Asana’s Justin Rosenstein on the One Quality Every Startup Needs to Survive

Asana’s Justin Rosenstein on the One Quality Every Startup Needs to Survive

Asana Co-founder Justin Rosenstein on the critical need for clarity within startups and how to achieve it as you scale.

Justin Rosenstein (right) wasn’t sure what had happened. One of his company’s highest performing engineers seemed to have lost his enthusiasm for the work. “He had gone from super dedicated to detached,” says the co-founder of Asana, an app that powers teamwork without email. “Something wasn’t right. He seemed to be in an existential funk.”

So he took him for a walk and asked one simple question: “What’s wrong?”

At first, the engineer couldn't pinpoint the source of his malaise. Then he said, “I’m not sure what I’m doing here. I wonder, should I even be writing software?” Rosenstein was struck. Sure, the company had grown, but what had changed?

Instead of reciting a normal pep talk, he started asking questions. “When you go back to your desk, what’s the next line of code you’ll write?” he asked. The engineer explained he was repairing a chunk of old code. “Why?” Rosenstein asked. And with every answer he asked again, “Why?” Finally the engineer said, “It will make the site faster, which will let people communicate with their teammates more quickly.”

This was the breakthrough. “So it will allow more people to accomplish their goals?” Rosenstein asked. “I looked at him, and he looked at me, and it was just like, okay, he was ready to get back to work.”

He had stumbled upon that one, critical missing ingredient — an ingredient that Rosenstein and Asana’s leadership have accepted as key to their success: Clarity.

“People have spent the last decade wringing efficiency out of technology,” says the former Facebooker-turned-founder. “This next decade will be about bringing more efficiency and productivity out of the humans who use this technology. We haven’t optimized the human input yet. Getting there will be about creating clarity.”

In an ideal world, you’d be able to walk up to any one of your co-workers and get the answer to the following questions:

  • What are you working on right now?
  • Are you confident that it’s the most important thing you could be doing?
  • Do you know who is waiting on you?
  • Do you know to whom you can go for support?
  • Do you know how your work fits into the overarching product we’re trying to accomplish?
  • Do you know why that product matters?

But this is seldom the case, even at the most efficient, productive, high-profile companies. Rosenstein cites a McKinsey study showing that 30% of the average worker’s time is spent on email alone. Another 20% is spent tracking down information that someone who works in the same building already knows.

If people don’t have true clarity around what they're doing and how it fits into their organization, they’re bound to duplicate efforts, deflate morale, spend hours on unimportant tasks, and more.

To combat this problem, Rosenstein says, leaders need to prioritize clarity in everything they do in this order: Clarity of purpose; clarity of plan; and clarity of responsibility. If you can marry these three qualities, you can achieve organizational fluidity that will get the most out of your resources.

Clarity of Purpose

“I find that, depressingly often, you’ll ask someone why they are working on something and they don’t know the answer. They’ve totally lost touch,” says Rosenstein. “Think about how disheartening this is on both sides.”

Making it clear how everything fits into a broader, higher, deservingly ambitious goal has to be your number-one concern as a founder. Only when you do this can you trust the people you work with to make good decisions, from the micro-level up.

“Let’s take engineers working on incremental features: If they can see how this will directly affect the overall user experience, they can make decisions that are better connected to what everyone is doing.”

A lot of people talk about how every piece of work has to have an invisible thread leading back to the company’s mission. But it’s surprising how easily this gets lost in translation, especially the more granular the task. To a large extent, this is what had plagued the disaffected engineer whom Rosenstein took for a walk a year ago.

Kenny Van Zant leads business and corporate strategy efforts for Asana, and has made reinforcing clarity of purpose one of his key objectives. It’s stressed everywhere, especially at all-hands meetings, where every staffer who presents to the company is required to clarify how a given project fits into Asana’s dedication to helping the working world thrive. That inspiration is what fuels good work, Van Zant says.

And as reliant as Asana is on digital communication, it breaks away from this to ensure that everyone is rallying around a common cause. Every Friday, the team gathers and everyone shares one thing they are excited about in their work. “It’s an opportunity for everyone to reflect, celebrate an accomplishment, or get positive feedback while also learning about what everyone else is doing,” says Van Zant. “It’s a chance for us all to see what makes people happy, what we should be doing more of, and it energetically synchronizes the team.”

