A designer’s 5 lessons from 5 years growing a startup

Everyone experiences failure at one point — but no one really teaches you how to deal with it. I’ve asked about failure many times many ways. Seeking advice on how to navigate my own failures or just looking for a shoulder to lean on.

I was listening to Brene Brown’s Dare to Lead podcast at breakfast one morning and a phrase stopped me mid-chew. It was a quote from The Rise, Dr. Sarah Lewis’ book on creativity and the gift of failure.

The word failure is imperfect. Once we begin to transform it, it ceases to be that any longer. The term is always slipping off the edges of our vision, not simply because it’s hard to see without wincing, but because once we are ready to talk about it, we often call the event something else, a learning experience, a trial, a reinvention, no longer the static concept of failure.”

I played it again. Wow 🤯

I finally grasped the nature of failure. It doesn’t stay failure forever. It transforms into an experience, a learning moment.

As a product designer I helped grow Drift, a sales and marketing company, for 5 years. From 7 employees to 400+, from one office to four. Along the way, I’ve tweeted tiny snapshots to help cement my f̶a̶i̶l̶u̶r̶e̶s learnings into memory. These are my 5 biggest lessons from each year I spent at Drift while navigating the Product-Market Fit and the Growth stage.

Year 1: Innovate don’t re-invent

I learned this one the hard way. Like the naive recent graduate I was, I was eager to show the world what I could do with shiny new solutions from scratch… in an industry I was brand new in. I had an ego and didn’t realize it. But nothing I created made sense. Our users were getting caught up in complex UX flows and made-up terminology.

Finding product-market fit isn’t only about standing out from the crowd. It’s also about being easy to adopt. It takes a lot of effort for users to learn a new product, so you need to lean on patterns they’re already familiar with to make it easier to get started. Your job as a designer is to reduce the cognitive load of learning new things.

But how can you stand out this way? Take the common patterns that work well and make the last 10% remarkably yours.

What you can do about it 🌱
I learned the innovate don’t re-invent framework from our CEO, David Cancel.

• Find a role model — one that solves the same problem you’re solving, or a similar one. The role model doesn’t need to be in the same industry (although that’s preferred). But for example, onboarding is a problem solved across all industries.
• Stick to that one role model. Don’t combine products together because you’ll end up frankensteining two different patterns and systems together. No bueno.

Year 2: Speed is your competitive advantage

I believe speed is directly correlated to your rate of learning. The faster you go, the more opportunities you have to learn from your wins and losses. When trying to find PMF, you need to figure out what sticks with your users and what doesn’t — quickly.

Designing heads down for too long — even just a couple of days — is harmful in the long run. To “emerge” and have a design be technically risky, unfeasible, or worse it doesn’t solve the customer problem at all… are risks that slow your team down.

What you can do about it 🌱
Constant communication is key to moving fast. At the beginning of a project — your job as a designer is to start a conversation around a possible visual solution. And surprise! You don’t need a fully polished design to do it.

• Start with broad low-fidelity designs to get the concept across, ignoring details like color and component usage. Focus instead on the user flow to complete the task. Using pencil sketches or text is enough to communicate ideas with your team to start the conversation.
• Next, get to a point where it’s testable. It should have just enough detail so you can start learning from users. Then take those learnings and dive into even smaller details (color, spacing, typography).

And if you’re stuck in an endless loop and unable to figure out a solution that makes sense to you? Just test it. Remember: you are not the customer. You need their point of view. Get eyes on it, really.

Note: This lesson doesn’t apply to the stage Drift is at anymore. Shipping fast was our advantage at the time because we were a small company and new in the market. We didn’t have many customers so our mistakes had a smaller impact.

Year 3: As the team grows, figure out how to scale yourself

Going from a small team of 2 designers to 5, I was used to having a hand in all parts of the product process. From problem discovery, conceptual research, designing, and user testing, I was so eager to be a part of everything. But as our team grew and the problems we solved became more complex — I wasn’t able to keep up. I spent too much time in one area which meant sacrificing time in another.

I became a blocker and slowed the team down. After some painful moments with my ego and self-worth (bonus personal lesson: your productivity is not your worth), I realized I needed to be ruthless with my time, and outsource what I could. There’s no shame in asking for help when you need it.

Molly Graham gave an amazing talk at Drift on giving away your legos. You need to give away all or part of your job so you can be free to work on other things. In turn, you’ll grow in ways you couldn’t before.

What you can do about it 🌱
Identify and remove yourself from parts of the process you don’t need to be involved in. This can be as big as handing over an entire team, or as small as handing over tiny process.

