Managing Up

"The underlying dynamic that must be true in any organization on a fundamental basis is you can't make your boss look dumb because if you do, they're the person who decides, 'Oh, this person's not performing,' or whatever. And that one little asymmetry, that one little fact... is what leads to the systemic compounding thing where you get these really weird dysfunctional emergent things that everybody hates."

"With Max, I also wrote a parallel document of hot takes. So once a quarter or so for the first year, I'd write a document that was just like, hey, for sake of provocation, if we wanted to fundamentally change a few things, here's ideas on what we could fundamentally change."

"As having a founder that can effectively operate in founder mode means that I can go and have a conversation with the CEO and say, "Hey, look, we have this huge opportunity and these are the things that aren't working, and I need your help to help figure out how we can move the needle more substantially in the direction that we need to go.""

"A lot of times I think there is a big disconnect between an IC focusing on their discrete area and try to optimize for local maxima, versus understanding, okay, my manager's thinking about these things and this is how I fit in, and understanding maybe they have a gap to understanding why your area is important."

"The advice I find I have to give more frequently than any other in my career, as a manager, a board member, an advisor and a friend, is for people to more directly leverage their leaders."

"We actually used to have a format for that we called HPMs. Highlight, people, me. And every manager at Facebook from like 2008 to like 2014 would send to their manager, or even their leadership group."

"Mark's voracious for all information and all points of view... you'll give him feedback, he listens... over the course of the next week or two, you'll just see shifts."

"I probably credit Sheryl Sandberg for really changing the way I approach new jobs... She pulled me into a room and gave me talking to."

"I find that in general people just way under communicate upward inside of companies. And then they'll complain that executives are out of touch when they aren't telling executives what the executives need to know."

"One of the ways I try to frame it to my team is if you're not an executive, whatever you're working on, you're basically writing and telling a story. And when you talk to an exec about that story, you have to start with chapter one, which is what part of the company strategy are you working on? What metrics are you trying to improve? What assumptions are you making that are guiding what you're building?"

"Something I commonly say is that executive communication is actually executives communication. You're communicating with individual executives that all have different styles and different concerns about the business or about the particular problem you're working on."

"The most powerful way I have found to get trust with many people is to have them accountable for an outcome of mine, which is to know. So if I wanted to accelerate trust with Lenny, I will ask Lenny to teach me."

"Brian assumed everybody else was going to work at the same pace and duration... His point of view is like, 'Hey, we're having a meeting in the office tonight at 10 o'clock. Be there.'"

"I was mentoring Brian on leadership, but he was also my boss... It required me to have a certain amount of humility as well as to be reporting to a guy 21 years younger than me, Brian."

"I would say, 'Lenny, let's do a little pep talk, you and me before the meeting.' I want you to start the meeting with the following as you present and Brian's in the room. 'Brian, let's talk about what we're trying to accomplish here. Let's get really clear... on what both, what's the intention of this iteration that we're doing on the product? What defines success, and what do I want to get accomplished in this meeting?'"

"I always wanted to really limit the deck as much as possible, because I didn't know where the meeting was going to go. I wanted the decks helpful at the start, at the very start, to just set principles, set goals."

"I think I was just willing to take some risks and really push for the things that I believed made sense even though maybe based on the titles that I had at the time, I wasn't sort of inherently given a seat at the table and really pushed my away into some of these conversations and then was eventually invited to them."

"we ran into the COO at the time and out of the blue I think he had asked us what we thought about pricing and packaging... we ended up kind of pitching in the midst of pints being sort of handed every which way you could turn this vision for a completely different way we might approach pricing and packaging, and he was pretty intrigued and he said, 'Why don't you come to the next executive meeting and pitch us on it?'"

"I sat for about a half a day and I thought, I think I can help here, drew out an org chart, put my name on the top, walked into my boss's office and said, 'This is one potential solve of your marketing organization question, is we'll bring product and marketing growth together. I can be in this position. Here's how I'd change the management structure underneath this.'"

"Management can be a lonely job, because you feel like you're responsible for everything. So having an ally, it's just a huge weight off people's shoulders. And I think a lot about social engineering. The social engineering's here is just the simple, 'You help me, I'll help you.'"

