Where Design Breaks as Startups Scale

And How to Avoid These Pitfalls by Democratizing the Power of Design

Elijah Woolery
Aug 5, 2019 · 9 min read
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For most of my career, I’ve worked as a designer at very small companies and startups, ranging from the roughly 40-person team at Light and Motion in the early 2000’s where I designed underwater camera equipment and bike-lights, to a short-lived but highly educational experience at my own 2-person venture-backed startup in 2012. The latter experience gave me a huge appreciation for HBO’s documentary series Silicon Valley.

In my current role as director of design education at InVision — which is by far the largest and fastest-growing company I’ve worked for — I’m lucky enough to talk to design leaders at a wide variety of companies and various stages of growth. From our Design Better Podcast, to initiatives like the Design Genome Project, and our yearly Design Leadership Camp, our team gets to learn from the best practitioners of design and share their strategies and tactics to a broad audience.

Along the way, from my own experiences and from sharing the experiences of other design leaders, I’ve seen three different places where the design process and design teams can break as startups grow into larger companies. I’ve also observed the way leaders navigate these challenges, and help their companies scale design practices successfully. In this article, I’ll share these stories and strategies with you so you can bring them back to your own team and, with a bit of luck and hard work, avoid the pitfalls that have tripped up growing startups and companies.

Understanding the customer

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A white-tip reef shark, from a photo trip to the Socorro Islands south of Baja California.

As a product designer and design engineer for Light & Motion in the early 2000’s, I got to test underwater cameras in exotic locations, take some fun pictures, and flood expensive equipment with salt water occasionally in the process. Our company, founded by serial entrepreneur Michael Topolovac, was focused on creating the best possible professional-grade equipment for underwater photographers. We wanted to enable our customers to be the hybrid offspring of Jacques Cousteau and Ansel Adams (just don’t imagine the baby pictures).

The company often struggled to find these elusive customers. Frankly, there just weren’t that many of them out there. Michael considered himself the target audience for the product, but as he likes to say after founding two other successful companies, “a founder does not proxy a market, unless they’re Steve Jobs.”

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Ansel Adams vs. Kim Kardashian.

If we had just taken the time to talk to the customers — to understand the real needs and jobs-to-be done for the equipment we were designing — we would have understood that the vast majority of them just wanted to easily capture and share their diving adventures. They wanted to take underwater selfies. They were closer to Kim Kardashian than Ansel Adams, and we missed out on a huge market that GoPro eventually captured.

This is an unfortunate and common mistake among startups. Often, when a founder creates a new product, they’re doing it from a desire to solve a personal problem or need. And that’s just fine; many of the most successful startups began that way: Facebook, Airbnb, DropBox. But the problem occurs when there’s a missed opportunity to connect with customers and discover an even larger market, or serve your existing market with a better experience.

So how do you stay connected with customers, even if you’re at an engineering or technology-driven startup? At Google in 2012, Margaret Lee led a design team working on Google Maps. She was given a mandate from her boss at the time to have everyone on the 100+ person engineering and product team participate in user research.

In an interview from InVision’s first Design Leadership Camp, Margaret Lee discusses Google’ Project Pokerface, a way to get their engineering team involved in user research.

They called this experiment Project Pokerface. Every engineering team was taught basic user research techniques, and assigned to speak with users for three hours every week. The results were pretty amazing: not only did teams get excited about discovering unknown bugs in the software, but they came back with much greater empathy for the people using their products, which translated into better experiences for the users.

As Jared Spool of UIE notes, from his multiple studies of the effects of user research, it is most effective when non-designers also get to participate in these efforts:

“It’s from direct exposure to the users that we see the improvements in the design.”

Getting buy-in for design

When Margaret’s team ran her project, Google had already begun to invest more in design. But back in 2006, they were still very much an engineering and efficiency-driven culture, where design was often an afterthought. This was around the time that Irene Au joined the Google design team as a leader, after a pioneering career working on influential projects like the first commercial web browser.

Google was growing fast, but Irene wasn’t able to hire enough designers to make the impact she wanted her design team to have. She spoke to Larry Page and asked him what his ideal user experience for something like email was. He mentioned Pine, a command-line interface e-mail client for UNIX (an interface that my classmates and I suffered through as undergrads in the 1990s).

If you’ve got a technical mindset, are fast on a keyboard and good at memorizing shortcuts, Pine could indeed be a wonderful experience. But most of Google’s users didn’t fit that profile, and Irene and other designers advocated for products that would address the needs of more of their users.

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Gmail’s design evolved drastically between 2006 and 2012, driven both by bottom-up efforts from design leaders, and an eventual top-down embrace of design principles from Larry Page.

Over time, Larry began to embrace design principles like using white space effectively to direct the user’s attention, while giving the eye somewhere to rest. By the time Project Kennedy was completed in 2012 — a company-wide redesign of their suite of products — he went so far as to say that “our goal is to design everything so it’s beautifully simple.”

Even if you have top-down support for design, it can be challenging to get an entire organization to buy-in to its benefits. When Steve Jobs returned to Apple in 1996, the company was making thirty-two different models of PowerPC, with no real vision as to why. So he immediately did two things: he cut the product line drastically, and he helped create a new vision for the company: Think Different.

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Images from Apple’s Think Different ad campaign.

In addition to being a highly successful ad campaign, this also served as an internal motivator for teams to understand why they were building the products that they were building. They were building tools for people who thought differently. People who were innovators, explorers, wildly creative. Not thirty-two beige boxes designed with nobody in mind.