• Share your own approach to ease the transition before you chuck your legos. I like to put together “lego toss documents”. They include links to design files, background research, team dynamics, and any rituals I owned.
• Automate yourself where possible. I was posting weekly Slack reminders coordinating our team’s Design Lab ritual and automated it with Zapier.

Year 4: Team changes are hard

As companies grow, new teams are created and spun up meaning strong relationships need to be built quickly. Richard Banfield gave an awesome talk at Drift about high-performing teams and introduced the idea of creating psychologically safe spaces where teammates feel comfortable to experiment and play. To create that space, teams need an underlying layer of trust and vulnerability.

I personally think this is the most difficult type of change because it involves people. Especially as someone who struggles with vulnerability and letting down walls, I needed to get outside my comfort zone and be intentional about building strong relationships.

What you can do about it 🌱
I’ve learned that most problems stem from miscommunication. And in order for teams to have strong communication — they need to trust each other. With new teammates, it’s so important to build trusting relationships quickly. Here’s what I’ve picked up.

• Put in the effort. I always ask two questions on my first 1–1’s with new teammates to get to know them and their working style. What’s your biggest pet peeve a designer does? What’s your favorite part about working with a designer? This invites the other person to ask you these same questions, letting you both set your expectations.
• Provide clear feedback when you notice behavior you don’t expect. Or encourage new behavior you want to see. For instance — if there’s a lull in communication with a new teammate I’d send over a quick Slack and see if they had any questions on the design.
• Lean into vulnerability. When things aren’t going smoothly, acknowledge it and brainstorm with your teammates how to improve it together for next time. Make sure your teammates know it’s okay to make mistakes and that you’ll have their back no matter what.
• Celebrate your wins! 🎉

Year 5: Break problems down into small chunks

⬛️ ⬛️ ⬛️ ⬛️ ⬛️ ⬛️ ⬛️ ⬛️ ⬛️ ⬛️ ⬛️ ⬛️ ⬛️ ⬛️ ⬛️ ⬛️ ⬛️ ⬛️ ⬛️ ⬛️ ⬛️ ⬛️ ⬛️ ⬛️ ⬛️
No tweet this year! I was quiet during 2020 making space for others

As Drift grew, the stories we solved became more complex. Instead of spanning a couple of weeks, they began to span multiple quarters. It was a big shift in the way we thought about, planned for, and built product.

Big, ambiguous stories can be paralyzing -especially when you don’t have a plan. It’s easy to get overwhelmed by the “what-if’s” and I’ve found myself in circular conversations, multiple times. It doesn’t feel great.

What you can do about it 🌱
Make a plan! Break the work down in a way that makes sense for you and your team. Start with a birds-eye view to identify what’s missing or unnecessary, and then fill out the details. Milestones, Chapters, Ships, JTBDs whatever. Just break it down. Why?

• The problem becomes less daunting. Instead of a big scary unknown, you’ll be able to see a solution in clear, manageable pieces.
• You can stay focused on one task at a time. You can put away the “what-if’s” knowing you have a place for it later on.
• It helps with time-management, cross-team coordination, and setting expectations with stakeholders. Being able to look at each piece individually lets you get a sense of what’s easy/hard, and where your team needs outside help.

Back to f̶a̶i̶l̶u̶r̶e̶ learning moments

These 5 lessons were born from moments of failure, but reflecting back I’ve transformed them into learnings. There was another gem of a quote from Dr. Sarah Lewis’ book. She wrote:

Mastery is also not the same as success — an event-based victory based on a peak point, a punctuated moment in time. Mastery is not merely a commitment to a goal, but to a curved line, constant pursuit.”

Believe it or not, mastery and success aren’t the same. The difference is whether you continue past your success and failure. I love the imagery of committing to a curved line because it shows that the path isn’t clear cut. There are successes and failures sprinkled throughout 💫

It’s scary as hell — no one likes failing. But if we learn to accept failure’s role in our journies, then we can embrace it and use it as fuel to propel us forward.

What’s one of the biggest f̶a̶i̶l̶u̶r̶e̶s learning moments from your own career journey? Let me know! Find me on Twitter @dandyamandy

2020 BONUS lesson: How to WFH on a rainy day

Brown, B. (Host). (2020, November 23). Brené with Dr. Sarah Lewis on The Rise, the Creative Process and the Difference Between Mastery and Success. [Audio podcast episode]. In Dare to Lead with Brené Brown. Parcast Network. https://brenebrown.com/podcast/brene-with-dr-sarah-lewis-on-the-rise-the-creative-process-and-the-difference-between-mastery-and-success/