30 January 2025
Podcast edition! I was delighted to be able to join Brian and Erin on DevRel(ish) yesterday to talk about remote work. I was surprised by how much I enjoyed the live format and they were exceptional hosts. It almost feels like I enjoyed the experience a bit too much, and the hour flew by. I found myself reflecting on the conversation and adding up all the extra things I wish I had said. Instead of spiraling over this, I thought it could be productive to put them in a post.
The conversation was largely focused on human connection—I find that nothing matters more than this, both professionally and personally. For me, my greatest issue with working remotely is that it can be incredibly lonely. Everyone seems obsessed with streamlining for “efficiency” and the need to connect with those around us is regarded as unnecessary fluff. Further, the larger world around us is creating more disconnect and divisiveness amongst us.
I lost count of how many meetings I’ve attended led by people that just jump right into the topic at hand. I don’t want to work with these people because I don’t know them. I’ve been in meetings with a great turn out in numbers, yet they were all very isolating and forgettable. I have trouble focusing as I am being talked at by a stranger. I retreat and put my head down just to get through tasks—all deliverables that would be made better through stronger relationships and proper dialogue. This is what happens when we downplay the importance of connection and mistake work-only spaces as more impactful and somehow smarter.
When we are lonely and feel disconnected from our colleagues, clients, and friends, we struggle to perform. Also, to be frank, most people want to work with people they like and have a good rapport with above all else. While it feels viscerally strange to have to advocate for connection and the fight against loneliness, I’ve learned that it is completely necessary. Especially in the remote context, we are quick to discard these basic human needs. Regardless of title and role, relationships are the foundation of our work, our experiences, and our overall quality of life.
So, I’ve spent a lot of time both on the podcast, within this post, within other posts, on social media, and in-person talking endlessly about this. But I’m passionate about it, have experienced how critical it is, and can see where this current war on remote working is headed—we cannot lose sight of prioritizing connection in a world that is actively trying to prevent it. Isolation doesn’t inherently have to be a part of this lifestyle and a healthy remote work culture is possible, but it takes deliberate effort. The big shift for me was when I realized that I was the one that had to figure this stuff out.
A question was posted during the show around how we as individuals can foster these connections outside of looking for employers to do so. I really loved this and wanted to spend a bit more time responding here.
While I think there is an important role for employers to play in fostering healthy remote work cultures, so much of the work that has to be done to connect with people over a screen is on us as individuals. Additionally, some of us don’t have formal employers. I wrote about this recently in another blog post, and feel it can ultimately be summarized by understanding our own responsibility in conversing with other people. It’s a give and take. There are risks. Bravery is required, and everyone is best served when we wholeheartedly consider the experience that others have when talking to us and we give these opportunities the planning, attention, and care they deserve.
Some of the work here looks like: asking people about themselves and listening with sincere interest, allowing for vulnerability, sharing parts of your life and topics of interest, giving advice as much as it is sought, closely following any community rules when applicable, celebrating the wins of others, showing gratitude, thoughtfully communicating to ensure understanding, interjecting personality into writing, being helpful and involved when possible, turning cameras on for video calls, actively taking part in and starting discourse.
As a final note here I am reminded of a quote from The Art of Gathering, which is: “Don’t be a chill host”. While referring to hosting gatherings and events, I think it serves us well to regard ourselves as hosts of each interaction we have with others.
If I had to call out a single hack to making better connections on and offline, it would be to ask better questions. Asking questions is an art but also teachable with insight and practice. I credit my time as a designer a lot here in understanding how important the right questions are, including their delivery and intentions. I’ve also read some incredible books on the topic that I reference often, such as, Ask Powerful Questions, The Book of Beautiful Questions, and The Fine Art of Small Talk.
I keep a post-it on my monitor that says “How and What, not Why” as a reminder of how to start more insightful questions. Leading with how and what opens dialogue up to stories and continued interaction, while why questions can create defensiveness and end an interaction before it has a chance to begin.
These books include specific examples of questions based on context, so while I will include a few here, it’s ultimately about actively listening and asking open-ended questions where you are actually interested in the response and allows the person to feel seen and heard.
I think it’s easy to see how these will take you further than “How’s it going?”.
Increasingly personalize questions as you uncover more details about someone and remember these details for later. I also keep a long living document of Wiggle Work daily discussion prompts here that could prove helpful for teams and communities.
Wiggle Work is a Discord community I started in 2023 during an especially isolating time. In an effort to contrast the overly serious spaces we are immersed in each day, I tend to get too excited to talk about how fun and silly this space is. And while that’s true, I also don’t want to downplay its impact and significance. This is a space where I am genuinely eager to hang out all day. I count Wigglers as friends. They are so smart, impressive, interesting, curious, clever, caring, and hilarious. It’s such a good bunch and I’m lucky and grateful to have them around.
You can share your failures here along with your wins, and someone is going to reassure you and has likely had a similar experience. These folks are quick to help each other, get and give advice, and be a source of comfort and consistency in uncertain times.
It’s the water cooler connection we have all been missing since being remote. It’s a place for work but also a place to be down-to-earth and talk about hobbies and books. It’s a place where lasting, invaluable connections happen without all the overly formal phoniness of traditional networking spaces.
I would have liked my parting words to have been: please join us, we can’t wait to get to know you. The application is quick and painless but helps me best track members and make sure everyone is on board with our code of conduct and community expectations. I’ve put a lot of thought into crafting a warm, welcoming, and sincere atmosphere here—I truly hope you are able to feel that when you arrive.
Thank you Brian and Erin!
