Coffee Chat Series?
One of my favorite things to do as a design leader is to meet one-on-one with someone in my organization for what I call a “coffee chat.” It may or may not include coffee (sometimes, ice cream is involved; occasionally there is lunch; frequently, there are no beverages at all), but the concept is the same: let’s spend time informally getting to know each other. I want to know what you care about, how you got here, and where you want to go. And I want to support you however I can.
This Coffee Chat Series summarizes the most common topics, questions, and conclusions from the amazing conversations I’ve had over the years with designers at every stage in their careers. Hopefully, it’s a useful guide both for other designers out there and those who work with them.
Are you an Early-Career Designer?
You think of yourself as “new to designing professionally.” Maybe you’re still in school, with an internship or two under your belt. Or, perhaps you graduated in the last 1–2 years and are in the midst of your first or second design job. Or, maybe you’ve decided recently to switch careers.
You don’t yet consider yourself an expert in any aspect of design, whether it’s interfaces or graphics, user experiences or design processes. You may feel you’ve got solid fundamentals and a decent understanding of what good design is, but you can’t yet produce consistently excellent solutions at the level you aspire to, and you believe you are still a good ways off. You look around and can easily enumerate many types of design problems that you haven’t experienced before and would love to cut your teeth on.
You play a support role in bigger product initiatives. In larger teams, you might be paired with a senior or lead designer who is acting as a mentor or creative director. In smaller teams, you may be getting detailed briefs and specific direction or feedback from a CEO or product leader. You don’t typically feel comfortable pushing back on the problem you’re asked to solve or the feedback you receive because you’re mostly in observing and absorbing mode.
You’ve a long and adventurous career ahead. You’re just getting started, and you’re going to leave footprints.
A lot of early-career designers I know don’t assume that they have any superpowers. They figure they’ve got a lot to learn, and not a lot they can contribute. This couldn’t be further from the truth! Pretty much everyone I know raves about working with these people. Why?
Flexibility. As an early-career designer, you come in with practically no bad habits or preconceived notions. You’re not weighed down by the past, so you adapt easily to new tools and processes. Non-existent are the grumblings of, “Well, in my day, we did X or Y and it was so much better…” Within a few years, I’ve seen many people go from n00b to expert designing on some new platform, technology, or cultural trend. And given the rate at which this industry changes — a lot — this kind of flexibility is a huge advantage. When paradigms shift — whether from analog to digital, or web to mobile— you’ll notice that a new generation of pioneers are at the forefront, rather than the established big names from the past. The only way forward is through change, and early career designers are some of the best at adapting.
Curiosity. If you’re new to the field, you’re brimming with a thousand questions. Everything is interesting and novel. You look at problems with a clean slate, which sparks new thoughts and ideas. I can’t tell you the number of times I’ve shown a design proposal and gotten earnest questions from early-career designers like “What problem are you trying to solve?” or “Why does this need four steps?” that made me recheck my assumptions and realize a better solution. Asking for the sake of understanding is powerful; it reminds everyone else to not get lost in the shortcuts that inevitably build up over the course of a long career; it invites us to go back to first principles and reclaim that beginner’s mindset.
Enthusiasm. Just a few weeks ago I chatted with a designer who had taken on mentoring an intern during the summer. I asked her how the experience was. “Simply amazing!” she gushed. “The team loved our intern. Everyone felt so much more energetic with him around!” I hear variants of this story over and over again. As an early-career designer, your genuine and bright-eyed excitement stirs even the most cynical of souls. Problems that more experienced designers have solved half a dozen times already are made to feel fresh again, boosting everyone’s mood. Don’t underestimate how much of a gift this is. Enthusiasm fosters enthusiasm.
Ability to try new things and take risks. At this stage, this much is true: you have far more to gain than to lose. You don’t have a reputation to protect. You haven’t specialized in a particular area of expertise. You don’t have a deep history that people can draw assumptions from. This is the time to take risks! This is the time to raise your hand on the tasks that nobody else wants to do; to join the companies or teams that feel like underdogs; to volunteer for the projects that seem impossible or at the very least, incredibly complicated. This is the time to make like Shakira from Zootopia and “Try Everything.” The worst that can happen is that you get deeper insights into what you don’t like — a valuable learning! The best is that you discover you’re capable of far more than you realized.
