Asana Co-Founder Justin Rosenstein Goes Deep On Mindfulness and Why It’s Crucial For Founders & Their Companies

Justin Rosenstein, Co-Founder of Asana

Justin Rosenstein is the co-founder of Asana, the fast-growing work tracking app for teams. He’s also the primary author of Wavelength, an online publication for teams who aspire to do great things together — through a mindful, purposeful approach.

At Awakened Founders, it’s our mission to help startup founders and leaders tap into their innate genius so their companies can achieve their highest potential for positive impact in the world. We do this through executive and mindfulness coaching, as well as our Conscious Balanced Leadership corporate program.

Mindfulness is a core component of how we work with our clients, and while many studies have confirmed the importance of it for increasing focus, reducing stress, and improving general well-being, many in the tech industry have yet to integrate a regular mindfulness practice into their lives.

We set out to interview founders, executives, and people who work in tech about how mindfulness has changed their lives. We’re excited to present our interview of Justin below. Enjoy!

What does mindfulness mean to you?

Making new choices in a mindful way can allow you to be much better at navigating complex terrains.

It seems to be that the default state of the human nervous system is one of reactivity; of just going through life continuing to exhibit whatever behavioral patterns you exhibited before.

Mindfulness is the skill of actually noticing what’s going on; tapping into an expanded awareness such that you can make new, different choices in response to the same situations; choices that are more consistent with your values and goals.

At a company level, often from the outside you’ll look at a company that gets disrupted, and you’ll ask “how could they have been so stupid?” It’s not that they were being stupid, it’s just that any given day, doing the thing they did the day before makes sense! Making new choices in a mindful way can allow you to be much better at navigating complex terrains.

Similarly, with culture, often you’ll go to companies and people can tell you what’s wrong with the culture. Then a year later things have gotten worse and there are lawsuits and you ask “how could you have not noticed that these things are happening?” They probably just didn’t take the time to develop the practices as individuals or as an organization to be able to pause and tune into what’s really going on.

The traditional use of the term “mindfulness” is a state of subjective awareness of the present moment. You can instill that kind of awareness at the organizational level, where you create practices to actually pay attention to and measure what’s going on, whether that’s how your customers are reacting to your product, or how employees are experiencing the culture of the company. Once you have that information you can say “ok, now we’re going to make mindful choices about how to proceed”.

How have you used mindfulness practices to influence the culture at Asana?

When people join our team they’re educated about the concept of equanimity. I think I take it for granted at this point, because a lot of people who join the company just marvel at the fact that we handle problems so calmly here.

Everything from the micro of how we interact with each other to the macro of how we structure things within the company.

On the micro level, one of our values is equanimity, which is a natural corollary to mindfulness. I think of equanimity as an emotional “okayness” with things as they are, and an “okayness” with however they will be in the future.

There’s a really important distinction here: people often think you have just two options. One option is you can be really passionate and care a lot about what you’re doing, and when things go well you’re really stoked, and when things go badly you’re really upset. On the other extreme is option two, where you don’t care that much, you’re not that passionate, you’re kind of apathetic. If things go badly.. “eh”.. you didn’t really care that much in the first place, what’s the big deal. People think you have to choose a culture somewhere on this spectrum and if you think these are your only options, then when you’re starting a company you’re going to choose to be on the first end of that spectrum.

I see a third option: you can decouple passion from attachment. Equanimity is the opposite of attachment. This is pretty much the thesis of the Bhagavad Gita, this decoupling. With this third option, you can be extremely passionate, give something your all, and at the same time be equanimous: deeply ok with things as they turn out. In our experience this third option actually helps our ability to succeed in our goal, because all the effort spent stressing and worrying and getting yourself riled up is energy that would be better spent just passionately trying to achieve the goal.

In entrepreneurship, things always go wrong. Success is a long series of problems, always. And so, if you’re in the game of entrepreneurship and every time you have a set back you end of wasting a bunch of energy getting upset with yourself or your team, instead of spending that energy being like “ok, something went wrong. Let’s mindfully investigate what went wrong. How can we do it better?”. Mindfulness just leads to better outcomes and you’ll be more likely to achieve your passions.

That’s at the smaller level. What this looks like in practice is sometimes hard to put a finger on because it’s not like you can have corporate policies, but we do talk about it and we live it at Asana. When people join our team they’re educated about the concept of equanimity. I think I take it for granted at this point, because a lot of people who join the company just marvel at the fact that we handle problems so calmly here. They’ll say things like “well back at my old job, if something like this came up people would be yelling at each other, there would be a lot of mistrust, people would be upset”. At Asana we’re just like “ok, let me take responsibility for that, let’s talk about what would be better in the future, and then we move on.”

We take this all the way up to the scale of the whole company. We have a process called roadmap week, where every 6 months we take a whole week to stop, reflect on where we are, and where we want to go and make conscious choices.

At this point the company is big enough to where we have different roadmap committees for each product and aspect of the company. A lot of companies will say “well I don’t have time to take a week to sit around and think about this stuff.” We’re always like “we don’t have enough time NOT to”.

When you don’t take that time, you’re probably going faster, but you’re likely going faster in the wrong direction. The path to success is rarely a straight line. Roadmap week allows us to fully commit for 6 months and then know that we’ll be able to pause and reconsider and course correct.