"I call this going two stack levels up, two stack levels down in terms of your curiosity and what you understand... you should understand your boss's priorities and your boss's boss's priorities. Eventually, that means you have to know what the board is thinking."

"If you come with data, if you run a secret experiment and you come back and you show them you usually get one of two results. Either they get extremely mad at you... But the more common case is they're pleasantly surprised and that's what happened with Steve Jobs, as well."

"After a little bit of that, I was like, 'It might be easier if I just go, I might be able save you some time and some energy if I just joined you.' And it was a way that I took myself into this higher level meeting, framing it as something that was going to help out my boss. And it did. It wasn't dishonest, but it was a pretty effective way of advocating to get into this meeting."

"It shifted the pushback of like, 'We can't build this thing, it's too many features, we don't have enough time, we don't have enough resources' to, 'Oh, we all want a really elegant, really smooth, slick experience for our customers. How do we do that? What's a trip design or a new concept that is actually going to elevate things?'... It wasn't about saying no. It was about understanding what we're all actually sharing as a goal which was a great simple customer experience and then actually building that."

"One of the things to ask oneself is what draws me to this position in the first place? How have I been complicit, not responsible in creating the conditions I say I don't want. How have I benefited from the dysfunction that exists in this organization?"

"You have to find a way to work with those [manager's idiosyncrasies]. And I think that adaptability, like I'm just sort of, I like being a moldable puzzle piece where I can just fit in."

"it's understanding the spirit of what they're trying to achieve. Being able to go back with, 'Hey, I understand the spirit. The spirit is that we're trying to get people who previously didn't consider Airbnb before to come and use Airbnb, but the right way to do it is not this very time-intensive, cost-intensive way to inspect all these homes. The way to do it is to be much more granular in what we ask people when they upload their home and more checks in that. And that could be automated and through technology as opposed to through humans.' It's coming back with actual options."

"If you understand your manager's job, which is how to get better outcomes from the team, and also you understand what exactly would your manager consider success for the team, it also makes it easier for you to then be like, 'Oh, well if I do this project, then that clearly seems like it's a very direct path to creating value for the team.'"

"To me, it really is about the relationship with the CEO or with the founders because that's the root of a lot of the issues that come out of that scenario... Imagine that they're terrified all the time, and see if that makes their behavior more clear."

"One key attribute is there's one clear driver of the project, who's effectively a founder... and also there's one clear decision-maker that they go to. That was true back when we started and it is true now. If we need something or have a question about something, I talk to Elon."

"Where the gaps come between that and becoming an executive is interfacing with the board, understanding the financials super deeply so that you can create revenue projections off of what your roadmaps and your product's strategy is going to be."

"You print out your calendar or you show it to them on your screen, and you say, 'Hey boss, I need 10 minutes with you, Monday morning. Is that okay? Can I get 10 minutes with you?' And now, what you're going to do is you're going to show them your time box calendar for your working hours. You're going to say, 'Okay, boss, you see here's my time for email. Here's my time for that meeting you asked me to go to. Here's time for that big project I'm working on. Now, you see this other piece of paper? Okay, you see this other list here? This is a list of things you've asked me to do that I'm having trouble fitting into my calendar.'"

"The first is, I think as much as possible... is getting to the point where you have alignment on the principles for what it means to build a great product of that company. Not just about if the intuition and tasting gut, but how do you distill that to principles that become the language of the company so that everybody else can start thinking through a similar frame or similar lens when you're designing a product."

"I think when to involve the founder CEO in a project is really important. The short version I think that works the best is almost like a U-curve where the X-axis is time and the Y-axis is level of involvement. I think you want to get the founder CEO really involved early on, especially if it's a big new project, to make sure that there's strategic buy-in... Then I think at the very end you want them to really be bought in that did you build something that's up to the quality... of the company?"

"I went to Salar and said, 'Hey, I think I should actually report to Hunter. I think this would work better if we kind of combined the organizations this way and then we divided and conquered this way.' ... no one has ever come to me in my career and said, 'I would like you to layer me in this other person.' But in that moment I was just like, 'This is how I will do better work. This is how I will get better support.'"

