Photo by Adriaan Goossens (https://flic.kr/p/cLDnjA)

Lessons I’ve learned from leading designers

There is a scene in my head that I have run into many times over the years. A desk littered with sketches. Empty coffee mugs and coffee ring stains decorating a desktop like layers of weathered graffiti. A designer with a panicked look in her eyes clenching her mouse and clicking away furiously as artboards sweep across the screen so quickly that it looks like static from a 1960's TV set.

“I‘ve tried everything, I have dozens of concepts here and nothing is working right.” There’s a glimmer of hope in her eyes that you will swoop in as the creative director and say just the right thing that will lead to a brilliant solution, but being able to break free from a design block is part of the process of maturing as a designer. My job as a lead and creative director is not to dole out all the answers to problems, but find ways to guide individuals to a great solution on their own. In this way, they can grow and build confidence in their skills.

Every designer is different, naturally, because every person is different. I have to figure out with each working relationship what inspires, motivates or resonates with that person so that I can gauge a leadership style that will elevate their growth. Over the years, however, I have found patterns in the types of problems I’ve helped designers work through. I‘ve learned a few tips and tricks along the way to help guide them through these scenarios. I will go into four of these in more detail.


1 The information hoarder scenario: This scenario is when a designer wants to be a nomadic gatherer of information, trekking around to compile as much knowledge as possible before putting pen to paper. This can include but is not limited to: research, data usage, information on competitors, different technologies and all related feature experiments the team has tried before. The trouble is, product design isn’t a world where you are going to know everything before you can start sketching. One has to figure out the balance of what knowledge is essential to know before pushing pixels versus what knowledge will remain in flux. Digital products are living, breathing ecosystems that change constantly from user’s behavior, and when features are being designed, it’s inevitable we already know something more to add to the equation that could solve the problem. This process can cause churn and constant tweaking, paralyzing work from going out the door.

The guidance I try to give in this scenario is to help the designer break through his or her fears. I had a small project assigned out to a junior on designing a simple checklist for an online store. He wanted to spend a week doing competitive analysis to see everything that everyone else had done so he could be inspired and do something completely new. Now, there was no way I could have him spending an entire week on something so straightforward on an agency budget, so I challenged him to start sketching immediately. I asked him to do 5 different quick hand sketches of how the checklist could come to life. He showed them to me, then I told him to spend the rest of the day seeing what the rest of the world had to offer on this topic. The next day he came back super excited that he had discovered patterns (best practices) for checklists and that some of his concepts matched those patterns, but some of them were wildly different. In that exercise, he validated his work and built his confidence that he had original ideas of his own.


2 The deconstructor scenario: This scenario is one where a designer takes a problem, breaks it into a million pieces, puts it through a spin cycle and then explores every avenue a solution can go down. The fear is that an idea could be missed if not approached from every possible angle.

I do love the deconstructor scenario. Often times, some of the best design solutions I have seen come out of the situation where designers aren’t afraid to approach the problem from a completely whacky perspective. Sometimes, however, the fear of not exploring a solution, can send the designer into doubt. I have seen designers leave a crit with 20 stickies in their hands of notes, knowing that each of those stickies is a new idea or direction they want to pursue. Huzzah for that initiative! In the world of product design, you aren’t often left with a ton of time to explore all of those solutions and one has to learn how to know what is worth exploring and what is not.

One common equation of concepts I ask to see is one obvious solution, one crazy solution and one that sits somewhere in between.

In this situation, the designer needs help culling down the options and ways to prioritize their recommendations and decisions. I actually expect and love that designers on my team have sketch files that look like one side of a glass skyscaper, with beautiful sets of squares all stacked up neatly one on top of the other stretching into the clouds. What I expect to review, however, is very different. When I sit down next to a designer to see work throughout the process, or in a crit review, I expect to see no more than 2–3 solid directions. This goes for many situations, from branding to initial wireframing work. I do not want to see a whole wall of many different directions, because that means to me a designer has not thought through the concepts enough to determine if they are really viable solutions. One common equation of concepts I ask to see is one obvious solution, one crazy solution and one that sits somewhere in between. From there, I ask how she came to decide upon these three. What results is a set of guidelines that the designer used to decide what solution was right. I encourage designers to find guardrails that work for them. Over time, I start to see that the sketch files tend to dwindle from a skyscraper set-up to a townhouse as a designer matures and can make the decisions much more quickly upfront in the process.


3 The systems breaker scenario: In this situation, the designs are usually really good executions, but tend to solve problems in silos as opposed to seeing how a solution can be part of a larger whole. “That alert banner style we have for this page just doesn’t fit in with what I want to create, so I changed the color and alignment.” The alert banner will look beautiful in the page, but will not be communicating a larger system-wide message within the product.

I find guiding in this scenario challenging, because often I can identify with the solution and recognize it might be better in that flow, but know that as a whole, it is not the right way to approach the problem. What I try to do is give guidance on finding other ways to creatively solve the problem. For example, is an alert banner the only option that can be utilized? Are there other ways to communicate the message to our users? Are there other patterns we can explore? Sometimes, questioning in this way can drum up a good answer. Other times, we find that a toolkit is limiting and may need to be expanded, so that’s what you should do. I do believe that adding or changing something in a toolkit should be a bloody fight, knowing that all options were explored and that the system’s integrity is staying in place.


4 The innovator scenario: Currently, I am privileged to work with a group of designers who really push the limits and inspire me. I get hit by the humble brick often with this talented group of people, who school me as often as I school them. What do you do in a situation with designers who don’t really need guidance? They are coming up with brilliant ideas, doing all the right things and have proven to be extremely successful. I have to reach deep down into some unconventional methods with these folks when they encounter a rare block.

Go find a quiet spot and write a story about the problem you are trying to solve…the interfaces are just a conversation the user is having with our product

I remember an example of one designer this year, probably one of the best I’ve ever worked with, who came to me reluctantly to say she had hit a wall and just couldn’t get out of a block she was having with a particular flow in the product. I recommended for her to get out of Sketch and leave it behind for a while. The state she was in, it was only going to frustrate her more to keep churning over her files. I suggested she go find a quiet spot and write a story about the problem she was trying to solve. We are designing for people, and the interfaces are just a conversation the user is having with our product. If the user was to converse with the product, what would she want the dialogue to be? The designer spent the afternoon writing and found her way out of the challenge she was having into a great solution. By shifting gears and stepping back higher in the process, she was able to create a different approach to the problem, one she and I were really happy with.

I often ask designers to look to other industries and creative skills to help them solve their problems. How would a writer tell this story? How would a particular fashion designer put together this color palette? This is where I find the joy and drive in my own work today. I seek to find inspiration in unusual places to fuel creative solutions.


As a leader, I’m rewarded when I can encourage and cheer on a designer’s superpowers. It builds confidence and a sense of autonomy that is to be celebrated. It’s just as heartfelt when I can guide a designer to reach deep, push boundaries that are uncomfortable and expand into the unknown. Draw knowledge from your own experience. Push your designers to think differently.

Read more from the Airbnb design team at Airbnb.design

Published in #SWLH (Startups, Wanderlust, and Life Hacking)

Show your support

Clapping shows how much you appreciated Amber Cartwright’s story.