Habits for Success
What are the daily practices that have outsized returns for early-career designers? After hundreds of conversations and observations of their career trajectories, this is my short list:
Focus on quantity of work produced. There is a famous study where an instructor for a photojournalism class divided his students into two groups. The first was told that they would be judged solely on quantity — ie, 100 photos submitted gets you an A, 80 gets you a B, etc. The second group was told they only had to produce one photo at the end of the course, and they would be judged solely on how good that one photo was. Guess what? When all was said and done, it turns out that the quantity group did better on both quantity AND quality. In doing the work of producing dozens of photos, they experienced firsthand what made for better composition, lighting, focal length, etc. Meanwhile, the quality group sat around for hours theorizing about what the “perfect” photo was, and then produced one mediocre piece. When designing to solve a problem, try as many different solutions as you can, then scrutinize the pros and cons of each. Trying to “save time” doing something that’s “good enough” isn’t the goal — instead, shore up your fundamentals through a constant stream of high output.
Show your work as often as you can, to as many people as you can for feedback. When I was getting started, I didn’t do this much, and it’s one of my biggest regrets. My excuse was always: “Oh, we already have a weekly team critique — I’ll just show my stuff then.” The truth was, I was embarrassed to ask for feedback, especially on early work that I knew wasn’t totally there. I worried other designers would think less of me if they saw my in-progress work. So I’d sit in my corner and try to perfect my designs before anyone saw them. Unfortunately, by doing this, I missed out on learning faster — I got critique feedback late, I passed up opportunities to get one-on-one advice and coaching, and nobody thought I was particularly proactive. Later on, as a manager, the designers who impressed me the most were those who didn’t let their egos get in the way of their growth, the ones who readily said, Can you take a look at my latest work? I’m struggling with the layout or I’m not sure how to approach this problem and I’d love to talk it through with you first. Ask for honest feedback and listen to it seriously. Iterate based on that feedback. Approach multiple designers you admire for their take on your work. Don’t be discouraged if some days, your work doesn’t meet your (or someone else’s) bar, or you don’t think you’re getting better fast enough. The only way forward is through the work, and through getting more and more perspectives that help you improve.
Work on your growth areas. The conventional wisdom for career growth is to Focus on your strengths. This is good advice in general, but I caution you to not take it seriously at the early career stage. Why? Because right now, investing in your fundamentals — especially shoring up your weaknesses — doesn’t cost you much and will benefit you every day for the rest of your career. If you aren’t strong at visuals, now is not the time to say, “Ah well, I’ll never be a great visual designer anyway, so why bother?” Be wary especially in situations (as in larger companies) where roles tend toward specialization, because you might be tempted to hand off visual work to an expert instead of trying to improve yourself. Even if you have zero aspirations to be an icon expert or a visual systems designer down the road, the more you improve those skills now, the more valuable you will be in every design job down the road. Same goes for other design hard skills — interaction design, motion, product thinking, etc — or soft skills like communication, persuasion, organization, proactivity, or leadership.
Ask questions all the time. As Euripedes said, “Question everything. Learn something. Answer nothing.” Asking questions is the fastest way to learn. Don’t know what an acronym stands for? Ask. Don’t see why your colleague used blue instead of purple on this button? Ask. Can’t really follow the logic behind why your team’s top priority is X instead of Y? Ask. You don’t have to agree with every answer, but you’ll gain a whole lot of context and perspective.
Raise your hand and try everything. Set a goal to try 3 things you haven’t done before every month. They could be new projects, new initiatives, or new practices. If an opportunity comes along and you’re not sure if you’re going to like it or be successful at it, raise your hand. You’ll be better off for the experience, no matter how it goes.
Read books about human culture and psychology. An underrated aspect of becoming a top designer is accumulating a better understanding of human motivation and behavior. Why do people do what they do? How do they process information? When do they behave rationally and irrationally? When does a behavior become habitual, and why? Some books in this category that I’ve found useful: Thinking Fast and Slow; The Design of Everyday Things; Sapiens: A Brief History of Humankind; Atomic Habits: Tiny Changes, Remarkable Results; Made to Stick: Why Some Ideas and Others Die; Predictably Irrational; The Righteous Mind: Why Good People are Divided by Politics and Religion; How to Win Friends and Influence People.
Misconceptions and Obstacles to overcome
In my coffee chats with designers, we’ll often talk about what we wish we knew when we first got started. A few traps stand out again and again as misconceptions that hinder success:
Learning is more important than “proving yourself.” Remember: you have much to gain and very little to lose at this stage. Ask any money manager what the most powerful concept is to build wealth and you’ll hear the same answer over and over again: compound interest. Learning is the compound interest for your career, and the sooner you get started, the richer the rewards will be at the end of five, ten, or twenty years. Resist the temptation to “prove yourself” at the beginning. If you have the choice between banking a surefire success by playing it safe or taking a risk to learn something new, default to the latter. Unlike roles, titles, or rewards, which are fleeting, knowledge and experience gained is permanent. Nobody can ever take that away from you.
