfectly good system, and vice versa. Um, we’re constantly assessing and judging in our society who’s alpha, right? Um, so if you’re the strong one in the tribe you can shove your way to the front of the line to get the food. If you’re the artist in the family you get an elbow in the face—this is a bad system. Because if you punch me in the face in the afternoon I’m probably not going to wake you and alert you to danger, right? Bad system.

So we evolved into hierarchical animals where we’re constantly assessing and judging each other who’s alpha, right? And it can be based on whatever. Depends on the population you know uh, on what we consider alpha status. And when we assess that someone is more senior than us in the organization, we voluntarily step back and allow the alphas to eat first, right? So no elbow in the face and I’m guaranteed to get some food. Now the thing is we’re not stupid, right? We don’t give our alphas first choice of meat and first choice of mate for nothing; there’s a deep-seated social expectation.

Speaker: Taro Rabu: Alright, so next question.

Speaker: Simon Sinek: So, Simon, the leadership lab that Sophia mentioned has—as she discussed—a Q3 topic called “license to challenge,” right? Which is we’re thinking about it as a form of psychological safety, and the belief here is that it can unlock innovation in our teams. We want to hear from them; we want them to throw out bananas and let us know when things are going awry, right? That’s the spirit. Now however, when we say psychological safety it can very well mean different things to each of us. For example, I could say, isn’t that simply just being nice to—we’re all nice to each other, we do that, we know how to do nice—Etsy nice, as we call it, right? Um, can you help unpack that for us? Like what is psychological safety truly and what is it not? And why is it so fundamental to success?

Speaker: Simon Sinek: Yeah, it’s nothing to do with someone’s personality, uh that’s number one, right? Okay, um I’ve been in organizations that are so nice but they’re so nice that they’re passive-aggressive, that nobody gives you any feedback and nobody tells you anything because nobody wants to offend you. And as a result, people’s careers just sort of float—they just sort of live in The Ether because nobody gives me feedback, right? So nice can go too far.

Um, psychological safety is very simple; it means that I feel safe to say I made a mistake or I don’t know, yes, or I’m struggling at home and it’s affecting my work, or I’m scared—without any fear of humiliation or retribution, without any fear that it’s going to affect my career. In fact, I can say these things with confidence that the team and my leaders will rush in to support me. Yeah, we’ve all been on teams that have that. We’ve also been on teams—all of us—where you would never admit a mistake or say you don’t know because you fear public humiliation or being, uh, having it hurt your career. And so we spend our days lying, hiding, and faking. Yeah, so psychological safety is very clearly the feeling safe to say those things.

Speaker: Taro Rabu: I love that. And you know, as a lead-up to this meeting or this conversation that we’re having, um just as a proof point I was super nervous, as I told you—and folks who know me will be like “Oh, that’s nonsense”—to um, but in admitting that a lot of improvements and tweaks were made along the way. I got this little clipboard from Andrea—she said, “Hey, I’ll print it out for you, pal. It’ll be okay.” Um, I got some pep talks from like my peers here like, “You know T, you can do this.” I’m like “Okay, maybe 10-15 minutes in we’ll see.” But I got you too, T.

Speaker: Simon Sinek: Yeah. And I love that because you know the notion of it being an abstract thing—and you can’t connect it to real-world examples—and we don’t want to talk about what the benefits of it I think is worth mentioning. So I love the example and thank you for framing that in that way especially the feedback piece.

Um, so that’ll segue into my next question. So when I think about psychological safety, I believe that trust is a key piece, right? To this right, which makes coaching and feedback, as you mentioned, um, much more productive. So like what’s your take on what psychological safety looks like when it’s done well, um and the inverse is what are signs that it’s going starting to grow within a team?

Speaker: Simon Sinek: Sorry, so the question you’re asking is not dissimilar to how do I make a friend or how do I build a relationship, which is clearly you can’t go on a first date and have trust and ask for a hand in marriage—it’s ridiculous, right? Um, but, and the dance that we do in building friendship and building trust in our personal lives can be somewhat short and somewhat long, but it’s not instantaneous, ever. And it’s the same at work; there’s no single decision that you can make or one thing that you do that all of a sudden everybody loves you and everybody comes along at a different time— even on your own team, right?

Right, we don’t know what people’s previous experiences have been. So there’s a few things we have to remember, which is it’s a process and it’s a little bit like working out, which is you know you’re asking how do I build trust. I’m saying, okay if you want to work out and get into shape, you’re gonna have to do chest, you’re gonna have to do arms, you’re gonna have to do legs, you’re gonna have to do core, and you’re like great where do I start? I’m like yes, just pick one, it doesn’t matter. You’re gonna have to do it all, right? It’s the same thing.

