The Wisdom Wall

“one challenge of the last decade, right, is that resource allocation was largely dodged by many companies because they just Decided to spend more and hire more folks. And so oftentimes, um, the real constraint was, like, hiring velocity on a given team and your ability to kind of, like, get recruiting aligned with your…”

“I think one of the lessons in management over the last decade has been that You know, managers are people leaders in that it is micromanagement that it is bad to get into the details. I think this is like an anti pattern because it creates disengaged and like sort of like context free leadership”

“the most valuable thing as an executive you can do is educate like the other execs on how engineering works, not kind of protecting engineering from visibility from anyone else.”

“Chief architects and CTOs are pretty inefficient in terms of Actually getting enough context in their heads to make a good decision on any given, given point.”

“And then committees, like in almost every architecture group turns into a committee where they have to balance their, their different perspectives, or they're just like slow and kind of inelegant. It's rarely true that a committee gets the best decision.”

“Salespeople are not fungible, replaceable individuals. They're, they're like uniquely talented people.”

“You can be ideologically like pure and say we shouldn't measure something, but all it does is slow down the learning of the organization around you. Doesn't actually help you accomplish your goal.”

“in cases where there is no clear path forward or where the folks who have the context around the path forward are like violently in disagreement, it pays to get into the details and make the decision yourself.”

“Organizations are really, even, like, very kind of large organizations are the culmination of, like, a few individuals judgment, and there's just no way to escape that, even if you have, like, a huge budget trying to.”

“So like almost always when you get these like really like offhand random ideas from executives, there's a kernel of insight there that you can extract by kind of asking more, more detailed questions to them.”

“They can't develop everything you need to be an effective senior engineer in four years working in one company. You need to like see different views on these different problems to really kind of develop mastery.”

“helping managers understand their job is to build conviction, not to kind of take the average of everyone else's conviction. And that they should override their team if they have conviction and they don't think that the concerns that are raised are meaningful.”

“The number one way that I see new engineering leaders struggle when they come to a company is they just assume the context from their previous company applies as is. And if you've got new leaders who come in and really make a mess of things, It's always because they assume the previous context from their earlier…”

“And one challenge at companies is like, you usually don't write down why they make the most important decisions. Like you would Sort of assume it's the opposite. But if you go into a lot of companies, the small decisions are documented, but the really important ones, like, why did we go into this business? Or why are…”

“as an authority figure coming in, it's easy to kind of look at those folks as holdouts, people who are resistance, resistant to change, people who are, you know, just stubborn, but it's usually those folks who have like the most valuable context.”

“there's this like pervasive belief that there's no strategy anywhere, but I've really come to believe that strategies everywhere. It's just like rarely written.”

“if you just write things down, no matter how bad they are, your strategy will improve almost overnight. But if you don't write it down, it's incredibly challenging to improve your strategy.”

“engineering strategy comes down to like largely like two kind of core ideas. There's like a, a resource allocation, like how are you investing the headcount and the, you know, that the budget that you have, and then how do you make, um, how do you make decisions as they come up?”

“So in a lot of these cases, the way to drive up productivity is to reduce the burden around like a small number of like really high performers. But if those performers ever leave, your productivity is going to drop massively as, as well. And so it's sort of a high risk, high reward strategy. And again, doesn't really…”

“I think people want metrics to show reality. They want to show the truth, but half of metrics is showing the truth. The other half is educating people to inform their mental model about how the truth works.”

“something I believe pretty strongly is that teams should generally be one manager to like six to eight engineers. I think this is a really useful sizing mechanism.”

“And this is like one of the, to me, most predictive traits for whether an executive will last more than a year at a company. It's where they come in and they start with, Hey, can I, how can I change myself to fit versus how can I force my entire organization to fit to work with me?”

“typically when a CEO of a 500 person company feels their CTO is, is struggling, they're probably running into like one of, one of two different things. Um, either the, the individual CTO is like causing friction with other people on the team. For, for some reason, like their peers, or two, just like the, the shipping…”

“Anything else is going to get like a kind of consensus view, but like you don't need a consensus view on executive performance. You as a CEO need to have like a conviction view on like whether it's actually good or not.”

“But when you present to execs, you should start with the conclusion. And then, if they already agree with you, stop presenting. Like, there's no reason to keep presenting.”

“If you want, like, a high-quality exec meeting, you have to let the execs own the pace.”

“talking things through live when people do have the shared like context, they just disagree is incredibly valuable and it's almost impossible to kind of like get to the end of these things on like a chat on Slack or something. You, you really do have to like talk it out live for at least important decisions.”

“I think that the best folks presenting to executives start super zoomed out and then zoom in to their specific problem over the course of like 30 seconds.”

“testing a little bit with, um, Folks who have context that aren't the exec themselves is the easiest way to help calibrate.”

“Like we kind of joked earlier, like this isn't an industry that teaches you how to do things. It's an industry that gives you opportunities to learn how to do things.”