Justin Rosenstein, Co-Founder of Asana, Talks Startup Success

Thank you.

Yeah, that's 300 million was... yeah. I think that success is a long series of problems. People often, I have to laugh when I get to the end of the day and someone asked me like, 'Oh, how are things going?' And if I zoom in on any particular day, it kind of just gets worse and worse. As the company gets bigger, you're always working on problems. There's always some obstacle in front of you. But as I said, the obstacle is the way. That is the path. It's just taking care of one thing after another. So if you zoom all the way in, it almost looks like every single day is nothing but challenges, nothing but pitfalls, nothing but obstacles. But then you realize, oh, but the sum total of those things, I am making progress. So I think one of the biggest things I've learned the hard way is just to not be discouraged by those day in and day out challenges and maintain that larger perspective.

Hmm. I think getting clarity of purpose and clarity of plan. So I do do a lot of things like the water exercise or these things that help to move faster. You do the buddying system too.

Yeah. I don't know about you, but I find, and I think different people are generally different, but a lot of people I know, it's just hard to maintain your focus on one thing at a time. And when you get to really tricky decisions, it's very easy to spin in your own head. So I try as much as possible to just not work alone. There are counter examples of course, but whenever possible, I think, okay, if it's a product decision, can I work with the relevant product manager? If it's some optimization question about how I'm going to spend my time today, can I work with my chief of staff to do that? And by doing that, I just find that pairing together you can often move more than twice as fast as you would have working side by side because you're able to keep your focus.

Yes, sudo budding is where you buddy with yourself. Just basically taking a journal and pretending that you're having a conversation with another person. So I'll write down a question that I have for myself, and then I will start to answer it, and I'll write the next question. It's a certain state, a key to keep a dialogue going back and forth with yourself. But that helps avoid the spinning on decisions.

Hmm, and that works for you?

But I think that the biggest thing is people often optimize for efficiency and figuring out how can I move as quickly as possible. And then people often spend 99% of their time focusing on how do I move as quickly as possible and only 1% of time think about which direction am I going in the first place. And I think that's a very skewed ratio because so often people move really quickly toward their destination only to discover it's not the destination they wanted in the first place. So I think the biggest time-saving thing I can recommend is making sure that you carve out the time to reflect and think carefully: what are we trying to accomplish in the first place, why do we want to do that, and what is the optimal strategy to get there?

Yeah. I think the first thing is to remember that success is a series of problems, that problems are inevitable and problems are solvable. And it is just so easy to get into this mindset of starting to think, 'Oh, maybe this isn't working.' And obviously there are some businesses where it isn't working and it's hard to know. But I know so many leaders that I talked to, and I asked them like, 'When did you know it was gonna take off?' And even really successful companies, they're like, 'Still waiting for that moment,' because there's so much in the thick of the challenges. So just keeping that bigger perspective. Similarly, I think early on in starting a company, I suffered from this. I think most of the people I talk to, most leaders I talk to, suffer from this at some point in their lives: impostor syndrome. You get to this point where people you're hiring, they're looking to you for leadership and guidance, and part of you starts to wonder, 'Wait, have I boozled them into following me? What's going on here?' But I've been in rooms with incredibly successful people and just bluntly asked, 'So if any of you struggled with impostor syndrome,' and every single person would raise their hand. So knowing that has been comforting to me enough that I don't really experience it anymore. But there were a few years there where every time my mind would be like, 'Maybe I don't know what I'm doing,' I would then, as a meditation practice almost, remind myself, 'Okay, that's something that human beings experience when they're doing things like this.' And so bringing it back to, 'Okay, maybe no one knows what they're doing, and maybe I know as much as anyone does.' And then leading from a place that combines both deep humility and a deep meta confidence. So what I mean by humility is I think leaders can sometimes get to a point where they think they're supposed to have all the answers and they become closed off to the opinions of advisors or the opinions of employees. So maintaining a deep intellectual humility of, 'Look, no one really knows anything for certain,' and so being open-minded to changes in the market, the feedback you're getting from your peers, feedback you're getting from teammates, was really valuable. But if you just have humility, you can start to lose your confidence. And so having this kind of meta confidence, not confidence necessarily that you already know what you're doing, but the confidence that you have the ability to develop the skills required in order to navigate new challenges, in order to learn about new obstacles and be able to overcome them. And so with both humility and that kind of confidence, I think you can almost anything.

Yeah, you need a hundred percent of both. Equals two hundred percent. Multi-dimensional matrix of virtue.

Thanks so much.