I’ll give you some pointers; there are many other things, but just it doesn’t matter the order just please just do one, go. So number one, which I think is one of the most important things um and you demonstrated it, T, which is leaders have to lead by example. Just like children follow their parents, uh, people on a team will follow the example of their boss. If the boss lies, yells, screams, always has all the right answers, guess what you’re going to get from the team? You’re going to get pushiness, you’re going to get people jockeying to be right all the time, right? The leader will set the example.

Speaker: Taro Rabu: Got it.

Speaker: Simon Sinek: And so it doesn’t actually work when the leader says, um, “Hey, if you make a mistake or if you don’t know something, tell me! I’m totally cool. I’m building psychological safety here.” Till you do it, right, it’s not gonna work. What actually does work is when the leader says, um, “I don’t know. You’re asking me a question; I’ll be honest with you, I don’t know. I don’t know.” Or “I screwed up and I need your help to fix it.” Right?

Now people are afraid of doing those things because it is that word that scares a lot of people—vulnerable, right? Because it’s admitting weakness, but admitting weakness and being vulnerable are not the same thing, right? So I don’t want anybody to ever say, “Oh, I’m so nervous, I’m useless at this; I can’t, I don’t even know how—this is not going to go well.” Right? Like, that will not inspire confidence. Own it, be confident in the expression.

So for example, hey I have no clue what’s going on. I am so nervous, you have no idea. And unless somebody helps me, this is not gonna go well. Sounds familiar?

Speaker: Taro Rabu: Great, great.

Speaker: Simon Sinek: But listen to the tone of voice—it’s so different. Yeah, and if the leader goes first in pretty short order, you will find that people will start to take the risk to do the same per the leader’s example. And we have to welcome it, that if somebody says “I made a mistake,” we can’t say “What’d you do?” No! You go on, I got you. What do you need? If somebody says, “I’m struggling at home,” you go “It’s okay, don’t worry about it, we’ll take care of the work thing this week. Don’t worry about it.” You know, so we have to affirm those risks that people are taking.

Speaker: Taro Rabu: Amazing, amazing. So I’ve seen a bunch of your stuff and I love the stories that come out of like the material that you have, so do you have any stories of leaders that you’ve worked with who’ve done a great job of building psychological safety that you’re describing?

Speaker: Simon Sinek: Uh, I mean, one of the best leaders I ever had, young in my career, um, I was a junior. Uh, I think the official title was Junior Idiot, um, at a big ad agency. Um, I filled the specs perfectly, by the way. Um, and, uh, my—it wasn’t actually my boss, it was my boss’s boss, it was the big boss, uh, who ran the whole group; his name was Peter. And Tagio, one of the best leaders I’ve ever had in my life. Um, Peter I wouldn’t call him warm. He was very nice, but he didn’t exude warmth, you know?

Um, so that goes to that nice thing—the, you know, you don’t have to be everybody’s friend. Yeah. Um, you have to be friendly, but you don’t have to be everybody’s friend. In fact, that’s a different conversation; trying to be everybody’s friend actually undermines leadership, different conversation. But Peter never answered a damn question ever. Right? “Hey, Peter, what should I do? What do you think we should do?” You know, Peter, I’ve exhausted all the things; that’s why I’m coming to you. “Well, I don’t know. What do you think? Just tell me what you think.” He never answered a damn question. And it was at times excruciating.

Speaker: Taro Rabu: Yeah, right.

Speaker: Simon Sinek: What ended up happening is he taught me self-reliance. He taught me to think for myself, but he also taught me to bounce ideas off other people because if I had to go tell Peter—who’s my boss’s boss—what my idea was, I’d better be pretty confident that I’ve battle-tested it with a few people before he shoots all the holes in it.

Speaker: Taro Rabu: Yeah, yeah.

Speaker: Simon Sinek: So it taught me to ask for help. And this is I think one of the mistakes people make especially young people, because we tell them to be self-reliant and all this and they go and tell you their ideas because they want to prove but they haven’t battle-tested it and we shoot ideas and then they say “Well, you don’t provide psychological safety,” right? Interesting.

Speaker: Taro Rabu: So that’s our job, which is to push and push and push with love, with support; but at the same time, we’re holding them to high standards so they better bring good work to us. I don’t expect them to come with me to come to me with right answers. I expect them to come to me with thoughtful answers.

Speaker: Simon Sinek: Got it.

Speaker: Taro Rabu: So Peter was one of the best leaders I ever had and I don’t think he ever answered a question, ever!

Speaker: Simon Sinek: That’s fantastic!

