Leading Organizational Change

"What I look for instead are things that can be gardened, things that can grow on their own and that you can direct or maybe give a little bit of extra energy to or curate over, and is a totally different mindset for it. If you do this properly, it looks like magic."

"The thing Cash App did right was like 10 things, not one. There were like 10 things that actually best in class, like insane talent density, insane focus, very strong at fraud, a lot of the way Brian, and Dustin, and Jesse, and Dangi tried to organize the amount... Like you know, with Jack's support was just really firewalled from the rest of the square, the hero customer was the consumer, not the merchants, so it was like literally in 100% of the trade offs the consumer's needs came first."

"I've slept on the floor in China before launching uberPOOL, and when you reflect the stress onto your teams, everybody tenses out. It counterintuitively doesn't produce better outcomes."

"But you think that customer research is all you need to build a product at a company, but figuring out how to create excitement internally and get buy-in from other teams because they're the ones that are going to build it. They're the ones that are going to help market. It's all a team effort."

"I've had CEOs who said, 'Well, it was the middle of the quarter, so we didn't start OKRs, but we did start Friday celebrations and oh my God, things are already changing. Things are already getting better.'"

"We have a head of AI operations. She's just constantly building prompts and building workflows that I and everyone else on the team are just automating as much as possible."

"Our whole parenting philosophy is resilience over happiness. When we're thinking about a resilient work culture, we want people who can say, 'This is hard and I can do hard things.'"

"And our team's like 15, 20 people, so it's just dealing with, we're going to be closing on 100,000 customers, and our support team's like three people. So we're trying to scale as fast as we can. So it's just kind of mind-boggling, just the scale of the demand, and how we've had to turn things around to match the demand as best as we can."

"What large companies don't do is when an experiment works, they don't go all in and double down. They try to keep hedging. We didn't hedge on AI. We said we were going to go all in."

"And those four people over the course of maybe nine months or so, built a time and attendance product. It was the only thing they were doing. They didn't have to worry about what was going on with our payroll product except to the extent they had to integrate with them a little bit. They were monomaniacally focused on this one thing and then identifying the places where yes, you, there's connectivity to the rest of the suite, and that allowed them to move extremely quickly."

"The sacred cows are like their own roadmap. What are all the things that you think we're not allowed to change? Let's start there."

"The biggest marker that I've seen between a botched layoff and a successful layoff is at the moment someone hears that they no longer have a job, did they hear it from their manager in a one-on-one? If that's when they heard it, it'll be okay. But if they heard it in an email, in a group chat, in any kind of thing where they were sitting next to or they're hearing it along with other people, it wasn't personalized, it wasn't one-on-one, that is terrible. That's when people get really angry and that's when they start going on to Twitter and going to newspapers and et cetera, because it feels dehumanizing."

"I do not recommend using SAFe. Every single person I have talked to who likes SAFe, found success with SAFe, they ended up ripping it up and making it into something else."

"If you're a large organization and you do some performance management process twice a year and you're 0 to 1 incubator, you've already killed it. It's the wrong incentive."

"You have to plan your chess moves out in advance. You have to really think before you act and build systems that were going to let you go sustainably faster."

"The company has a tendency to over-invest. Startups have the benefit of starving, and so you need to create scarcity. What we try to do is remind everyone things are going to fail, let's not drag the rest of the company into it."

"Now, evaluating success can look very different between early stage and established products. For a long time at Atlassian, we were treating everything a little bit equally in that the metrics success for the same."

"we had had a pretty entrenched consensus-based culture, where we would really debate a lot of decisions and a lot of features. And on the one hand, I think that that does lead to good outcomes, right? Thoughtful products that have a lot of viewpoints really baked into the core of the thinking. On the other hand, not fast."

"I think that we often treat engineers a little bit like children instead of giving them the responsibilities and ability to actually thrive as adults. And so like, "Oh, the engineers won't want to do that work." Well, that's actually not good for the engineers to be sheltered from what is important."

"Systems thinking is basically you try to think about stocks and flows. So stocks are things that accumulate and flows are kind of the movement from a stock to another thing."