Collaboration
Back in high school, I built robots with a group of exactly the sort of teenagers you’d expect to find in a robotics club. I was physically weaker than most of my peers, so I had to use tools and leverage to complete routine tasks that others could do with their bare hands. This gave me more practice with those tools than others were getting. When the tasks scaled up in difficulty – a stuck bolt turning out to be very stuck, a thicker sheet of metal turning out to be unusually reluctant to bend – my tool use tended to scale up quickly thanks to my constant practice with it, whereas peers who’d been brute forcing the task before would face the initial learning curve of the tool at that moment.
I think I’m doing a similar thing with collaboration. I have to try really hard to keep in touch with people because my default state includes mostly avoiding everyone. But by trying on purpose, I seem to have accidentally developed systems which scale better than the innate strengths which many take for granted in themselves.
And I’m writing about trying on purpose, weird though it feels, because several people have recently remarked on the quality of my collaboration. What they perceive as collaborativeness, I experience as a desire to work with my friends, and a recognition that the most effective way to do this is to make friends among my colleagues.
The System
In transitioning to involuntarily remote companies, I noticed a decline in the quality of my work-related social life compared to when I was at in-person or intentionally remote organizations. The intentionally remote culture of Mozilla was built around twice-yearly week-long offsites for the entire organization, which served in part as summer-camp-like friendship accelerators. In-person workspaces offer richer and clearer signaling about social interest: “we’re going to lunch, wanna join us?” grows into invitations to mutually interesting events outside of work as common interests are discovered.
I like working with my friends, and many other people do too. To get more of that, I’ve trial-and-errored my way into a system of making friends at work that’s working well for me so far.
Identify Likeminded Individuals
First, I taught myself to notice when I’ve met someone at work whose company I enjoy. Are meetings more interesting when they weigh in with their perspectives? Do we get to chatting about ordinary topics when we cross paths in larger meetings, and feel disappointed instead of relieved when the conversation returns to the meeting’s actual agenda? Are they interesting to speak with socially when we meet at in-person work events? Is there something about their work, or their approach to work, which I find especially interesting and want to learn more about? Do they express reluctance or regret at ending conversations about topics which interest us both, beyond the mere rote pleasantries?
In short, if we worked in the same office and I saw that they were hanging out in a common area, would their presence make me more likely to go hang out in that area too? These are all ways that my brain tells me someone might be a good candidate to upgrade from acquaintance to friend. Other brains may signal the same potential through a different set of feelings; the trick to this step is discovering what your pattern-match on promising individuals feels like.
If you’re recreating my system for yourself, it would probably be helpful to reflect on other times when you’ve developed friendships with colleagues. What was different about interacting with them, versus interacting with the comparable colleagues who didn’t end up as friends? That’s what you’re looking for.
At this step of the process, being on the same team as me counts as a big enough shared interest to make the system worth trying.
Check Compatibility
To find out how others feel, I rely heavily on the words that they say. Some people are better at picking up subtler cues, but in my experience, even relying on tone of voice can be hit-or-miss.
People can say one thing while meaning another for many reasons, like manners and people-pleasing, and can have wonderful friendships despite that trait! They just don’t tend to have those wonderful friendships with me, because the more we interact socially, the more likely I am to harm them by taking actions which are appropriate based on the content of their speech but inappropriate based on its context.
In the same vein, I like to wait on aggressively pursuing friendship with someone until I’ve seen how they say “no” to optional tasks they don’t want to do. Once I’ve seen them say “no” when a “yes” would have been easier, I know they’re the kind of person who will tell me to back off if I’m being annoying or burdensome.
Those are just my personal compatibility checks. Yours might be similar, or they might be opposite – you might prefer people who will notice subtle changes to your mood without being told, for instance!
Ask the Awkward Question
Once I identify a prospective work friend and verify that their social habits are compatible with mine, I ask them if they’d like to meet more often. This sounds like the most awkward thing ever, but it’s actually not so bad.
The best time to ask if they’d like to meet more often is when we’re already having a good conversation for some other reason. When they are clearly enjoying a conversation with me, it’s unambiguous that they at least sometimes enjoy my company, so it’s a perfect moment to open an invitation to make interactions more frequent.
The question goes something like this: “I wish we did this more often! How would you feel about having a recurring 1:1 chat? Maybe every few weeks?”