Speaker: Taro Rabu: Alright, that’s it—no more answers! No more answers, yeah, just just questions!

Speaker: Simon Sinek: In spirit of questions, I’ve got another question. Um, now, good segue by the way, thank you, thank you. Um, so you described Peter and his penchant for asking questions as a way of sort of triggering that for you. Right now, what are some surefire ways in which a manager can extinguish psychological safety? Where are the minefields waiting for us?

Speaker: Simon Sinek: Yeah, so, um, there’s a great story that Nelson Mandela used to tell. Um, he was asked by a journalist—now, Nelson Mandela is a very, very important case study in the leadership world because he is universally around the world regarded as a great leader. Different people are viewed differently, depending on where you go in the world, but not Nelson Mandela, which is why he’s an important case, right? Because it’s universal. And he was asked by a journalist, “How did you learn to be an effective leader?” To be a good leader. And he tells the story. He told the story of his childhood; he grew up as the son of a tribal chief—his dad was a tribal chief.

Speaker: Simon Sinek: And he says, “I remember going to tribal meetings with my father, and I remember two things: they always sat in a circle and my father was always the last to speak.” Now, if you think about it, when we come into meetings the number of times we sit at the head of the table versus sitting in the middle of the table creates a hierarchy. That’s number one. As opposed to even on a rectangular table, you can create a circle, right? And you think of the number of times we come into meetings and we go, “Okay here’s the challenge we’re facing, guys. Even if it’s somebody who’s good and well-liked and all that, here’s the challenge we’re facing.” Um, I want to get your point of view; here’s what I think but tell me what you think.

Speaker: Simon Sinek: Yeah, too late! Too late! You’ve either biased the room or you’ve made people feel that their opinions don’t matter. So it takes a lot of discipline for our leader to say here’s the challenge—tell me what you think—and then shut up. And if it’s quiet, don’t say “Anyone? Anyone?” because people who are quiet need to think before they speak—not like me, who just thinks out loud, right? You’re doing great.

Speaker: Simon Sinek: Every time you say “Anyone?” it restarts the system. So you have to get comfortable with uncomfortable silence and someone will break it. And you have to be good at leading the room. Now what do I mean by that? Much is said in leadership about self-awareness; you have to be self-aware. I actually think that’s very difficult. I don’t know my blind spots; I don’t know how people receive me, right?

Self-awareness is actually very difficult. I think we have to practice situational awareness—that’s more important. Right? So that when you’re sitting in that room and you’ve asked for help, you’ve asked for ideas, one person’s doing all the talking—are you aware of that? Can you say, “Dave, love the ideas; let’s hear from somebody else”? Or are you in the corner of your eye? Are you looking at the person who goes, and you’re like, “Hey Stacy, you want to say something?” Yeah? Or somebody who hasn’t spoken at all, and at the very end you go, “Hey T, I know you have a point of view; I want to know what it is.”

Speaker: Simon Sinek: And the point is that a good leader isn’t leading the idea set; they’re leading the room. And by the way, the leader may change their mind, zero based on their original thoughts—but you’ll make people feel heard and you get all the benefit of all those new thinking. So you actually might learn something and actually might change your point of view.

Speaker: Taro Rabu: Wow, wow—amazing! Thank you for sharing that. And the takeaways here are again back to the skill—that there’s a lot of intentionality in what you describe. It’s not just like “Hey, just naturally hang out and high five or fist bump.”

Speaker: Simon Sinek: No, and it’s great that we have this series because I think it’s going to be valuable for a lot of us to be intentional about those things that you talked about—hierarchy, facilitating, and not leading in the traditional sense. So I love that. If I may—

Speaker: Simon Sinek: Yes, please!

Speaker: Simon Sinek: This stuff is difficult; it all requires practice. And you will rarely get it right the first couple of times. It is a process, like getting in shape, right? It is a process, you have to trust the process. Yeah, and of the people who are in that room, I highly, highly, highly recommend you find a buddy, at least one, or a peer group because it is too difficult to do this thing called leadership alone, right?

Speaker: Taro Rabu: Totally.

Speaker: Simon Sinek: It’s like even parents, there’s—you know, the traditional nuclear family has two parents, but even if you’re a single parent you still ask for help from your parents and your friends. You still get feedback and input. Leadership is the same—don’t be so foolhardy to think that you can do this all alone; you need the mechanism to say, “Oh, I tried it today and it freaking blew up in my face.” Even if it’s just a cathartic venting, make sure you have a leadership buddy.

Speaker: Taro Rabu: Amazing! Leadership buddy—I love the concept! Um, alright so following the SP side, um, we’re managers here—or leaders, if I will—to if I were to reframe it, they’ll all have an opportunity to learn about the different levels of psychological safety. Um, and the one to hone in on is a “challenge your safety” because it’s the highest form um that items should strive for.