"I think CMO is a very, very hard role. And also, I think it's a role that is very hard to do without a lot of trust, and without a deep connection to the founding team. Everything you do in marketing is very visible, and you're kind of touching something that matters so deeply to the founding team."

"I think oftentimes people refrain from giving feedback when they feel like that feedback is going to be intrusive. So just inviting your manager to say, 'Look, I'm really looking to level up. Please give me feedback whenever you see something. You can give it to me in real time. Don't worry about wordsmithing it.'"

"As someone who's working with a manager, there's kind of two things that you're constantly solving for. One is the degree to which you're aligned with your manager, and the second is the degree to which your manager has confidence in you."

"He would tell you what the rules of engagement were for every meeting... He'd be like, 'Look, I'm going to give you a spectrum of A, how much I care about this topic. Everything from I don't care... all the way to I'm the founder, I'm the CEO, just do this.'"

"Making your ambitions known to your manager, to your leader, is a good thing that you should. And so, when the right opportunity comes, at least your leader or manager is aware that, hey, this person wanted to work on something more challenging, so maybe I put her on that project."

"Maybe I should have beat the drum a little harder about just how unlikely it was that we were going to land the kind of distribution in month one that the model sort of required. If I had to go back and do it again, I think I would spend maybe more time investing and illuminating that aspect of the digital universe."

"I take the job full knowing that it's going to be wildly different than Pandora... in the context of Snapchat, at best, I was going to be Evan's right hand, a person that principally executed his vision."

"I think that most people assume that their boss has to manage them and they feel a little bit resentful that, why should I manage my boss? They're getting paid more. They are my manager. They have more responsibility. And you can continue to think that way and your career might be fine, but if you embrace that if you manage your boss, they're going to appreciate you much more, you're going to get more opportunities, you're going to have more trust with them, there's all these great things that happen when you decide to manage up."

"the most senior people are best at managing up. This is why they got promoted in the first place because they were great at managing up to their bosses to understand what was worrying their bosses, what was keeping them up at night so that they could take that off their plate. They're great at keeping their bosses in the loop on what's happening so their bosses, aren't constantly having to ask and pepper them with questions every day"

"proactively giving the right amount of context for your manager to be able to weigh in on what you're doing and to be able to give feedback, I think that's super, super important. And then thinking about the right level of context to give them, is this a reversible decision or is this one that is irreversible or difficult to reverse or expensive to reverse?"

"I sent my manager a state of Lenny email every week, just titled the state of Lenny. And it had basically three sections, my priorities currently, blockers that I need their help with, and maybe that was the first thing that I put up just to make sure that they saw that, and then just things on my mind currently that week."

"When you just ask your manager, 'Hey manager, what should we do?' You're putting a lot of cognitive load on your manager to need to think about the problem, think about potential solutions, craft the solution, and then tell you what to do. Whereas if you instead said, 'Hey manager, here's what I think we should do.'"

"Dylan is very based on intuition and instinct... part of my job is to build out that logic streak for him of how did you arrive at that conclusion so that people can understand that at scale, in a way. But he's very much about that. Or I think there's a way which, sometimes, it's a product manager, you want to lay out a problem and say, okay, we're going to first focus on this problem, and then [inaudible 00:29:21] these three approaches. We're going to take this approach and have a review at every step along the way. But for Dylan, I think, it's very hard for him to really fully get bought into it until he sees the end implementation to viscerally feel if this is a good solution or not."

"I think the more concrete an artifact is or the more you can debate something, the better. I ask for examples a lot, I try to ask follow up questions about things and make sure I fully understand it. And I think where I get stuck sometimes is if I ask follow up questions and we don't have answers yet, and then my response might be, 'Let's go find the answer to these questions and then let's go back to this conversation', if I think it's something that's really important."

"Say you're going to do the thing, say that you're doing the thing, and then say that you did it... it's a great time to reaffirm you're doing or invite the conversation that this is no longer the thing to do."