I don’t know if there is research backing this up, but almost anyone I know who meditates will anecdotally report that you actually get more done on days where you stop and take the time to meditate. If I’m like “oh I don’t have time to center myself today” I just spend the whole day in this slightly frazzled off center state and I don’t get as much done.

A common image in Buddhist art is the wheel. Back in the day when people were manually making these wheels, the hub was often just slightly off center. The more off center it was, the more the cart would go “clu clunk, clu clunk, clu clunk” and slow you down as you pushed it. The more you took your time to center the hub, the more smoothly your ride would be and you’d end up at your destination quicker. I think this analogy applies well to how we work today. The little bit of extra time you spend getting your craftsmanship right, or in our case centering yourself in your own subjective experience, the bigger the payoff will be because you’ll be able to move so much more smoothly and efficiently.

How has mindfulness changed you as a leader?

The more centered you are, the more you can empathize with people, and there’s an old saying “people don’t quit companies, they quit managers”

It’s so deep, it’s hard to know where to even begin. Certainly, I’ve found equanimity to be essential. In some ways I’m impressed with successful entrepreneurs who don’t have a mindfulness practice, from the perspective of “damn, it’s hard enough WITH a mindfulness practice, I can’t even imagine doing it without one.” Entrepreneurship’s just hard. You’re constantly facing struggles. Asana’s really succeeding as a business, and it’s still just constant problems and stresses.

The ability to step back, zoom out, take the bigger view is really valuable. The more centered you are, the more you can empathize with people, and there’s an old saying “people don’t quit companies, they quit managers”. I think that happens when they don’t feel like their manager is really listening, really understanding, really looking out for their best interest.

It’s very easy to understand how that could happen if you’re an entrepreneur or an executive. You’ve got so many things going on there’s so many things you’re juggling that it’s easy to just start to see the people you work with as cogs in the machine. By taking the time to stay centered and be mindfully aware you tap into what other people are going through, and you see them in a more deeply human sense, which leads to better outcomes. Companies are built on human relationships.

Can you speak to why having a mindfulness practice allows you to get more done?

There’s data that backs this up, like taking breaks in the middle of your day does increase your total productivity. My subjective experience of it is that if I’m in the zone, if I’m in Flow, if I don’t have a bunch of background chatter in my head going on, and I can just look at the task at hand and joyfully proceed to execute on it, then it often doesn’t take me that long.

If I’m multitasking or thinking about 5 different things, and I’m stressed, and biting my nails, and worried about whether I’m smart enough to pull this off, or whether people will like it after it’s done… all of that mental chatter creates this big fog that makes it very hard to execute.

Sometimes it almost makes me laugh, if I have a day where I’m particularly off center. Things that seemed just insurmountably painfully hard are just not that big a deal if I’m feeling centered the next day, and I just laugh at myself that I took an hour procrastinating this thing that only took 20 minutes.

What kind of advice would you give a founder or someone at a smaller company who doesn’t have a mindfulness practice?

If you’re a knowledge worker — if you use your mind for a living — then to not take the time to train and to get your mind to be in good shape is just a poor business decision.

There’s two parts to this. One is getting someone to believe that it’s worth developing one, and the other part is developing one.

The ability to get more done, be happier, more focused, to be able to strategically pivot and make better decisions, and even to be much more creative, because when you’re in that flow, creativity is a natural human state — this all makes a clear argument for developing a mindfulness practice.

It’s impossible to imagine a professional athlete saying “I don’t have time to train”. If you’re a knowledge worker — if you use your mind for a living — then to not take the time to train and to get your mind to be in good shape is just a poor business decision. At the human level, there is this technology [e.g. meditation] that has been developed over thousands of years that allows you to maintain your center and your joy, even in the face of great challenges. I’m really glad that I’ve employed that technology and I think others will enjoy it too.

Having made the decision that it is valuable, you’re left with the tactical “how to start”. I’ll tell you the way I was able to start my practice: there was a year when I intellectually had this sense that it would be good if I were meditating everyday. I was having a conversation with Dustin’s girlfriend at the time, about 9 years ago, and we were both saying that we felt like we wanted to start meditating. I said, “Cari, how about this: tomorrow and each day, when I meditate, I’ll text you that I meditated, and when you meditate, you text me that you meditated.” She said, “Well what happens if we miss a day?”, and I said “nothing, just do it the next day.”

So it’s not really an accountability buddy, it’s just like a “presence buddy”. Someone you know is out there listening. We still continue this 9 years later, texting each other more than 50% of the time, for sure. So I definitely think the buddy system works.

Any last tips you’d like to convey?

There’s a whole article that Dustin wrote called Mindful Asana that does a thorough analysis of how we apply mindfulness in the corporate setting. It affects everything from how we use “5 Why’s Processes” to investigate failures, the way we choose to empower people, the kind of authenticity we have at work, the levels of candor, the downsides of working all the time where after 50 hours you’re not actually going to get more done. Dustin also wrote an article Work Hard, Live Well. From what I can tell the companies where people are working more than 50 hours a week consistently, they’re getting the worst of both worlds: they’re not getting anything more done, and they’re burning their people out faster.

If you’ve gotten this far…

Thank you for reading! If you’re a founder, exec, or leader and want to learn how to achieve your goals and grow your company from a space of mindfulness and presence, contact us at Awakened Founders for a free consultation: Service@AwakenedFounders.com

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