Um, so—to impact that a bit, it’s um, it’s the goal here is to allow us to thoughtfully challenge each other and push the status quo, right? Um, but why is challenging so difficult for individuals? Um, what’s your assessment here? What makes it really hard to create a truly safe environment to challenge in that way?

Speaker: Simon Sinek: So there’s multiple reasons; it’s layered and messy, like just like people are layered and messy, right? Yeah, I mean some of it may have nothing to do with the leadership environment you’ve built; it may go back to somebody’s childhood— that they just got yelled at all the time by their parents, you know, for anything they said—they’re going to carry that baggage with them for the rest of their lives. And so, you know, it becomes difficult just sort of anti—their personality to do these things.

Speaker: Simon Sinek: Yeah, or we don’t know the companies they worked at before, you know, that you know once bitten, twice shy. So we have to be patient that everybody comes along at their own pace and it’s not bad or wrong and no one is failing if they’re not challenging, right?

So there’s a few things to remember and hierarchy plays into it, right? So for example, a Marine General friend of mine—he says his test for a good leader is—is if the group has taken ownership of their lieutenant—so is it the lieutenant or is it our lieutenant? Right? And that’s the first line leader. Now, the leader that’s seven or four lines away, it’s always the colonel; it’s never “our”— it’s always the vice president, it’s never “our” vice president, right?

Speaker: Taro Rabu: Yeah, yeah!

Speaker: Simon Sinek: Uh, and so challenge your culture—you’re going to get it very difficult; not because they’re bad people, not because they don’t challenge—there’s either respect component or an intimidation component.

Speaker: Taro Rabu: Interesting!

Speaker: Simon Sinek: I struggle with it on my own team, right? That I know my team challenges each other—I wish they would challenge me more!

Speaker: Taro Rabu: Yeah, yeah.

Speaker: Simon Sinek: So one of the things that I have to do is I have to push it and I have to invite it. So how do I do that?

Speaker: Simon Sinek: It’s like I’ll say one of my favorite tests is, “Okay what sucked and what sucked less?” If I made a thing, I’m say: “Alright, what sucked and what sucked less?” Right? Um, or can you tell me specifically something I can do better? And it doesn’t work in the hallway; it’s got to be in a safe container, some sort of feedback mechanism meeting, um or simply saying, “Look guys, I don’t know the answer. I need your points of view.” And one by one they’ll start, you know, “Where are my blind spots?” Like, I have to set the tone.

Speaker: Simon Sinek: But just be aware that the hierarchy does factor in to someone’s feeling of willingness; it doesn’t mean you have a weak culture. But if you have no challenge in here, that’s a problem.

Speaker: Taro Rabu: Got it.

Speaker: Taro Rabu: And so tell me a little bit of your perspective on approaches to break that sense of hierarchy. For example, we have one-on-one skip levels, etc. “Hey Josh, come up here,” the ET will come up here, whatever. Um, but is there a different thing that we should be doing to sort of invite that level of candor?

Speaker: Simon Sinek: So you can’t break it; you can mitigate it, right? So, uh, if Steven Spielberg walked into the room, you would show him incredible respect. Why? Because it’s Steven Spielberg! Or, in my world, George Lucas, right?

Speaker: Taro Rabu: Got it, like—love it!

Speaker: Simon Sinek: You know, so, so like I’d be like, “Oh my god, it’s George Lucas! Oh my god, it’s George Lucas!” And he says, “Tell me what I did wrong.” I’m like, “Oh, it’s amazing! Right? Like, I love your stuff, I love you, I love everything you’ve done!” Right?

Speaker: Simon Sinek: He can’t break it but he can make me feel a little safer and he can mitigate it. What’s more important for Josh or any senior leader, what’s more important is that they create a culture of challenge from their circles of influence—from the regular impact they have.

Speaker: Simon Sinek: So if Josh creates a challenge culture in his direct reports, guess how they’ll lead their direct reports and guess how they’ll lead their direct reports? Yeah, and so the most important thing is the culture you create in your sphere and then it ripples. By the way, it goes the opposite as well—no challenge in your culture at the top, you’re gonna find only small pockets of it throughout the company.

Speaker: Simon Sinek: Got it! And we call those rebels!

Speaker: Taro Rabu: We call those rebels. We or those, the people who have this weird, like, “I don’t care if you fire me.” You know?

Speaker: Taro Rabu: Totally, totally!

