Finding a buddy when you’re a team of one

Originally posted Jul 11, 2023 • More resources on cross-functional relationships

I’ve been working with the rad team at Fly.io for the past few months as a fractional VPE, mainly focusing on management-y and culture stuff as the team grows.

One of the things I really dig about Fly.io’s company culture is how teammates use their internal forum for sharing questions about work, project progress updates, oncall recaps, and other stuff that I’ve traditionally seen live (and die) in email inboxes. I’m finding that the internal forum helps keep conversations going async (and out of Slack, which can be super lossy for folks in different timezones) and a little bit more evergreen.

I wrote a post on their internal forum last month about a topic that had been consistently coming up in 1:1s I had with folks: how lonely it can be if you’re working as a team of one. I realized that this post might be helpful to folks outside of Fly.io, too, so with their permission, here’s a lightly edited version :)

tl;dr: if you are a “team of one” and ever feel stuck/isolated, it’s totally normal (and encouraged) to lean on other folks here for help!

I’ve been chatting with a few different people about what it feels like to be a “team of one” at Fly.io. A “team of one” can mean anything from “I’m working solo on a project,” or “I am the only person tasked with thinking about this entire product area,” or “I’m venturing into a new area of the business and am gonna test to see if we want to build a team around this thing.” For many folks, this level of autonomy is fun and interesting!

ALSO, despite it being fun and interesting, being a team of one can—at times—be lonely or hard.

I am all about leaning on different types of people at work (and outside of work) as you tackle challenges, grow your skills, etc. (Here’s a whole metaphor for building a “Voltron”/crew of support!) But sometimes it can feel really tricky to find those people—and even if you know you can lean on somebody, it’s hard to know how.

Examples of how to lean on/get support from other folks within the company

In case it’s helpful to have examples (or inspiration, ha!), here’s a non-exhaustive list of the different ways you might be able to lean on somebody else for support, when you’re a team of one:

• Coaching! I’m biased; I had to put this one first in this unordered list. ;) Finding an external coach can be useful, but there are also plenty of people at Fly who are trying to practice their coaching skills! This means they’d ask you lots of open questions to help you figure out what you want to do going forward. You can think of it like dedicated introspection time, facilitated by another person.

• Feedback! People here are also trying to hone their feedback-delivering skills. Asking someone to give you feedback on your implementation can feel micromanage-y, so instead, you can ask for feedback on a different aspect of your project! For example, ask somebody what risks they’d consider if they were working on your project. Or ask them what open questions they still have about your project based on your previous updates. Asking for feedback on different parts of how the project is going can be really helpful to get some brainstorming happening.

• Rubber ducking! Sometimes, you just need to type out your plan, current thinking on your approach, order of operations, etc. to work out where you’re stuck. You can ask somebody just to be a rubber duck while you process with your typing words or mouth words!

• Pinging when you’re stuck! While it feels obvious to ping someone when you’re stuck, it can weirdly be challenging to do this when you’re a team of one. Consider identifying a person in advance who you can holler at when you’re stuck, and ask them the best way for you to notify them that you’re stuck! Crafting this minimal pre-work agreement can make it far easier to reach out when the time comes to get unstuck. When you ping them, you can tell them what kind of help you might be looking for: rubber ducking, feedback, coaching, etc. Or they can ask you ;)

• Ghostwrite messages! For some folks, the hardest part about being a team of one is the communication work. They’ll grind their gears trying to write stuff, and either give up on it or go quiet for a really long time. If this is you, find someone who can help you carry some of the writing load! The process of sharing your current status, what you’ve shipped, what’s important for people to know, etc. means you’re STILL doing the important thinking parts that updates require. Sometimes, offloading the writing itself is all that’s needed.

• High fives! It feels really good to see people using your stuff, but sometimes, what you REALLY need is a high five from somebody who knows the work it took to get something shipped. See if you can find someone to help you celebrate when the whole thing is wrapped up. Even if that just means some tada emojis in a Slack DM ;)

Finding a buddy

Now, how do you find a buddy to help you with this stuff? Some brainstorm-y ideas:

• Is there a senior-ish person at or outside your company who you’ve worked with before, and would like to be a high five buddy, coaching buddy, feedback buddy, or whatever it is you’re looking for?
• Could the Slack Donut app help you find someone new to chat with within the company?
• Should there be a #buddy-system Slack channel where folks can go to ask for a buddy?

If you’re wrestling with this feeling at work, I highly recommend you find a way to talk about it with your colleagues. Even just sharing this post could be helpful to kick off the conversation! I hope this can help you develop easier/more obvious support for folks who are feeling isolated with their work.