Milestone Reflections and Unsolicited Advice for Designers
Isn’t it our job as humans to be collecting great moments? Photo taken in Reykjavik, Nov, 2024. Mural by Herakut
Ten years ago today I started a new job working for Atlassian.
I was one of two designers working on Bitbucket. This quickly became one designer—me—and then our PMs left the company. Just me and a bunch of excellent engineers for a while. I miss those days. For most of my first couple of years, I was one of 50-ish designers in a company that was only just getting its mind around how to work with design. We grew quickly; it was a wild and rewarding ride. In those ten years, a lot has changed. I’ve grown, the company has grown, and we’ve had a few ups and a few downs.
But Atlassian—the people, the products, our customers—has been the best place I’ve ever worked, I’m eternally grateful for the opportunity and I’m looking forward to many more great years there. Like many reading this, I’m sad and concerned with the direction many tech companies are heading, and while Atlassian isn’t perfect by any means, and some of those concerns apply there as well, I’m mostly proud of the work we’re doing and the way in which we’re doing it.
What follows is a slightly altered reflection I posted on our internal Confluence, primarily for other Atlassian designers. Still, I figured I’d share these thoughts and the unsolicited advice here, too.
Over the holiday break, I took a little time to reflect on my journey as an individual contributor (IC) designer in leadership. The career path for IC designers is something near and dear to my heart. Now that I’m closer to retirement than I am to starting out I wanted to share some thoughts and reflections about what it’s like to be an IC in leadership and some tips and ideas for what’s kept me sane and allowed me to keep at it for so long. I’ve collected many great moments, and while my path has not been typical, along the way I think I’ve learned a lot.
As with most things, your mileage will vary, and you might even disagree with some of these, but I hope they get you thinking.
Ask a lot of questions.
That’s it—that’s my number one piece of advice. It’s a wonderful opportunity not to know something. I like to think my primary responsibility as a designer is to ask questions and consider the answers.
Actively look for problems and opportunities.
Stick your fingers into other people’s pies; just be friendly and helpful about it. Ask to help, ask questions, and dig into the work to find ways to improve it and yourself.
“Share early; share often” is fantastic advice. Do that.
Be proactive and seek feedback whenever you can. Don’t be afraid to show messy work and be sure to include outside perspectives if you can.
Soft skills are more important than technical skills most of the time, and they become more important the longer your career goes.
It’s particularly important to become a good, clear communicator and know how to manage your time.
Get comfortable with ambiguity and being able to shift altitude.
This means learning about product, business, and strategy and being close with your leadership teams while at the same time getting and staying as close to the work as possible. As you move up and your responsibility and influence increase, it’ll be more challenging to stay close to the work, for good reason, but do what you can to remain as close to the work as possible.
Specialist vs generalist? Why not both?
(Yes, I realize that doesn’t make sense. But sometimes things just don’t add up.)
Either can work and often, your work will push you toward one or the other. I’m more of a generalist, but I have the mindset that I can specialize when needed. I like to say my design specialization is design.
If you identify as an introvert like me, you might want to practice being extroverted.
Design is a team sport most of the time, so practice playing as and with a team. I fully believe you can get more comfortable with people if you’re introverted, but it takes practice.
Practice all of the crafts. Color outside of the lines and be flexible.
Become part engineer, lean into product management or research. Exposing yourself to many other skills and work is a good idea, even if you are a specialist. Practice that beginner’s mindset throughout your career.
Learn how to facilitate and bring others into the design process.
Look for opportunities to run workshops or help with design sprints or strategy sessions. Volunteer for these things if they come up; don’t wait to be asked.
Work on your rationale and understand why you’re doing things. Also, examine the rationale of others.
I often think of design as similar to legal practice. You need to research and investigate, have hypotheses to test and learn from, and build and present a case for your ideas and solutions.
Work on your writing.
Written communication will always be a part of what you do. Don’t let AI do too much. People can often tell, even if they don’t say anything and too much reliance on AI prevents some of the personal benefits you get from writing. (AI can be helpful; just don’t let it do all the thinking and phrasing for you.)
Find a way of working that works for you, but don’t be afraid to keep trying other things.
It’s good to mix it up. I find my perfect process is the one that’s working for me at the moment. Sometimes, I write to think; sometimes, I sketch; sometimes, I prototype; sometimes, I explore and make a big mess; sometimes, I’m analytical and dive into research and data. Some people have very solid processes they go to, but even then, in a collaborative environment, you need to be flexible. There is no one right way to do things.
An iterative process is usually best when shipping a great product to customers.
Build relationships with PM and ENG so you can move fast, get better at prototyping, and do enough research so your team can test to learn and get the next iteration over the line. Lean into working this way when you can.
Develop a sense of quality but don’t let unknowns and a quest for perfection slow you down too much.
A Good, better, best approach (something we embrace at Atlassian) is an excellent framework for this. We should build at a level of quality we can be proud of and not rely on our customers to tell us where that bar is.
Practice and growth never stop, but they do get trickier as responsibilities pile up.
It’s terrific to have side projects and hobbies for those times when you don’t have time or energy for “on-the-job” growth. This is doubly important as you naturally move from implementation to influence. Keeping sharp will not only benefit the work, it’ll be more fun.
Practice giving direction and leveraging the work of others.
Even if you stay an IC, you’ll do less and less “hands” work as you move into leadership, and it can be a tricky transition. Not always being the one doing the work is more difficult then you’re probably thinking. I know it was/is very difficult for me. But as many manager-types will tell you, there is a lot of value, and a lot of reward, in facilitating and supporting the work of others. The shift is challenging, but you’ll likely to find that leaning into it will free you up to do more overall, and increase your impact.
Don’t fear mistakes.
Failure isn’t fun. I’ve never been a fan of glorified failure, and it’s not the only way to learn. In my experience, what's essential is being resilient and willing to experiment and take risks. So don’t see out mistakes, but don’t let fear of them hold you back.
Stay humble, helpful, and easy to work with, but protect your energy.
Don’t shy away from pushing back when you need to, and ask questions when things don’t seem right; sometimes, things are not correct, and you might be the only one who sees it. We’re all in this together, so don’t be afraid to be the squeaky wheel. Having said that…
Sometimes, it’s best to dive into the work and see what happens.
We’re not always going to know the best way to do things, and sometimes the best way to move forward is to jump in—together, as a team—and figure it out.