Speaker: Simon Sinek: Right? I love it, I love it. I appreciate that a lot. I want to do a quick time check. Sweet. Good. So I’m gonna shift to a lightning round unless I miss something significant; and if I did, I apologize profusely to you all in advance. Um, alright, um, what three characteristics make a great leader?

Speaker: Simon Sinek: This question comes up a lot, and you know you read articles and they’re like, “Charisma!” You know, I’ve known a lot of great leaders who wouldn’t even know they’re the leader—they like walk with their shoulder against the wall, right? So, you know, those things I’ve seen yes and no. But the few things that I’ve seen universally about amongst the great leaders I’ve met, number one, um, and these things number one and number two sort of go together—number one is courage. Number one is courage.

Speaker: Simon Sinek: Uh, the courage to speak truth to power, the courage to be honest about my own failings, my own capabilities—um, the courage to be open about my failings and my capabilities. Like these things are excruciating— the courage to tell somebody something that you know is going to hurt their feelings. Like, these things—leadership is an incredibly difficult thing to do.

Speaker: Simon Sinek: And then courage, which then begs the question, “Where does courage come from?” And I do not believe for one minute that courage is a deep internal fortitude where you dig down deep and find the courage. Courage for me is social. Yeah. So like I have the courage to jump out of a plane because the parachute on my back gave me the courage and so you need at least one person in your life, professionally or personally to say, “I believe in you. You got this.” And if everything goes south, I’ll still be there with you; that’ll give you courage.

Speaker: Simon Sinek: Number two closely tied is integrity, which is to do the right thing and weirdly we all know what the right thing is, rather than doing the expedient thing. Like, I can’t stand it when companies do unethical things and all the CEOs are dragged in front of Congress and they all say this same thing, “We broke no laws.” No, you didn’t break a law by raising the price of your essential drug by a thousand percent—but it’s pretty unethical. Yeah?

Speaker: Simon Sinek: Right, like we all know what right is and the law is a lower standard. And so the courage to have integrity—and integrity driving my courage—like those things go together.

Speaker: Simon Sinek: And the third one I’d say, um, they’re a student of communication. It’s a huge part of leadership; it’s the skill of listening and the skill of speaking in a way that allows people to not only feel listened to but allows people to feel heard and speaking in a way that people can hear as opposed to triggering people, etc., etc.

Speaker: Taro Rabu: Got it. I love that! Appreciate those responses. I got another one for you.

Alright, if you need this group of leaders, not managers, um, to do one thing this week to help them begin building trust in their teams, what would that be?

Speaker: Simon Sinek: Um, the first thing would be to go back to your teams and say, “One of the things that I love about this company is that the company wants us to be better leaders, better leaders of people, and we had our first gathering that was all about challenging, and that there’s an expectation at some point that we’re going to challenge you to think bigger, think better, do you know, push your boundaries. But that starts with me, and I’ve been challenged by the company to take myself on and be a better leader over the next few months. You’re going to see me experimenting with techniques and strategies. Some of them will work, some of them won’t. Some of them I’ll be good at, and some of them I will fumble and stumble. Be patient with me and give me lots of feedback because I really want to be the best leader I can be for you.”

Speaker: Simon Sinek: So make an announcement of the journey that you’re on because it is a bumpy road—and you want your people to be patient and supportive as you’re on your journey to be a better leader, which in turn benefits them.

Speaker: Taro Rabu: Amazing! Something about that response resonated with me and this is the aspect of there is this return of psychological safety that comes back to us as leaders when we provide it to our teams. And I’m wondering if I’m reading that right; given what you described.

Speaker: Simon Sinek: Yes, it is a relationship.

Speaker: Simon Sinek: Yeah, yeah. And we call you leader not because you have rank or authority—we’ve already established that, right? We call you leader because you went first, first towards the danger, first to speak of your mistakes, first to admit you don’t know. And that courage to go first is why we give you all of the perks we give you: higher salary, and all the other advantages you get as a leader.

Speaker: Simon Sinek: But those perks are not free; there’s a deep-seated psychological expectation. The only advantage you get in a leadership position comes at the cost of you being vulnerable first and protecting the group.

Speaker: Taro Rabu: Amazing, thank you. Thank you.

Speaker: Taro Rabu: Um, alright slight twist here now—what’s the one piece of common leadership advice that you think is flawed that you want to warn us about? Don’t do it!

Speaker: Simon Sinek: Well, that’s a great question. Um, I think the uh, a lot of the old sort of Jack Welch things we hear, you know, do as I say, not as I do—false, totally false. Um, “Because I said so”—false. Give people context for the decisions you make or the questions you ask, even the instructions you give: “Can you do this?” Here’s why. Context is everything.

