What It’s Like Working Remotely on Stack Overflow’s Design Team
A lightly edited transcript of an AMA (Ask Me Anything) I did in the Remotive Slack community.
Could you tell us a bit about yourself and your professional background?
I’m a designer at Stack Overflow, where I create better workflows for over 50 million developers. Before that, I designed digital products in the medical industry. Since 2001, I’ve been trying to create work that’s cool enough to show my friends and honest enough to show my parents. When not in front of a screen, I enjoy exploring northern New Jersey with my wife and two kids. I enjoy playing + watching hockey and soccer, and always love a good episode of The Simpsons or Black Mirror.
What does a Principal Product Designer’s work day look like?
Product designers at Stack Overflow are involved in almost every aspect of the product process. We’re encouraged to pitch things on the company roadmap, lead the design discovery phase of projects (user search, prototyping, etc.), create artwork for interface design and UX flows, and guide implementation of our designs (either working with engineers or contributing code directly).
I was promoted from a Senior Designer to a Principal Designer in July, so now I have additional responsibilities of evangelization within the company, communicating across teams, and taking a more active role in quality assurance.
In a typical day I have ~2 hours of meetings, and the rest is spent writing (Google Docs), designing (Figma), or coding (Sublime / VS Code). I’m in contact with my coworkers throughout the day via email and chat. I’m trying to get better at batching my meetings together and temporarily closing chat and email to focus on deep work.
How remote friendly is Stack Overflow? Countries and % of total company size.
We are very remote friendly, but not truly worldwide. We’re in about 15 countries, spanning from Slovenia to California. We have one fella in Russia at the moment, but it’s not his permanent location. And we have a few in Australia, but most folks are between CET and PST time zones.
Here’s a graph that shows a breakdown, but note that most of the Sales team is in NYC so it really skews this graph. Our product team is mostly remote / distributed.
How does Stack Overflow organize work with people in different timezones? Do people in the same timezone work on the same product or teams?
We have most of our meeting in the middle of the day EST. Not quite quitting time for Europe and not terribly early for west coast of North America. We do our best not to ask folks to attend meetings outside of normal work hours, but it does happen from time to time. As sometime in EST, the biggest problem I have is protecting my calendar so I have enough time to eat lunch. First world problem, I know!
Regarding team organization, it varies. Some teams operate well when everyone’s working at the same time, while other prefer to work more asynchronously and hand off work as folks start and end their days.
Our whole company uses the Google Suite, and thankfully Google Calendar does a great job of handling timezones and letting folks mark their working hours.
Could you talk about the job search process that led you to land a job with Stack Overflow? Dos and don’ts? What tools helped you, which didn’t?
When I joined Stack Overflow, I wasn’t looking for a remote job specifically. I had a bad couple of weeks at my office job and decided to “see what was out there” job-wise. Since I had a good job, I had the privilege of job-hunting at my own pace.
I saw the ad for a product design role at Stack Overflow on dribbble’s job board. I applied by designing and sending a HTML email as my cover letter, which helped me stand out and helped get my foot in the door. From there, the interview process was relatively typical and ended with an offer that I accepted.
When job hunting, I focused on quality over quantity (again, since I had the privilege of going at my own pace). I used only three or four job search tools that had a good signal-to-noise ratio for the roles I was interested in. I researched every company I considered and only applied to a handful of jobs.
On the subject of job boards, lately I’ve been impressed with We Work Remotely, Just Remote, and Remotive (and I’m not just saying that!). Lots of good design and tech roles. I’d ❤️ recommendations y’all on other places to look!
What makes you interested in a candidate for a new position? What makes you dismiss them from the start? Any interview tips?
When I’m interviewing, I look for folks who are…
- Collaborative. Great work is rarely produced by a lone genius who prefers working in isolation.
- Are stubborn on the vision but flexible on the details. If you want to produce high quality design you need develop a strong opinion, but one shaped by that of many others.
- Dependable. Remote work requires a lot of discipline.
- Good writers. Writing forces us to understand what we believe.
- Confident but humble.
A tip: treat a remote interview just as you’d treat any other interview. Do your research, show up on time, and be yourself. Don’t get hung up on the “remote” aspect of a potential gig.
What are your best tips/practices for onboarding new remote employees?
Plan out their first month in advance. It helps set expectations about what a new hire should be learning and when.
When I joined Stack Overflow, the team didn’t have a codified onboarding process and I was thrown into the deep end. Stack Overflow is pretty transparent with information and we use a lot of apps to communicate… and I was given access to everything on day one. Here’s what that looked like:
There were rabbit holes at every turn. A Trello card that links to a Google Doc that references another Google Doc that links to a saved chat transcript that discusses an Invision prototype. Everything has comments. Every comment has replies. Every screen name links to a co-worker’s profile. I followed the breadcrumbs in an effort to piece together who was who, what they’re talking about, and what time zone people are in.
Without much structure, it was easy to get lost in a sea of information. I often wasn’t sure exactly what I should have been doing those first few weeks and felt like I should be accomplishing more.
I wrote about it for anyone interested.
We now have an onboarding process that spans a new hire’s first month, broken out by week. Everyone now knows what’s expected from a new hire after their first week, after their second, and so on. A new hire can skip ahead if they want, but expectations are clear and what should be happening at any give point.
Whatever shape it takes, it helps to have an onboarding process beyond those first few days so that everyone (the new hire AND the existing team) knows what is expected each week and what to tackle next.
What has been the biggest impact that working remotely has made in your life?
- Ability to be around my family. Among other things, being able to see my two children grow up is invaluable.
- Ability to live where I want. Without being shackled to an urban area, we’re able to afford a nice house in a great school district that’s close (but not too close) to family and friends.
- Of course the flexibility is nice. Running an errand mid-day, not fighting through traffic or a snowstorm, eating better meals, etc.
What is your current office setup? Could you share it with us?
I wrote a blog post about just that. TL;DR: I usually work from my home office, which looks like this:
What happens to the internet when Stack Overflow goes down?
😂 Maybe some folks here can tell me what it’s like outside the company. I see many of the same jokes / memes as when Slack or Facebook go down.
We do have a few outages a year, but they’re mostly short-lived. They usually happen when most of us are working, so folks are always around to work on it immediately. We had an outage earlier this week: our team was able to bring the site back up in read-only mode after a few minutes, and back fully in half an hour.
Also published at https://blog.prototypr.io/what-its-like-working-remotely-on-stack-overflow-s-product-design-team-c3a4034c265e