Clarity of Plan

Once you have vision, you have to work on executing it. While inspiring people may be your most important task as a leader, bringing that inspiration to life in an orderly, efficient way is the hardest of them all.

“I’m amazed by how often I talk to people working at big organizations and when they ask very basic questions like ‘What are the steps we need to take between now and accomplishing our goal?’ or ‘What do we need to do to make XYZ happen?’ no one knows the answers,” Rosenstein says.

Kenny Van Zant joined Asana in 2011 to lead functions outside of product and engineering.

Van Zant, a veteran of large corporate organizations, is all-too-familiar with this problem. “When people don’t know the order of operations, you get confusion, tension, drama. People get territorial because someone is already doing what they think they should be doing. And all you see are emails and meetings asking the same question over and over, ‘What are you working on this week?’”

There are several ways to guarantee clarity of plan, as Rosenstein sees it. You could religiously gather everyone together and enumerate every single thing that needs to happen between now and project completion. Or you could do this in one central, digital repository. This could be tracked in a text file, or on Google Docs, or using Asana's application. Regardless, the important thing is that it remains dynamic and extensible without getting too long or onerous.

“You can’t treat plans as something static — an authoritative plan of record,” says Van Zant. “You have to be able to add to it whenever you think of something new so that nothing slips through the cracks.”

Rosenstein has a lot of experience with this. He recalls one of many instances — this one at Google — where he realized there were about 30 things left undone the day before launch.

“This thing was definitely going to happen — there was press already scheduled. There was no choice,” He says. “The question became: What state did we want the product to be in when it did go live? This was a product that could have either been really significant or really embarrassing. In the end, the team and I pulled an all nighter.”

As bad as this was, the underlying problem was worse: No one knew how all the little steps and necessary tweaks got missed along the way. “Google and Facebook are among the two most organized, capable companies possible, but even there the expectation was if you were shipping product the next day, you didn’t make dinner plans because something would probably go wrong. It was still ‘all hands on deck.'”

When Rosenstein and his team reflected on the chain of oversights that led to their all-nighter, they realized that the steps to accomplish their goal were scattered — fragmented among many separate to-do lists, Post-It notes on people’s desks, a smattering of Google Docs, in people’s brains. There was no one place where the list of musts was written down with the ability for people to comment, or annotate, or add.

This type of reflection is vital to clarity of plan. “You want to make sure you review everything that happened so that you’re always improving a little bit, always getting a little bit better, always less likely to make the same mistake,” Rosenstein says.

To encourage this type of reflection, Asana (the company) has broken from traditional quarterly and annual planning. Instead, the company has what it calls “episodes,” and each episode is dedicated to planning the next chapter of the company, from product to recruiting. Every episode also kicks off with a full week of meetings called “roadmap week,” and everything that happens during the subsequent episode starts there — with very few meetings (if any at all) afterward.

To create insightful plans for an episode, the Asana team breaks into cross-functional committees, each tasked with taking on a different part of the company or product. There are committees for everything from business development to company values. Together, these small groups look back at what was done during previous episodes, steer new goals to fit with the company’s core values, and make recommendations for what should happen next. These recommendations are then tweaked and/or approved by leadership.

As a result, everyone feels like they have a stake in the direction of the company, people from across the org get to learn more and express fresh opinions and ideas about things they’d never otherwise be exposed to, and — most importantly — everything gets diligently documented so that it can be accessed and modified by anyone as things progress.

Clarity of Responsibility

When you don’t know who’s accountable for what, the chances of dropping the ball at critical moments are exponential. “You hear it all the time — ‘I thought so-and-so had the ball on this project’ or two people thought they were carrying the same ball and they come to you and say, ‘I stayed up all night working on something that someone else already did.’ That more than anything else can kill momentum,” says Van Zant.

Clarity of plan may be all about compiling a master list of what you need to get done, but without clarity of responsibility none of it will matter.

“It’s important that you have a single individual responsible for making sure a task gets done,” says Rosenstein. “Apple calls this the directly responsible individual model [Amazon champions something similar] — and the important thing is that it’s just one person.”

If zero people are responsible for something, nothing happens. If two people are responsible, it probably still won't happen.