Speaker: Simon Sinek: Um, and I think—and this one I know is difficult for a public company—but, um, uh shareholders do not come first ever. At best, they come third after your employees and your customers! And if your employees or customers are taken care of, your shareholders will be taken care of. But if you prioritize your shareholders you might hurt your customer or your employee.

Speaker: Simon Sinek: So I think that that old-fashioned dinosaur thought—you can be performance-driven, but it’s for the benefit of the customer and the employee.

Speaker: Taro Rabu: Yeah, yeah—and I imagine that spurs engagement as a side effect.

Speaker: Simon Sinek: And by the way, in this modern day and age where we’ve sort of accepted that shareholder supremacy is the thing to announce and publicly say, “No, it’s a recent thing; it’s a kind of 1980s, 90s thing; it’s not the thing—it’s a thing that hasn’t served our nation, or the companies, or the economy, or the people who work in those companies. Um, it’s only served one group—the external group that doesn’t actually care about us.” Um, and we talked about courage; the CEOs who say, “Invest in us, or don’t invest in us.” You know, “We will not be fair-weather fans, but if you believe in our cause and you like our management, you like our strategy—welcome!”

Speaker: Taro Rabu: Alright, I’m gonna wrap this up with my last question.

Speaker: Simon Sinek: Um, and so what is the one thing you wish? But before I do that, thank you for that response, Simon; it was great. I appreciated it, and I imagine others did too.

Speaker: Simon Sinek: Um, so what is the one thing you wish you knew about leadership when you were at the very start of your journey of becoming one?

Speaker: Simon Sinek: Oh, super simple. Um, I don’t have to know all the answers and I don’t have to pretend that I do. As a young leader, I thought my credibility came from my intelligence. I thought my credibility came from having answers to every question. I thought my credibility came from knowing what to do. Complete nonsense. The single best thing I ever learned that transformed me as a leader, and as a person, is the confidence to say I don’t know.

Speaker: Taro Rabu: Amazing!

Speaker: Simon Sinek: Well leaning on the very gracious Andrea, she has given me the cue that it’s time to open for Q&A! Right? Yeah, we’re going to take a couple of questions. We can start with the audience and then if you’re virtual, drop your question in the MC, and I’ll read it aloud for you. We just have time for a few.

Speaker: Audience Member: Hello! Um, hi Simon. Hi T. Just a round of applause because this conversation was really inspiring. So thank you.

Speaker: Audience Member: I will make this quick. How can we encourage leadership from both different orgs or tribes? Because we’re all around 150 here.

Speaker: Audience Member: Breaking down the perceived gap of alpha between disciplines—P the perceived gap of what, between disciplines? So creative, engineering, product, marketing?

Speaker: Simon Sinek: Oh, yeah, yeah—well, first of all, one of the ways we organize companies is as you’ve said, right? And um, there are a few techniques, some of them more formal, some of them less formal. More formal, which is create teams based on a project with a blend of them and put them in a room together and they have no choice but to work together. I love that. Um, that’s more formal. Less formal is the Kaizen technique from the Toyota Way, which is um, take somebody out of engineering and have them go work in marketing to help solve a problem and vice versa. And they bring all of that; they start to learn not just to present their ideas, but they learn the challenges the other group has.

Speaker: Simon Sinek: Um, and the most important one is get people to talk! Like, you know, for a formal monthly or quarterly meeting where the different groups present to each other, one of my favorite companies that does this really, really well is 3M. Uh, in Minneapolis. And 3M is one of the most innovative that ever existed on the planet. The number of patents they have is extraordinary. And one of the ways that they do it is on a regular basis—it’s not required, but it is very heavily attended—the engineers all stand on the stage and say what they’re working on and say what’s working and what’s not working.

Speaker: Simon Sinek: They don’t believe in failure; they believe you just—whatever you’re doing didn’t fulfill the brief. So I’m trying to make a strong adhesive; I made a weak adhesive. And what they get is the support from each other. So I think a form where people can say “here’s what we’re working on, and here’s what’s not working, and here’s what we’re struggling with,” and everybody can hear what’s going on. I just love things like that.

Speaker: Taro Rabu: Thanks for the question and thanks for the response, Simon!

Speaker: Taro Rabu: I’m gonna read um one from the MC. This question is from Alejandro. How do you break the bias of sharing an unpopular opinion when the majority is leaning to one opinion?

Speaker: Simon Sinek: Um, okay! Great question! Number one, um you have to disconnect, connect, uh, uh the opinion you have from yourself. Meaning it’s not personal. And one of the things that happens that makes things go sideways is when we have a clarity or we have a different point of view, we take it really personally. Right? We want the company to do this; we want the group to do this; we want to be heard. And if they don’t we get upset! And like “Why? I’m just trying to help!”

