How to Adapt Your Design Process at Scale

Insights from FirstMark’s Design Driven NYC, a monthly event and community that lives at the intersection of design, user experience, and technology. Design Driven highlights the stories behind the most interesting products and designers in the world. See all of our Design Driven talks here.

When Jaime Strollo joined Betterment as a product design manager, the automated investing service had about 60 employees. In less than two years, headcount has more than doubled and its customer base has grown to more than 155,000.

Speaking at FirstMark’s Design Driven NYC, Strollo said that as the company gets more successful, the projects become more intense. The stakes get higher.

“As the stakes get higher, there are more people who want to get involved,” Strollo said. “All of a sudden, we’re having meetings we didn’t have to have before.”

In her experience, it has taken deliberate effort to scale the design process to keep up with the rapid growth of other teams throughout the organization. The key, however, has been to establish a clear process for ideation and iteration. A process that effectively sets and manages stakeholder expectations, while also drawing the best input and ideas from those same stakeholders.

Here are eight ideas for scaling design at a growing company.

1. Kick off strong. Betterment begins every project with a series of questions that help set the course for a project. What’s the problem we’re trying to solve today? What does success look like? How exactly will we measure success? What are our key constraints?

2. Assumption gathering. Strollo has found that explicitly documenting stakeholder assumptions is an invaluable exercise, particularly when it comes to building new features. Everyone involved in a project articulates their assumptions, even down to the very basic “We can build this,” or “People care this exists.” This longer list of assumptions is pared down to a short list of the riskiest assumptions; concerns that, if unaddressed, could send a project entirely off the rails. Through this exercise, the design team is able to surface the most pressing concerns from stakeholders at a very early stage in a project, and take proactive steps to address them (e.g., by vetting a project’s feasibility with engineering, or validating feature ideas with customers.)

3. Top 5s. In a “top 5s” exercise, participants take a long list of project requests and pick out five items to prioritize. It’s great for large cross-functional groups to establish — and agree on — what matters most for the design team (or any team, for that matter.) It also helps spur a ‘delete conversation’ — deciding which items should be removed from the priority list altogether. Items that are universally ranked low may not be necessary at all.

4. Ideation/Paper prototyping. There are a number of ideation and prototyping exercises that work well for groups. Crazy Eights, for example, gives participants 5 minutes to make eight sketches of possible interface designs. The exercise loosens participants’ creative muscles and surfaces a lot of ideas quickly. Strollo has seen success inviting other teams to a Crazy Eights exercise. Input from marketing, engineering, and others provides a diversity of viewpoints that can nix bad ideas early and draw out great, non-obvious approaches.

5. Managing feedback. In a growing company with lots of new people that may not understand designers or the design process, it’s easy to become overwhelmed with feedback. One simple approach: separate decision-makers from those that just need to be informed. That way, you can clearly establish what type of feedback — and if/how to address feedback when you get it— from every stakeholder, and keep a project moving.

6. Align feedback with company goals. Betterment deliberately frames design critiques against the backdrop of the company’s overall objectives and key results (OKRs). By structuring conversations as “this is the broader objective I’m targeting, these are the key results I want to get, and this is the product that gets us there,” you can approach design feedback with a context and framework aligned with a company’s overall vision.

7. Share early and often. The Betterment team embraces an agile approach to design. Rather than a grand unveiling and critique at the end of a project, Strollo’s team shares designs early and often. Customers and internal stakeholders see versions of a project at every step of the design process. Betterment leverages solutions like InVision (which FirstMark has proudly backed) to create and share fully interactive designs.

8. Invest in relationships. Arguably most important on Strollo’s approach to scaling design is building lasting relationships with customers and colleagues. Lasting relationships build empathy; a mutual understanding of others’ motivations, concerns, and desires. As your team, customer base, and ambitions continue to grow, you will face challenges you’d never expected. Investing in strong relationships pays off at every step of that evolution. Whether you are working on a new product or a new process, strong, empathetic relationships start new efforts on the right foot, sustain you through their implementation, and ultimately lead you to a successful conclusion.

To hear more from Strollo’s talk at FirstMark’s Design Driven NYC, see the full video above. For more stories and insights from FirstMark, visit our content library and subscribe on SoundCloud and iTunes. To learn about opportunities at FirstMark companies, please join our Talent Network.