How Roadmap Week helps us turn big ideas into reality

Originally published on Wavelength, a publication by Asana for teams who aspire to do great things together—through a mindful, purposeful approach.

When Asana was a young company of just a few people, we experienced a phenomenon that’s common with early-stage startups. Just about every day, someone would come to work with a new idea. (A good idea, no less!) Most of the time, we said, “let’s do it.” Until we got distracted by the next new idea.

On the one hand, it’s hard to make meaningful progress when you’re constantly open to changing strategy. On the other hand, rejecting all new ideas is the opposite of fostering the kind of organization that can learn, adapt, and react quickly.

That’s why setting aside time to make meaningful, structured work plans—and then carrying out those plans—is so important. At Asana, we consider the planning process to be just as critical as the execution process. You wouldn’t run a race without a route. Similarly, it’s difficult to run an organization without mapping out clear goals.

Sketching out a roadmap

There are many ways to do planning. After years of prototyping our own systems, we’ve landed on a model that works well for us, and that may work well for you too. We structure our calendar into ~4-month periods we call “episodes.” During each episode, we stick to our plans. As new ideas come up, we write them down and table them for later.

In between each episode, we hold a weeklong event called Roadmap Week. Roadmap Week is when we reflect, integrate new ideas, and plan just how we’ll carry them out. The whole company comes together for both high-level reflection on how the last episode went, and high-level planning on how the next episode should go. It’s a time to dream big and review all those ideas we wrote down over the past few months. Large strategic pivots are now on the table.

The week is driven forward by committees that facilitate a series of meetings focusing on everything from deployment and scalability to metrics and design. We take an honest look back on our successes and failures, discuss our goals and deliverables, map out the next episode’s key milestones, and envision new ways to experiment. Because we consolidate many meetings into that week, we have fewer meetings throughout the rest of the year.

Sometimes people say, “I don’t have time to do these kinds of planning exercises.” We’ve found that we don’t have time not to do these exercises. Without a clear plan, you might find yourself running a race without a route—perhaps quickly, but in the wrong direction.

Ultimately, organizations exist to accomplish goals. Succeeding at those goals comes down to being clear about exactly what you’re trying to accomplish (“clarity of purpose”) and how you’re going to get there (“clarity of plan”).

Here are some of the major ways we’ve benefited from implementing Roadmap Weeks.

Learn from your failures.

We look carefully at our ideas and goals set forth during our previous Roadmap Week, and inevitably, many of them won’t have come to fruition. That’s okay: You can often learn more from failures than successes. Deconstructing where, and why, something went wrong gives you the chance to both identify warning signs and avoid similar courses of action in the future.

But also from your successes.

Of course, it’s just as important to recognize and celebrate our achievements so we can replicate them elsewhere. Looking at how ideas were implemented successfully means we can use similar approaches that will lead to more successes.

Lean into big, bold ideas.

Roadmap Week is our chance to look at all of the big ideas that came up during an episode, and evaluate them objectively. In the course of an episode, I personally will generate five new big directions we could take the product; they all look great when they’re shiny and new, but by the time Roadmap Week rolls around, only one of them will seem actually worth pursuing. Once we identify the ideas that have staying power, we sketch out a realistic work plan, and put individual next steps in Asana.

Collaborate with teams that otherwise wouldn’t work together.

Roadmap Week is an opportunity to bring together individuals from teams that don’t normally interact day-to-day. It’s a chance to hear from people from different parts of the company, who might have ideas about areas they don’t normally work on. For example, often a product team will present an idea for a feature, and someone from our customer success team will be able to correct their assumptions about what customers actually want from the feature.

Anticipate problems.

In mapping out how to execute a goal, it’s worth brainstorming all the potential roadblocks that could impede you. These obstacles can often be gleaned from past failures. Other times, they’re determined by vividly imagining just how certain scenarios will play out. “Pre-morteming” is surprisingly effective: Pretend it’s four months from now, and the project has failed; what went wrong?

Capitalize on collective energy.

Roadmap Week is not only a reset; it’s a time for teammates to come together, celebrate all you’ve accomplished, and enjoy the freedom of open-ended creative exploration. Ideas produce inspiration, and inspiration produces dopamine ;-). It’s a pleasure to harness the collective passion and excitement that comes out of dreaming big, together.

Read more from Justin Rosenstein and his global collaboration initiative One Project.