Speaker: Simon Sinek: Right? But the point is you made it personal, and what I’ve learned is when you shift accountability. Because when you make it personal you take on all the accountability, right? But when you shift the accountability, you’re more likely to be heard saying “If it’s so completely sort of like, ‘Hey, I have a different point of view. I don’t know if it’s right or wrong, but it’s challenging—can I let me just make a point?’” Right? And you say that point and you get pushback, right? And instead of defending the idea and trying to be right versus the pushback—because now it’s becoming personal, right? You’re defending “my idea”—right? You simply say, “Hey, look, look, look, look! I’m not going to fight. I’m not trying to be right. I’m not trying to tell you you’re wrong. I’m literally not going to fight with you. This is your decision; you do what you think is right! I want you to have the benefit of another point of view. But if you think it’s the wrong point of view, then ignore me.”

Speaker: Simon Sinek: And I’ve learned that the more you can emotionally disconnect yourself from the advice you’re giving, weirdly the more often it’s heard.

Speaker: Taro Rabu: Love that!

Speaker: Simon Sinek: Um, any more from the audience in person? We’ve got some time; we’re a little ahead of schedule.

Speaker: Nicole: Sure! Hi, I’m Nicole, I lead our DEI team at Etsy. And my question is, does all of this advice extend just as well, um, from the work context to the personal? Or here we are in a pre-election season—political contexts that come into these conversations come into the workplace.

Speaker: Simon Sinek: Uh, the simple answer is yes. Uh, human beings are engaged in relationship—whether they’re personal relationships or professional relationships, it’s relationship. And many of the same things—not all, but many of the same things—apply. Um, rational versus emotional.

Speaker: Simon Sinek: Are you good at assessing when somebody’s presenting an opinion or something emotional? And it happens all the time. We do it in our relationships—in our personal relationships, right? Somebody says to you, “Uh, you know, you didn’t do that thing three times”—you’re like, “I didn’t do that thing twice!” Like we correct the facts when they’re emotional; don’t do that.

Speaker: Simon Sinek: Right? It’s got nothing to—or we have a rule in company, “If it’s above a five, it’s about something else!” Right? So like at home, it’s like, “Why do you always leave the fridge open?” If that’s the reaction to leaving the fridge open, it’s not about the fridge, right?

Speaker: Simon Sinek: So to be a student of like assessing—like, is this the thing, or is this something else? Don’t don’t be rational in a—you can’t bring facts to an emotional gunfight. You know, you have to— all you have to do when there’s emotion is allow someone to feel heard. And um, and when politics come in—which you know is so uncomfortable and destructive inside—uh, well, inside everything, um, our goal is not to fight with the person or prove them wrong. Our goal is simply to hold space and make them feel heard.

Speaker: Simon Sinek: And that’s a skill that we have to do better at as employees, as brothers, as sisters, as spouses, as boyfriends, as girlfriends, and uh, as Americans, we are crap at listening.

Speaker: Simon Sinek: And if you want to teach one skill in your company that will have ripples that will benefit society and people’s homes beyond, beyond, beyond—start teaching effective listening!

Speaker: Taro Rabu: Nicole’s taking notes back there.

Speaker: Taro Rabu: Okay, we have uh one more question in the MC that I’ll read. This is from Sali. Should the leadership principles or guidelines change based on the changes in the company culture? For example, if a company is getting more performance-focused during a difficult economic time—why or why not? And if the answer is yes, how?

Speaker: Simon Sinek: Great question! Absolutely! Leadership styles adapt for the situation you’re in, right? So, um, there are some leaders who lead with command and control. Command and control is not useless; it’s just not sustainable. And so if you’re always like that, you’ll exhaust your people and burn them out and probably break, um, levels of trust at some point.

But in periods of extremely high stress—like COVID and going into lockdown and all of that—extreme, extremely high stress, it is totally okay for a leader to go into command and control. But you have to have been that, uh, really effective sort of kind of leader that we were talking about to build trust, before that command and control doesn’t work if you don’t have the trust of the people.

Speaker: Simon Sinek: And so if you—I learned this from The Ring core—I forgive the analogy, but you know when you go into combat, leaders just bark orders—that’s what they do. But what people don’t see is that’s not what it’s like back at home station; they’ve built trust over months, if not years, so that their people trust them when they go into command and control. And by the way, be open about it.

When we went into lockdown, when we went into COVID, I said out loud to our company, “Hey, listen, the stress is high and the pressure is extreme and I want to know your feelings; I care about those things. And if I said something in an awkward way in a meeting and our traditional way of doing it is you sort of bring it to my attention quickly, I need you to know, bring it to me in two weeks! I like right now we’re focused.” And people were fine with it!

