Leader

“In today's world, you can't be a leader And not be pushing your team. I truly believe like you have to be in the details and the bar is so low. There's no excuse. It's so easy. Like there's no excuse to not set up and build yourself today.”

“Inevitably to be a great leader, you have to be great with people up to a point, and then you have to have that level where you don't care. I don't care if you agree with me. I don't care if you like me. I don't care what you think about me, but I need you to …”

“If we are the leaders of this company, we have to know everything there is to know about how AI works, how you build with AI so that one, we are more effective and two, we're building for where the puck is going.”

“I, there's all, and I think that for most leaders, when we confront failure, we, our first assumption is it's a failure of incompetence, and it rarely is. Most failures at a high level are failures of overconfidence.”

“The more successful you get, the more you forget that, you know, your presence can have negative or positive effects. Like when you give feedback, sometimes you have to be careful at which levels of the game because it can just ruin somebody or simultaneously …”

“From what I've seen, 99% of the time, you know exactly what to do. The number of truly, truly difficult questions that require you to know some sort of advanced theory, or advanced philosophy, or run some huge amount of calculations that are very non straightf…”

“My belief is most leaders want to be better, but they don't know how. You have to give them the tools, the specific things to do to make them better.”

“We normally don't learn all that much when we interview leaders. Just like a great ball player, they don't know what they do.”

“What I tell leaders all the time, Ted, is they need to get out of the feedback business and get in the recommendation and suggestion business. They're going to be able to give a lot more feedback a lot more often with a lot less resistance and defensiveness ju…”

“Most leaders aren't mature enough to do that because they can't stop from them saying and finishing what the observation means.”

“Too many leaders depend too much on telling people and delivering feedback in a more direct way.”

“The other thing I always tell people I've managed is it's your fault if the leaders didn't buy into your idea. Like it's not, you can't just be like, ah, they never, they just don't see it. It's not my fault. They agreed to do something else. I always tell the…”

“When you name the intention very, very clearly for someone, they're much more likely to interpret your behavior through the intention you just named, because your intention isn't to control them or make them feel small. But if that's also something they have a…”

“That's the biggest shortcoming I see of a lot of leaders. They cannot stand not to be popular with the people that are beneath them. They avoid conflict, and which means they avoid making the right decision.”

“There are some wars, you don't need to win. You just need to leave those wars. You have to pick up your fights. What is worth fighting? There are some wars that are not worth fighting at all. Drop them.”

“There are some problems you shouldn't fight against. You should just surrender to those problems. You should become humble in front of those problems. And those problems don't affect you. Right. We want to fight against every problem. We want to solve every pr…”

“Most people surround themselves, especially, you know leaders surround themselves with weak people because they feel that they feel stronger among those weak people without realizing that they are going to become an average of those five.”

“Re-clarifying roles and expectations, re-describing the elephant over and over and over again is one of the hardest parts about being a leader because you feel like a broken record, right? You feel like an idiot. You're like, I've said this 45 times. Turns out…”

“Great leaders know that when you try to advise and have the answer all the time, you're not actually equipping your team to go solve the hard problems. You're training your team to come to you with all of the hard problems. And coaching is a different way. It'…”

“So don't coach and make it a game. Like, you want your person on your team to guess what's in your mind. That's a, not a good time to coach. You have something you absolutely want them to do. You know the right answer. You want them to be motivated to go do it…”

“Now leaders earn respect by voicing uncomfortable truths. It breaks tension. It actually makes people believe in you more than anyone else in the room.”

“I think it's pretty clear that people prefer leaders who are intuitive and who are overconfident. Leaders who deliberate too much are viewed with suspicion, you know.”

“Certainly anything that threatens the leader is not going to be adopted, and leaders may not want something that threatened their subordinates either. People are really very worried about embarrassment.”

“Because someone is going to pay you a million dollars, and at least for next 10 years, that trust can only be built by humans, because you can't jail an AI, but you definitely can jail a person. So a lot of these things which require this human trust, for lack…”

“When an organization achieves advantage, it develops a tendency to continue operating with the same strategy that produced the advantage. It is the leader's main role to keep alive the quest. For advantage.”

“So like my only like good litmus test for that or like red flag is if a leader comes in and they're starting to make a bunch of changes without deeply, deeply, deeply understanding the company or the company's problems and without bringing like real humility, …”

“When I walk into a meeting, I try to remind myself, okay, my mission here is just to add more velocity and to raise the standards. No, nothing that they will present is going to be fine. No, this is the mentality that any leader has to go into, because if you …”

“Your ability to win as a leader is your ability to change the behavior of your teams. Startups win or lose on speed. Can you change and adapt and iterate faster than your competitors and keep ahead of the market?”

“Because you also want to change the culture, maybe. So you need someone who kind of fits in, but not fully. So, so that person or that leader can change the, so there's a lot of discussion around what is now the ideal success profile of that specific leader.”