Your career is your responsibility, not anyone else’s. If you’re lucky, you will have many folks in your life who will support, encourage and help you in your journey— managers, peer colleagues, mentors, family and friends. But even if you don’t, remember this: your career should matter more to you than to anyone else. So look first to yourself to get where you want to go. You are not entitled to the generosity of others, nor can you control what they choose to do (though I’m always inspired by the warmth and helpfulness of the design community at large). It doesn’t do you any good to blame your environment or your manager if you’re not happy with your progress. You are the captain of the ship of your career, so ask yourself what you need to change.
Designing well is about solving problems for your intended audience, not about coming up with things you personally like. As an early-career designer, I took huge pride in my personal taste. I felt that I had an elevated understanding of aesthetics, of simplicity, and of the journey towards the ideal. But through the course of learning to design for millions, then billions, of people, time and time again I was humbled by the waves of reality. The designs I personally loved best didn’t always have the biggest impact. In fact, often they crashed and burned. I loved minimalism — the more spacious and elegant the interface, the better— but many people out there, especially those newer to the web, appreciate clear, wordy labels over stark icons. Creating excellent work isn’t about me and what I thought was lovely; it’s about meeting our users where they were and empathizing with their needs so we can solve their problems. Resist relying too much on your own assumptions and desires, and seek the truth of what really matters to your audience.
Mentorship starts with asking good questions, not asking for a mentor. It’s natural for early career designers to be excited about getting mentored by folks they look up to. But here’s the thing: 9 times out of 10, getting “mentorship” isn’t like gaining admittance into some sort of program (unless it happens to be structured that way— this is the 1 in 10 case). There’s typically no application process. It’s not a binary thing, like you’re either X’s mentee or you aren’t. In fact, trying to formalize it by asking Can you be my mentor? is awkward, because mentorship should be like any normal relationship — two people who like and enjoy each other’s company want to spend more time together. Refrain from immediately asking someone to spend regular time with you. If they don’t know you well, why would they say yes? Instead, start with genuine questions and low-commitment asks. I’m a huge fan of how you do X — can you share with me some advice for how I can also improve at X? or Can I invite you for a coffee to discuss X? If that goes well, then you can make another ask or request to make it a more regular occurrence.
Reflection Questions to Ask Yourself
The best thing you can do for your career is not to listen to what someone else has to say (this article included), but to get in the habit of regularly asking yourself deep questions. You’re the only one who knows your true heart and where you want your career to go, so keep these questions in mind:
Which qualities of people around me do I admire, and how can I learn from them? Seeing is believing. If a colleague does something that leaves you thinking, Damn, I wish I could do that— maybe its the simplicity and elegance of their design work; maybe its their attention to detail; maybe its the compelling way they make arguments— count your lucky stars that you get to see them work that magic and that you have the opportunity to learn from them. Admiration doesn’t have to be all or nothing. You can appreciate a particular skill or trait without admiring everything about a person. Make a list of those qualities, and then ask yourself how you might get better at them. Can you ask that person to give you feedback? Can you request that they deconstruct their process? Can you make notes of their specific tips and tricks?
How can I find out more about my likes and dislikes? It’s perfectly natural to respond to a question like “What am I meant to do with my life?” with I have no f-ing clue right now. You can’t rush discovering the answer; it’ll emerge in its own time, through first-hand experience with the kind of work that gives you the greatest satisfaction. But what you can do is put yourself in situations where you’re constantly testing new scenarios and learning about yourself in the process. These experiments might not all be successful, but think of Thomas Edison, who said, “Just because something doesn’t do what you planned it to do doesn’t mean it’s useless.” You may try things and learn that you despise certain tasks but love others — this is what self-discovery looks like. if you don’t get out of your comfort zone, it will take you much, much longer to find your true calling.
What things gives me energy, and what sucks away my energy? This is is a simple reflection question to contemplate at the end of a month, quarter or year that is a baby step towards answering the much bigger existential question of “What am I meant to do with my life?” Simply observe which activities give you energy and feel rewarding, versus what make you feel heavy and discouraged. Don’t react or change your actions based on a particular month or quarter’s answer; narrowing your area of opportunity too quickly is limiting. Instead, note them and jot them down. What’s valuable is understanding the larger trends or patterns over the years — I am energized by people who take their responsibilities seriously and share my optimism in the future — not specific examples like I don’t enjoy working with Taylor.
What are my unique strengths and growth areas? Like the question above, this is an important reflection question to understand yourself better. Make note of your strengths, but don’t ignore your weaknesses — instead, focus on improving them to establish a better foundation for the future. Continue to broaden your field of experiences, but periodically take stock of what things come naturally to you, and what you struggle more with.
Next in the series: Making Intentional Choices as as Experienced Designer.
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