As a designer or design leader, how can you go about helping establish the vision for a new product or feature? It comes down to telling a good story. And one of the best tools for this is storyboarding.

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Early storyboard concept for Arrival (via Kickass Canadians)

If you haven’t used storyboarding as a design tool before, you may think that they are the territory of fast, capable illustrators who outline epic scenes for Steven Spielberg or Denis Villeneuve. And didn’t Airbnb go so far as to hire a Pixar artist to create their product storyboards?

Sure, if you have the budget, high-fidelity storyboards can be a great vision artifact. But they can potentially be even more powerful as a tool that everyone can participate in, not just skilled designers or illustrators. If you can draw a stick-figure comic on the level of XKCD, you can make a storyboard. And just like user research, it’s far more potent to include people outside the design team in the process to give them a voice and input early so they have context and ownership later in the product development process.

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A storyboard created in InVision’s Freehand, to test design community program ideas

At InVision, our team creates storyboards collaboratively in Freehand, and we use them as a prototyping tool during design sprints. We test these storyboards with our audience to get feedback and gauge reactions. Whether you’re working together remotely with a tool like Freehand, or gathered together in a conference room with your team and other stakeholders sketching out a storyboard on a 3M Easel Pad, collaborating on storyboards is a powerful way to set product vision and prototype new ideas.

Sharing your LEGOs

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My three brothers, Halloween circa mid 1980’s

I grew up with three younger brothers. My middle brother is four years younger than me, and he called the twins — who came along two years after he was born — “the two guys, the bad guys [sic].” He’s dressed up as a lawyer in the picture above.

As kids, we were all obsessed with LEGOs. The challenge was that we had a somewhat limited supply of any given set. This was back in the days before licensed Star Wars or Marvel sets were a thing; it was just generic “Space” or “Castle.” Being the older brother, I would often hoard the LEGOs to create elaborate facsimiles of X-wings and Tie-fighters.

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Painstakingly built LEGO creations didn’t typically survive my brothers for very long. Original LEGO Millenium Falcon destruction video via Wired.com.

Inevitably, these creations wouldn’t have a very long shelf-life, and after several frustrating years of watching my LEGO masterpieces end up in pieces on the floor, or pulled apart and integrated into strange space/medieval hybrids, I decided to take a different approach: I began to share my LEGOs, and collaborate with my brothers. This had the benefit of giving them shared ownership, so that they were less likely to destroy our creations (at least, until we decided to have an epic battle).

It turns out that learning this as a kid was a big benefit when I began to work at startups. As Molly Graham shares in a wonderful article from the First Round Review, titled Give Away Your LEGOs and Other Commandments for Scaling Startups, having a growth mindset, and adapting to rapidly evolving roles, are key skills to surviving life at startup as it scales.

“At the beginning, as you start to scale, everyone has so many Legos to choose from — they’re doing 10 jobs — and they’re all part of building something important.” Molly Graham, Give Away Your LEGOs.

As designers, another place where we can find ourselves “hoarding our LEGOs” is when we are overly protective of the designer’s toolkit. Many of us spent years honing our craft, and we can be reluctant to give up the helm of our expertise to frameworks like design thinking or design sprints, which are inherently collaborative and don’t work nearly as well if disciplines outside of design aren’t involved.

But aligning cross-functional teams through collaborative work is one of the sometimes overlooked superpowers of the design thinking toolkit. Much like sharing LEGOs with my brothers created a sense of shared ownership, by bringing non-designers into the design process through storyboarding or sketching Crazy 8’s, we create a shared context and are much more likely to succeed at pushing a project forward if stakeholders have been involved from the beginning.

We’re also more likely to help others engage in a divergent thinking process, and be less judgmental when evaluating ideas. As Adam Grant wrote in his book Originals, “Just spending six minutes developing original ideas [makes people] more open to novelty, improving their ability to see the potential in something unusual.”

If there is a thread that ties together all of the ideas here for overcoming the challenges that designers face as companies scale, it’s the power of bringing together interdisciplinary teams into the design process. Whether through user research, creating a product vision, or sharing the designer’s toolkit through collaborative sketching, bringing people traditionally outside the design process, into the design process can help product teams understand the customer, know why they are building products, and ultimately make better products together.

A linoleum-cut project my daughter Phoebe and I worked on a few years ago.

And it not only makes for better products, but it makes for better teams. For those of us who have kids, or nieces or nephews that we’ve worked on creative projects with, this is probably no surprise. Creating something new and sharing it with the world isn’t just fun, but it helps to create a bond that is hard to duplicate. So get out there, and make stuff together.

This post was adapted from a talk I gave at StartCon 2018 in Sydney. Many thanks to my colleague Aarron Walter for providing inspiration and guidance.

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Elijah Woolery

Written by

Director of Design Education @InVisionApp. Lecturer in Product Design @Stanford. Founder of Curious by Design. Father, designer, photographer & entrepreneur.

Design Better

Brought to you by InVision, Design Better provides unprecedented access to the insights that power the world’s best design teams. Learn more at http://designbetter.com.

Elijah Woolery

Written by

Director of Design Education @InVisionApp. Lecturer in Product Design @Stanford. Founder of Curious by Design. Father, designer, photographer & entrepreneur.

Design Better

Brought to you by InVision, Design Better provides unprecedented access to the insights that power the world’s best design teams. Learn more at http://designbetter.com.

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