The frequency depends on your schedule and how much overlap there is in your work. I have some work friends that I catch up with quarterly, others monthly, others fortnightly.
Set Expectations
I like to set a recurring calendar invite for 1:1s, and be sure that the invitee has “modify event” permissions on it.
My event description usually reads something like, “If we worked in the same office, I would enjoy chatting with you in the kitchen from time to time. But we’re remote, so a call is the next best thing. Please feel free to delete or reschedule this meeting any time it would make your day more difficult.”
I don’t personally use agendas for these meetings. If developing an agenda together is a fun social activity to share with a new friend, though, there’s nothing wrong with that!
Leave a Graceful Exit Open
I don’t like worrying about whether I’m pressuring someone to hang out when they’d prefer not to, so if they cancel several times, I check in about the cadence. “It seems like your schedule has been packed recently; how about I cancel this invite? If you have more time later and want to meet, I’d still be interested!”
For the first few 1:1s with someone, I make sure to have something scheduled to start immediately after the calendar invite’s end time, even if it’s just an alarm on my phone. I know that when I get really into a fun conversation, I can lose track of time and then have a more stressful day as a result. I don’t want to make my friends’ days worse, so as the instigator, I take ownership of ending at the agreed end time as a default.
Some people turn out to tolerate or even prefer these meetings running long, sometimes very long. One work friend who shares my interests in career strategy and loves mentoring will enjoy letting our 30 minutes become 2 hours if we’re both free. Regardless, I consider it polite to check in at the scheduled end time and see when we each need to be someplace else.
In The Meeting
So, you’ve got this person in a call. What do you say?
I personally ask some variant of “how are you doing?” or “how is it going?”. This is their excuse to start talking about whatever is on their mind.
Sometimes people will reflexively respond “good, and you?”. The “and you?” is my invitation to lay out several options for conversation topic, like trying different fishing lures to see what’s of interest today.
To prepare for the meeting, I like to think about 1-2 personal things and 2-3 work things which seem like they might interest the person. Personal things might be “I’ve finally figured out how to get my cat to tolerate existing in the same room as me”, or “I’m looking forward to finally planting tomatoes in my garden”, or “I’m finally getting around to watching such and such a show”. Professional things might be “I’m super heads down in such and such a project”, or “I just found out that this change is coming so now I get to figure out how that impacts my other work”, or similar.
Answering “how are you?” with concise references to 1 personal thing and 1-2 work things gives the person a ton of options. They can request more information on something that they would enjoy hearing about, or offer a related story of their own, or change the topic to something they find more compelling than anything I brought up.
Then again, I don’t hate small talk like some people do. I find that small talk is a challenging game of identifying common interests, almost like wiki-racing. When someone shares information about the weather, it’s a thinly veiled offer to share more about their hobbies and interests: What is it too hot, or too cold, or just right to do? I hold the opinion that small talk is the bootloader for interesting conversation.
Another excellent topic of conversation is to lend and borrow expertise. One of my work friendships is with a product designer, and part of the fun of talking to her is how our areas of greater and lesser expertise line up so compatibly. She answers my “why is it like this?” inquiries, while I answer her “what’s it like to actually use this thing?”, to great mutual benefit.
Afterwards
If you had a nice time, do it again, the next time it shows up on your calendar at a time that works for you both! If you didn’t have a nice time, change plans as necessary so that next time will be better.
If a work friend or even just a friendly collaborator moves on to another opportunity, I like to ask them who else in their part of the organization I should know. Then I can reach out to those people: “such and so told me you’re a good person to know; would you mind a quick call?”. The topic of conversation for that call is pre-established: What you both like about the person who’s leaving, and what mutually beneficial involvements you had with them that you’d like to replace. Replacement is most politely framed as “I’ll really miss how…”, but that’s basically an offer to invite them into your little part of the vacuum left by the departing individual.
I try to remember to intermittently ask the “who else should I know?” question of my work friends, but I rarely remember to. It’s ultimately not essential while someone is still a colleague, but it’s a very important aspect of a good goodbye.
Hi, Future Me
I hope that someday I’ll look back on this post and go “wow, you sure were doing things the difficult and inefficient way!”. If there’s better ways of accomplishing the outcomes of this system that are working for you, please don’t regress to my way of doing things.
But several people in the past few weeks have expressed admiration at the level of connectedness I’ve built within my present workplace, so it seemed worth writing up my current state of the art on the topic.