“I describe a good leader as sort of like a conductor of an orchestra. It's like I can have the best players in the world, but if they're all playing from a different song sheet, it's gonna sound terrible.”

“I would actually encourage leaders to almost model like 1.5 X where they're hoping out of their team. So if you're like, I want my team to move faster than you as a leadership team need to make faster decisions.”

“If you have a founder, you have a leader that has relentless pressure, that's from an internal source that they're applying to themselves, chances are they are also going to apply relentlessly to their team,”

“They're going to follow you for a while because you've got a really great idea, and the minute they've got another choice, man, they are out of there.”

“I think that there are aspects of a sort of ecosystem or a complicated company where you hire great people. And it's not that you get out of their way, but maybe you support them in a way where they feel empowered to do their job really well.”

“The people who fail are people who try to do too many things too fast.”

“I think the reason that most leaders do not quote unquote amp it up is either because they settle into and get comfortable with a lower than exceptional standard that just becomes the norm for them, so they don't spot what exceptional performance looks like, o…”

“I think we have a problem in this kind of like self-help, personal development world where I think a lot of Let's say like thought leaders and leadership and all, I think they're disconnected from what leaders actually go through.”

“The number one reason most people don't give good coaching is because they've never experienced good coaching themselves. And most people can only give to other people what has been given to them.”

“I think there's a difference between micromanagement, which is like telling people exactly what to do and being in the details, being the details is what every responsible company's board does to the CEO. It doesn't mean the board is telling them what to do, b…”

“And then all of a sudden you, as someone who holds power within your organization, are starting to impact the psychological safety of those around you, because you're not really talking about what's going on.”

“As the leader, like, you're a symbol in a way, right? You can't go in a town hall in the whole company and say, listen, guys, I'm actually getting severely depressed at doing the work, or like, you know, I'm suffering from burnout, and I'm not sure I can go th…”

“People will actually trust you more. If you show vulnerability. If you say, hey, this is an area I'm bad at as a leader. This is an area I'm good at. Because that helped build a relationship with people.”

“It's easy as a leader to think out loud from time to time without noticing that people really listen to you when you think out loud, and oftentimes they'll go off and do things because they think it's what you want when all you were doing is wondering about so…”

“The truth of it is they're not going to be. Most of the time. But can they hit a bar that is 80% of what your expectation might be? And is that going to be enough? And I think for some people, they're just still going to carry that frustration, and for other p…”

“And, you know, I think people too often put limits on what they think their people are capable of out of fear of overstretching them in some way.”

“This is what naturally happens to human beings. It's just, it's innate. We slow down to a glacial pace unless there are People who are going to drive tempo and pace and intensity and urgency. That's what leaders need to do because people naturally slow down.”

“What you do need is to listen to contradictory feedback. So what was the premise here is you're being told that something that you hold as your strength is actually in your way or a development area. Do not dismiss that. Recognize most likely you're doing it c…”

“Leaders want the upside of innovation, but they're not really willing to deal with the cost of innovation, which is like, look, if you're going to swing big, you will invariably stumble sometimes.”

“There's a really healthy amount of avoidance that a leader needs to have to redirect people to solve their own problems instead of allow your team to come to you, ask you what you think about it or how you should solve the problem and deputize them to come bac…”

“I think very few leaders can be the best wartime CEO and the best peacetime CEO. Usually you're one or the other, you're an amazing peacetime or amazing wartime, and then you sort of stay too long when the season shifts.”

“When you fail to remove a poor leader, You hold the rest of the organization hostage, and boy was she right.”

“Whatever the person says, sit there, shut up, listen, take notes, say thank you, don't judge, and don't critique.”

“Feedback on leaders is worse and worse and worse than it's ever been. Behavior of leaders is better and better and better than it's ever been. Leaders today are more effective than any time in history.”

“I think that the traditional interview process for leaders is broken and the best way to learn about someone is really working side by side with them.”

“Somebody who's a loner and somebody that doesn't like to get along with people who has shitty relationships with their family, not as a rule, but it's pretty hard to imagine that they're going to be a great leader.”

“Cause lots of times what happens is leaders, they find out about a change. They think about it for weeks or months. They go through their own arc where they come to see it as doable, rewarding, normal, and then they turn to their folks. And explain the change …”

“There, there's sort of a rule in operating, right? Like you can only vent upwards. Like if you vent down, you can build a lack of trust.”

“And I think part of as you decide that you want to try to help a company grow and be in a leadership position, part of what you're signing up to is absorbing the pressure. That is part of your function. If you just take the pressure and pass down the anxiety, …”

“And a leader who is constantly questioning what their leadership, their own leadership thinks of them is operating at half speed, right?”

“On the other side of the coin, you know, there's a value in sort of mythology sometimes because people started thinking, you know, McChrystal, some kind of Zen warrior who, you know, the stoic who eats one meal a day and he's, Etc. He's never slept, slept in h…”