You need a point person who feels deeply that it is their responsibility to bring a project over the finish line. And this isn’t about simple delegation, either. It’s one thing to assign a task to someone, it’s another thing to get his or her commitment to finish it. “As a leader, it’s your job to get people to feel this commitment,” says Van Zant.

This is where deadlines come in. “You need people to make commitments in terms of 'what by when,'” says Rosenstein. “When you have clarity around who is doing what by when, you get all these emergent effects. Projects run smoothly. You start to develop a culture of responsibility. Even if people have to depend on others to get their project done, they will make sure these people are on top of their game too.”

Delegation and deadlines are common enough in corporate culture, but they aren’t often omni-directional. Orders come down from management. Employees execute and come back for more. But this structure was made to be broken. And in order for your startup to succeed, it really needs to be, Rosenstein says.

You should be able to tell any person, a co-worker, your boss, anyone, 'You do this.'

“You need to be able to tell someone, ‘Okay, now you have the ball.’ This attitude can’t just flow downstream. You need to be able to assign work to your boss. It’s critical that you eliminate the baggage around who is allowed to assign what to whom. Why would you want to work at a company where you can’t ask anyone to make a commitment to helping you?”

"When you have a manager always delegating to reports, you see them only tapping a small portion of their organization's potential."

“In traditional organizations, you see responsibility become additive at the higher levels,” says Van Zant. “You see the one person in charge taking on responsibility for every single decision that every single one of their reports makes. Suddenly they’ve taken on a bunch of work that isn’t really theirs — they’ve taken on all the accountability and all the stress.”

You can diffuse this tension by diffusing information, Rosenstein says. When the details of projects, including who is responsible for what, exists outside a manager’s head, and you make all this information available to everyone, you spread out accountability. It suddenly becomes very clear when someone has dropped the ball, or if someone doesn’t have time to take on more work, or if more steps need to be taken before launch. Everyone is responsible for seeing and understanding the situation.

“When management is freed up, they can focus their energy on more important things: Developing their people, providing important context around projects, upgrading tools,” says Van Zant. “They’re no longer spending all their time and energy simply serving as an information conduit. If your manager already knows what you’re working on and the status of your work, you can use that meeting time that would otherwise be about what you did that week to talk about how you want to develop in your role, how you want to participate in the future of the company, etc. This is how great companies grow their futures.”

Omni-directional delegation has several other positive side-effects. People no longer feel isolated; it’s easier to take advantage of their full range of capabilities and knowledge; and people who are closest to the work — usually those at the bottom of the totem pole — can feel comfortable steering projects from the bottom up.

In this sense, clarity of responsibility fuels autonomy. When people are given ownership over a project, or even one piece of a project, they are empowered to do their best work.

The AOR has become a pillar of Asana's company process.

To promote clarity of responsibility, Asana (the company not the tool) has built a master list called the AOR — standing for “Areas of Responsibility.” It is literally a list of all the things going on inside the company, every area of focus and who owns them. The list runs the gamut from who owns product security to whom to go to with questions about benefit plans.

A fringe benefit: Every time the company onboards a new person, they can simply point them to the AOR, which is completely tagged and searchable in Asana the tool, so they can get almost all of the typical “new employee” queries answered right away. They don’t have to waste any time asking around about who knows about what, or who is running point on what project. They can just dive in.

It’s never too early to build your company’s version of the AOR, Rosenstein says. If you’re just starting out, your list might only contain 20 things. But every time someone sees something they want to do or that the company should be doing, they can add it and claim responsibility for it. Eventually you’ll see the list grow to 50, 100, and way beyond that. If he has one trick for young companies, it’s to use this type of tool to lay a strong foundation for keeping track of everything — before it has a chance to spin out of control.

The best thing a small company can do right now is identify who is carrying the ball on X project. You'll be surprised how much confusion that clears up.

What’s equally surprising is how many founders don’t understand how important this is. “It’s easy to let things go when you’re thinking, ‘Oh my god we only have three months of runway, we have to go, go, go,’” says Rosenstein. “Founders think, ‘we don’t have time for clarity.’ But really, you don’t have time not to think about it. Once you have the right processes in place, maintaining clarity will only take about 5 — maybe 10% of your bandwidth, and the payoff is huge.

“If you don’t establish the clarity precedent right away, it will never happen,” he concludes. “Even if you’re just at five employees, you should already be thinking about it.”