But I set expectations that it was going to be different and it was going to be short-term. That’s really important! So yes, you can adjust your style for the situation you’re in; what you can’t do is be mushy-mushy and you know, super patient when stress and deadlines are extreme.

Speaker: Taro Rabu: Oh, we’ve got another question here in the audience!

Speaker: Audience Member: Um, so you talked about self-awareness and how that’s like one of the most difficult things to do. And you also talked about kind of people think of psychological safety sometimes as being like positive, and you can have this problem where you have, uh, what I might call toxic positivity. Um, and so I’m wondering how do we measure as an organization whether we’re making progress on psychological safety when we think we’re already good at it and see the problems when the culture is overly positive?

Speaker: Simon Sinek: Yeah, so you’re such a great question. Toxic positivity is thinking everything’s good or telling everybody everything’s good. You know, it’s so—I guess the equivalent of giving everybody a trophy, right? And it’s the unwillingness to ever give difficult feedback.

Now, the question is, have you learned the technique to give difficult feedback so that people will hear it rather than be defensive and angry? Um, uh, and so one of the ways you can judge is is it excessively positive or are you actually creating psychological safety is ask the people on a regular basis, “You know, do you feel safe to admit a mistake? Do you feel safe to ask for help? Do you feel safe to say I don’t know?” and see what people say, right?

Speaker: Simon Sinek: At the same time, you’ll see it in the product—if you have psychological safety, you’ll generally see the number of people quitting go down; you’ll generally see innovation go up; you’ll generally see more consistent performance—but you’ll see it also, just as the leader of the group is, you’ll see your team teaming together, you’ll see your team relying on each other.

Speaker: Simon Sinek: Uh, and the more that you step back—like, I made an executive sort of decision the other day and I was sort of a little not very clear about what the decision was. You know, I was like, “We need to do this!” Right? Not telling anybody to do anything! And somebody said, “Well, what’s the decision?” And I said, “I want each of the team leaders to go back, do experiments with their team, and then tell me which is the best solution.”

Speaker: Simon Sinek: And so the more you push out the opportunity to try and experiment, you’ll get the benefit of all of that and you’ll have a sense of it. But there are multiple data points that you’ll need, some of them formal, some of them informal.

Speaker: Taro Rabu: One quick follow-up, so if there’s no psychological safety, how are you going to get people to tell you that there is the space to tell you that they made mistakes? Is it just like looking at people doing that? How do you know how much is enough versus...

Speaker: Simon Sinek: Yeah, so one of them is accountability, right? So is somebody checking in with you every time before they make a decision? “Hey, hey, is it okay if I change this from blue to green? Hey, is it okay if I call one of our people? Hey, is it okay if I send this out?” “Hey, is it okay?” Okay, give the support to your boss, right? The problem is, is the more we answer all those questions, we’re actually removing accountability from them.

Speaker: Simon Sinek: For me, one of my biggest pet peeves is when we go on a company off-site or vacation, that we’re on our emails and checking in on everything. Nothing undermines trust more than you can’t even go away for a week and you don’t even trust your team to make decisions while you’re not there. You know, like when I go on vacation I tell my team, “Hey, I’m gone for a week. If there’s an emergency, deal with it—I’ll see you in a week. Bye!” Right?

And what that does is it says “I trust you and you’re accountable, not me.” The more I answer their questions, the more I remove accountability from them. The more I—and by the way, accountability means sometimes they get it right and sometimes they screw it up.

Speaker: Simon Sinek: And so when they get it wrong, is it stylistic? I just would have done it differently. We have to sort of learn to put our egos aside there, but if it went sideways—assuming there’s no negligence, you know—like, there wasn’t gross irresponsibility, that’s a different conversation. But if something just went sideways, you go, “Oh my god, that went sideways—okay, let’s figure this out. What’s your first suggestion? How can we put this right?”

Speaker: Simon Sinek: I got you! Let’s just figure this out together. And the more of that, that happens, the pushing accountability—we’re not very good at. We’re not very good, because we’re constantly connected, which accidentally removes accountability for people.

Speaker: Taro Rabu: One is this on?

Speaker: Simon Sinek: Okay! Thanks everyone for the questions! I have the pleasure of wrapping us up. And so it’s my turn to be nervous now, too. I’m just kidding!

Speaker: Taro Rabu: Um, I just want to say thank you to T and thank you to Simon; I think they did an amazing job. Let’s give them a round of applause!

This article was originally published on https://craftengineer.com/. It was written by a human and polished using grammar tools for clarity.

Follow me on X (Formally, Twitter) or Bluesky.