CEO

“A CEO can't stay connected with every person in an organization, and so they're really, they should be that, you know, a confidant to the CEO, but also the person who can roll up themes and issues that need, need to be addressed in an organization.”

“So when I talk to our founders, I always talk to them about you know, the true, the worth of HR is, is that they are an extension of the founder in their vision, in the way that they want to build the company, in how they bring people on board, and how they ac…”

“I always start a conversation with a CEO asking, is the employee going to be surprised? And when the answer is yes, it means that there's been no feedback.”

“And we find that the team, you know, generally works better if the product innovator is the CEO of the company.”

“I think if it's something that goes in direct relationship to the core of the company something like GM you would want to see the CEO out there apologizing and owning that and making sure that, that CEO is communicating what they're going to do differently. So…”

“I think I would, quote unquote, save the CEO for when you actually know the facts and you know the plan versus have the CEO the day to day, like, look, we're still looking into it. You know, that's just a waste of time because that person is also going to be v…”

“The other thing I've found that works incredibly well, and maybe they're just indulging me on it, but I have found that it works well is that I just, again, in my later discipline years, I'm trying to get better at this, is Is to just keep, instead of having, …”

“Cause the CEO is much more likely to open up to someone not on their board for sure.”

“In the audit committee, when you see something not going well, it isn't really a CEO thing. It's a company thing. So, so you're not, You know, when you're doing the readout, you're just saying, we see this problem at the company. You're not saying the CEO is m…”

“The target hack has probably had the single biggest effect where the CEO got fired, and, you know, and this is one of those things, like, you know, this is fresh in mind, because I'm thinking about how to deal with kids, but, like, if you're dealing with CEOs,…”

“A monthly letter from the CEO is very helpful. Both for, more, equally for you as the CEO, because it forces you, I think Spencer may have said, or Aaron may have said, but, you know, forces you to put your thoughts together in a, you know, cohesive way.”

“One of the things I use to judge the capabilities of the CEO is, can they get their shit together and get the board package out in some reasonable amount of time, two to three days in advance? If you get it the night before, and if you can't manage getting the…”

“I always kind of had a rule of thumb, like every time a VC joined my board, I'd add a CEO.”

“Since all those issues are performance related, it's really awkward to have one of the CEOs direct reports in the room. And you find a lot of board structures that start off with a CEO and a technical founder or whatever, a co-founder. Get them off. Get them o…”

“What we see is that, that, like earlier, I was talking about the CEO board level and then CIO chief security officer, We see that the CIOs and the chief security officers, they understand that, that they've likely been breached and they're very into monitoring…”

“One of the things that we've seen, it's the people that are chief security officers, or security professionals, or even CIOs, their level of vigilance and their level of concern about this over the last 18 months is pretty consistent. What's clearly changed is…”

“One of the things that turns great candidates off very quickly is if they feel like the company they're talking to or the CEO they're talking to really doesn't know what they want in a particular role.”

“For an executive search, CEO of founder being really the first point of contact with the company. So that the executive has an opportunity to start developing that personal rapport and relationship with the CEO right out of the gate. And if you're able to star…”

“I ask these CEOs that I meet with all the time, who's in charge of making sure that that happens? And they don't know. There's not, there's nobody in the organization they can point to for accountability on that score.”

“For the people inside their company, they're the VC. They're the source of funding and political capital that everybody needs to sustain what they do.”

“And it's like we've trained ourselves to stay the fuck away from that place, but I go straight where it hurts the most, and I talk about that. And it never fails. All these CEOs, they're very, very successful, they're running public companies, they look in the…”

“The combined board will never know more than you can balance on a pin hat of the company, and they shouldn't. That's for the CEO to know.”

“The need may not be there, but I think CEOs might be being pretty short-sighted that there's not going to be competition down the line, particularly as they try to expand inside a account.”

“The most important thing is you have to, you want to control the communication that's going out to your entire workforce, which means one person needs to stand up and communicate to everyone what's going on that day, why it's taking place, and that you as a CE…”

“If we're just talking pure compensation, then I think cash is actually a better vehicle than stock, because one, like, stock is variant, and you may not get paid not because you can't invest, but because the thing goes to zero. And is that really your fault as…”

“Maybe not at the very early stage, but if you're a successful company, and we should all plan for that, you're not going to get great talent Unless they have direct access to the CEO.”

“The truth of this kind of decision is, you know, you make this one all alone because you're the only one in the position to synthesize the knowledge. And so if you ask somebody, should I take like a crazy risk and decommit everything I've committed to this poi…”

“Being a board member makes me a better CEO.”

“I usually counsel CEOs what, before they go out, have something in your back pocket. We had two or three initiatives that we tested at small scale that we knew were going to work and add to the business.”

“CEOs only listen to leading indicators of good news, never leading indicators of bad news, only lagging indicators of bad news.”

“And what most CEOs do is they never actually kind of fully articulate out the updated strategy. So a very important discipline is to at least once a quarter just take whatever your old strategy is and re-articulate it with all the new things that you've added …”

“As soon as you think about go-to-market, right, and you start to think, okay, now I'm going to spend marketing dollars. Do I understand what my lead generation costs? Now I'm going to hire sales. What's the throughput and conversion rate and quota and all that…”

“What happens with most finance people is they back down at that point because they're like, well, fuck, he does know more than I do, even if he's wrong. Whereas going, okay, like, let's just draw out, like, here's all the things you want to do. Like, this is w…”

“In a product-centered company, the VP of product and the CEO, like, no matter how they got formed, they're co-founders.”

