Every Tuesday through my funemployment, I publish a blog post as part of my self-guided learning program. Last week, I wrote about the importance of rituals and how to find them on the road.

The reality of small design teams

It’s been almost 2 months since I left a promising startup to travel, pursue off-screen interests, and devote time to self-reflection. A big theme threading many reflections lately is work: design in the digital space.

Looking back at my career, one thing most of my jobs have in common is that I’ve worked in small design teams. From design studios to series-B startups, I’ve collaborated with CEOs, product managers and engineers and have executed designs with at most two other designers at a time.

Being part of a small design team in any company is a challenge. And it’s not for everyone. Here are three reality checks that I’ve experienced, and some ideas on how to succeed as a small, in-house design team.

Reality #1: Don’t expect to design 100% of the time

Expect to wear many hats: design advocate, photographer, user researcher, customer support and survey crafter.

As the team and company grows, a designer’s responsibility gradually becomes more focused and specialized. But the process is not without some chaotic, yet highly inventive beginnings. Being the first person on the design team in a company means you will have to establish the discipline of the design practice.

When I came onboard as the second hire at Grand St., the team wanted me to tackle the look-and-feel of the brand, the website and the entire purchase experience. The company had just raised a round of capital, and everything was evolving by the minute. So were everyone’s responsibilities. In between stretches of design time, I responded to customer support emails and edited the copy for product descriptions. Some days, I took my camera and left the office to photograph an upcoming product in the busy streets of Lower Manhattan.

In order to meet the demand of the business, a designer’s role shifts to fill the gap. The design practice that I established at Grand St. was exactly that. Of course, designers produce UX/UI mockups, brand systems and guidelines. But to succeed as a small team in an ever-changing industry, designers need to be adaptive and eager to sign up for new challenges.

But to succeed as a small team in an ever-changing industry, designers need to be adaptive and eager to sign up for new challenges.

After my tour in the consumer ecommerce sphere, I turned to enterprise infrastructure and joined as the design lead at Cockroach Labs. Again, as the first designer, I dedicated perhaps 50 percent of my time to product design, 20 percent to brand, and the remaining 30 percent to business demands. When we needed to grow the team to meet increasing design asks, I spent time reaching out to candidates and meeting peers for coffee. When we needed to benchmark our customer satisfaction with the product, I led the design and distribution of the first product survey. Until we had more HR and product resources, designers at Cockroach Labs wore many hats.

Whether you’ll be the only designer, or the first few to join a small design team, embrace the reality that there will be other challenges in your day-to-day that fall outside of the traditional design discipline. Think of them as a new type of design opportunity, and come up with creative solutions to tackle them.

As the saying goes, “a jack of all trades is a master of none, but oftentimes better than a master of one.”


Reality #2: Communication skills are more important than design skills

Photo by chuttersnap on Unsplash

Wait, what? But I’m a designer. Yes, you are. But we’re all people, including you. It means that we sometimes become so focused on our work and priorities that we fall out of sync with others. In a small design team especially, good communication is key to iterating a product rapidly and to illustrating the value of design.

Designers aren’t efficient when they work in silos. We frequently share work-in-progress with fellow designers, product managers and engineers for feedback and critique. While it’s always tempting to upload mocks to Slack, Jira or GitHub with a “PTAL” (Please take a look) at the end of the day before closing my laptop, I’ve learned to spend an extra 15 minutes and outline what problem the mocks try to solve, how to measure the outcome and what kind of feedback I’m looking for. Communicating my designs through such a framework helps to direct the flood of feedback to be focused and useful, thus speeding up the iteration process.

Aside from communicating with immediate collaborators, designers in small design teams are often tasked to communicate their work across the organisation. When there’s no VP of Design to summarise a quarter’s worth of sweat and pixels, any designer can be put under the spotlight at the company all-hands meeting to share what the design team has accomplished in the past few months. On those occasions, the audience doesn’t tend to be very design-savvy, and cares less about the typeface choice, and more about how well the overall design has worked.

Learning to talk about the design team’s work through business metrics is perhaps one of the most important lessons I’ve learned at Cockroach Labs.

Learning to talk about the design team’s work through business metrics is perhaps one of the most important lessons I’ve learned at Cockroach Labs. Every three months or so, the co-founders meet with the board of investors to discuss business challenges and strategies. As the head of the design department, it was my job to write up what happened in design in the last quarter for the briefing document. I knew very well that our investors weren’t going to scrutinise the look of the database performance dashboard.

Instead, they cared about the number of users, the engagement on the dashboard and how fast you could diagnose a problem in the database. So I made sure that every design improvement I highlighted in the briefing document featured those numbers. And when the numbers weren’t accessible, I presented the design team’s work through the user’s lens: how the colour contrast had improved so our users would notice the error faster; how the tone of the video on the homepage was friendly and trustworthy to developers.

Go the extra mile to structure the request for feedback on the mockups. Put in the time to pull in the numbers and tell a meaningful story of the design improvement. All to make our hard work clear and relevant to our audience. In a small design team, good communication skills go a long way, and benefit everyone in the company.


Reality #3: The path to career growth isn’t so straight-forward

Photo by Jack Anstey on Unsplash

Not having many ladders on the design team means fewer obvious career growth paths.

A flat organisational structure is widely appealing nowadays. But if you report to the CEO or the head of design, how do you advance in your career? As someone who enjoys a small design team, I have mostly reported to the founder or the CEO throughout my career. While my job titles over the years have remained pretty much on the same level, I’ve grown multi-fold, stretching in many areas far beyond what I could have imagined.

True, I have yet to replace any of my bosses. But my exploration of growth opportunities has never stopped, mostly because of two approaches. The first approach is to seek out a mentor. My first job after college was at an eight-person design studio, and the principal and founder quickly became my trusted mentor.

A few months later, I got an offer to work on the first iPad app for The Washington Post. The opportunity was precious, but I was torn. I loved working at the studio, and became close friends with some of my colleagues. So I talked to my mentor about my dilemma one night after work. He patiently listened, and encouraged me to take the offer to go to D.C. “You can always come back,” I remember him saying. I would never be where I am today without taking that offer, and I have my mentor to thank for it.

A good mentor is someone who has your best interest in mind. They may be a family member, a friend, a former colleague, or a current manager. Along the way, I sought mentors both in and outside of the companies I worked at to have a balanced perspective on my challenges and opportunities. They see further than you do, and are invaluable to your growth.

The second approach is to follow your own curiosity and try the things that your peers do that interest you. At Etsy, which was the biggest company I’ve worked at, I partnered with a user researcher for my projects. I was so blown away by her user research process and the insights she was able to gather from the sessions that I begged to try her job for one day.

To my surprise, she was delighted and gave me a quick run-down of how to conduct user interviews. For the next study, I sat in her seat and conducted my first official research interview. Since then, I’ve carried out many more studies on my own, and established user research as its own discipline at Cockroach Labs.

Instead of merely focusing on job title changes, I’ve learned to see the expansion of my skillsets and the deepening of the crafts as tremendous validations of my growth. In a team with a seemingly limited growth ceiling, designers must seek different perspectives from mentors and peers, and take on new challenges that seem worthwhile.

As Steve Jobs once said, “You can’t connect the dots looking forward; you can only connect them looking backwards.” Looking back at the dots that shaped my career, you can summarise them as three lessons:

  1. Embrace wearing many hats.
  2. Develop communication skills.
  3. Carve your own career path.

If you love the idea of not having a typical day-to-day routine, and are excited about learning and growing from trial and error, then being part of a small design team might be the next thrill in your career. Enjoy the journey.


Originally commissioned and published at www.heartinternet.uk on August 15, 2018. Like this story? Share it on Twitter, and follow Back and Forth as I journal through my funemployment every week. I’d love to hear from you.

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