“I spent essentially five hours before I even agreed to interview at Square with our CEO, just getting to know him and understanding what his vision is for the company, what he cares about, what he doesn't, what his philosophy is, how he works, because you can …”

“I think the NPS is the company's core, it's the CEO's core, not the CCO's core.”

“I think people are realizing that customer success needs to report directly to the CEO.”

“The CEO is seldom the smartest person in the room, but she usually has the best judgment.”

“There's a difference when there are five of you, or eight of you, or 10 of you, when there's 500 of you, or thousand of you, and the person's job who changes the most in a growing environment is the CEO's job.”

“Because when you're up to about a 125 people, you, the CEO, You're the leader of the company. You can know everybody. When you got 500 people, everybody knows you, and you know a very small part of the company.”

“If you're a hundred people, there's two to three layers between the CEO and every other person.”

“When a CEO refuses to do that, the Caliber of talent they can get just drops 10 notches.”

“This is why I love having agencies do media training too, because agencies can really tell a CEO, actually, you look like a complete dweeb, or this message completely did not resonate, where the employee sometimes has a harder time landing that message.”

“Often the boards are not controlled by the venture capitalists, but controlled by the CEO and, you know, kind of, you know, other common shareholders, in which case the board really can't, you know, the venture capitalists can't unilaterally do anything. They …”

“And we like to talk about the price because, of course, it's a lot more fun and sexy to talk about money, but it's, I think, you know, managers and CEOs make their reputations, quite frankly, in these types of situations where, you know, they are thinking firs…”

“What's most important is that open source has a project leader to drive the effort, and typically that project leader becomes the CEO of companies.”

“But the disengaged, the person you like, who's kind of just disengaged, and kind of just phoning it in, is the hardest one. So, I think you have to do a hard thing about hard things, and there, I think there's really no option but to have the conversation, and…”

“And the actual truth, when you fire somebody, is mistakes were made. If you're being objective, it's always partially your fault, usually more than half your fault, if you're honest.”

“It's when you're asking other people, what do you think? Or when you're starting to have the thoughts of like, is this the right person or is it not the right person? You're done.”

“If you have somebody who's really doing the job, what you always find as CEO is they're kind of teaching you about how the function should expand, how should it grow, and if you're giving them a lot of ideas, like more ideas than you're getting out, then that'…”

“There's like all this lore and kind of stories get told, and so it's like, okay we're gonna do a layoff. We need to cut costs and we knew that we overhired, and we got sloppy shit all over the place. And so we're gonna do a layoff, and like, we don't want to d…”

“If you incentivize, if you pay the CEO based on earnings per share and particularly quarterly earnings per share, which I think we did at HP or at least annually. You know, if you optimize for that, you can do things that would undermine long-term productivity”

“If you don't even know how to build a plane, if you have no idea, if you've never done it, if you've not even been in those meetings, then the decisions you make as CEO are very likely to be not only wrong, but potentially dangerous.”

“Which is also why I think that for CEOs, you can't do consensus hiring because you end up with lack of weakness.”

“In the companies, and you can literally measure from the CEO, how many levels do you have to go to where they really know software? Those companies are, you take a Tesla in this example, Elon knows software. So you're right at the CEO level and therefore the p…”

“Where basically I see CEOs fail all the time, is in that hesitation between, ok, I see it, but I can't act on it because there's just too much scary stuff between me and that.”

“Unless you learn how to be A great employee, like some way, somehow, it's hard to be a great CEO.”

“A CEO cannot get a reporter fired, but a reporter can very much get a CEO fired.”

“Generally, like you, if you're a CEO, and you don't fly low and fast, It's going to be a mess because you don't, you never get the truth because the truth never makes it to you, like through your people.”

“Don't try and fix them. They can't be fixed. It's not going to happen.”

“He's paranoid enough that he knew that that could be an issue, and then he trusted himself enough to go get deep enough to decide whether to do it or not, as opposed to, you know, ignore it. Like these guys are trying to kill me. I don't want to see it. Which …”

“I've yet to find the CEO who wakes up in the morning and wants to run a smaller company. He wants more employees and he wants more profit.”

“I will say the best CEOs and the worst CEOs have something very deep in common. You know what that is? The organization can run without them.”

“I sit in these boards too. So the board goes to the CEO. What does the board say? We need more AI. And what does the CEO said? Oh, okay. I'll get like a consultant to do more AI. And then they have some centralized project that nobody knows how it works. They …”

“And a lot of CEOs in those days, and by the way, still, they rank their success in, in, in doing an interview or giving a speech based on minimum, minimum controversy, right? So they come off stage. I, I've worked with lots of CEOs. Like, they come off stage. …”

“Is, is AI going to be able to do this job, like even the CEO job or jobs where the leadership is? And the answer honestly is probably yes. Like in 2035 with a rate of improvement, it will be able to do so.”