Somewhere around 2020, every remote team decided they needed a “culture initiative.” The playbook became predictable: virtual happy hours on Friday, a Donut bot randomly pairing people for coffee chats, a trivia game every other week, and a Slack channel called #watercooler where someone posts a conversation prompt that gets three awkward replies before going silent.
Most of these don’t work. Not because they’re bad ideas, exactly, but because they misidentify the problem. The question isn’t “how do we replicate office socializing over video?” The question is “what actually creates connection between people who work together remotely?”
The answer, in our experience, is simpler and less fun to put in a company newsletter: shared work, done well, with space for humans to be human.
Why the standard playbook fails
Virtual happy hours
The pitch: “It’s like grabbing drinks after work, but on Zoom!” The reality: eight people on a grid, two of whom are doing most of the talking, three who clearly have their camera on but are doing something else, and everyone counting the minutes until they can leave without seeming antisocial.
Virtual happy hours fail because they try to manufacture spontaneity. In-person socializing works because it’s low-stakes and opt-in: you bump into someone in the kitchen, you walk to lunch together, you overhear a conversation and join in. None of this translates to a scheduled video call where everyone is performing “casual” for an audience.
The deeper problem: mandatory fun creates resentment. The people who most need connection (introverts, people in isolated time zones, new hires) are the ones who find these events most draining. And the people who enjoy them are usually the ones who already have strong social connections on the team.
Donut bot and random pairings
Donut and similar tools randomly pair team members for one-on-one virtual coffee chats. The concept is sound — serendipitous conversations are valuable, and remote teams don’t get them naturally.
In practice, the conversations often stall. Two people who don’t work together directly are matched, they schedule a 15-minute call, and they struggle to find common ground beyond “so, how’s your week going?” After three rounds of this, participation drops to the same five people.
The fix isn’t to abandon random pairing — it’s to give people something to talk about. More on this below.
The #watercooler channel
A Slack channel meant for casual, non-work conversation. Someone posts “What’s everyone watching?” or “Hot take: best pizza topping?” These generate a burst of replies on day one and crickets by week three.
Watercooler channels fail because they’re extracting social interaction from its natural context. In an office, you chat about TV shows while waiting for the coffee machine — it happens in the gaps between work. On Slack, it’s a separate destination you have to consciously visit, which makes it feel like another thing on the to-do list.
What actually builds connection
After trying (and mostly abandoning) the standard remote culture playbook, here’s what we’ve found works. None of it is flashy. All of it is grounded in how people actually bond.
1. Working together builds relationships
The strongest relationships on our team are between people who’ve collaborated closely on a project. Not because we paired them for a coffee chat, but because they spent three weeks solving a hard problem together and built mutual respect through the work.
This isn’t accidental — it’s something you can design for. When assigning project teams, consider relationship-building as a factor. Pair a new hire with a senior person who’s good at including others. Put two people from different functions on a cross-functional project. Rotate who leads the weekly sync so everyone gets reps facilitating.
The practical implication: if you want better team culture, invest in better collaboration processes — clearer briefs, better async communication, more thoughtful project assignment — rather than more social events.
2. Small, consistent rituals beat big events
We have a few rituals that have survived for over a year. They work because they’re small, low-pressure, and woven into the work rhythm:
Friday wins. A Slack thread in #social-general every Friday where people post one thing from the week — work or personal — that they’re pleased about. Recent examples from our team: “Shipped the new onboarding flow — first hire starts Monday,” “Finally fixed that flaky CI test that’s been failing for weeks,” “Took Wednesday off and actually didn’t check Slack once.” It takes 30 seconds to write and 2 minutes to read everyone else’s. No video call. No pressure to be entertaining. Just a regular touchpoint.
Pairing sessions. Once a week, two people work on a shared task for 45-60 minutes on a video call — optional, self-scheduled. This is actual work — pair programming, collaborative writing, design review — with cameras on. The social connection is a byproduct of the shared activity, not the goal. These have been more valuable for relationships than any happy hour we’ve tried.
Onboarding buddy system. Every new hire gets a buddy for their first 30 days (detailed in our onboarding guide). This creates at least one solid relationship from day one and gives the new person a safe person to ask “dumb” questions.
Personal check-ins in 1:1s. Our 1:1 template starts with “How are you, genuinely?” before getting to work topics. This is a two-minute question, not a therapy session, but it creates a regular moment where people acknowledge each other as humans. Managers who skip this lose signal on how their reports are actually doing.
3. Make Donut work with structure
We didn’t abandon Donut — we made it work better. The change: each Donut pairing gets a prompt that gives them something concrete to discuss.
Examples:
- “Share one workflow hack that’s saved you time recently”
- “What’s a tool or technique you learned at a previous job that you think we should try here?”
- “What’s one thing about your work setup that you’d recommend?”
These prompts work because they’re specific and work-adjacent — they give people a way in without requiring them to manufacture small talk. Participation went from ~40% to ~75% after we added prompts.
The other change: we set Donut to pair people biweekly, not weekly. Weekly pairings felt like an obligation. Biweekly gives people time to actually schedule and have the conversation without it feeling like a burden.
4. Shared context through written culture
This is the least obvious one, but it might be the most important. Teams that write things down — decisions, rationale, context, process — build a shared understanding that bonds people to the work and to each other.
When you read a teammate’s well-written project brief, you learn how they think. When you see their decision log and understand why they made a tough call, you build respect. When your Notion wiki is rich and navigable, new hires feel included from day one because the team’s knowledge is accessible, not locked in people’s heads.
Written culture also reduces the power dynamics that undermine connection. In a meeting, the loudest voice wins. In an async discussion, everyone has equal space to think and respond. People in later time zones don’t miss the decision. Introverts can contribute without interrupting. GitLab’s handbook on informal communication is worth reading here — they’ve documented how a 2,000+ person fully-remote company builds connection, and their conclusion is similar: structure matters more than spontaneity.
5. Physical meetups when possible
This is the expensive one, and we include it because it works disproportionately well. One in-person meetup per year — even a short one, 2-3 days — creates more lasting connection than six months of virtual events.
The key: don’t fill the meetup with meetings. Leave unstructured time. Eat meals together. Work in the same room for a few hours. The value of being physically present comes from the informal interactions, not from sitting in a conference room together.
If budget doesn’t allow for a full team meetup, regional sub-groups meeting up locally still helps. Two people on the team who live in the same city having lunch once a quarter is valuable.
What to stop doing
If your team is currently running culture initiatives that feel forced, here’s what we’d suggest:
Stop: Weekly virtual happy hours, mandatory fun events, conversation-prompt channels that nobody uses.
Keep but fix: Random pairings (add prompts and reduce frequency), social Slack channels (post less, make them opt-in, don’t worry about engagement metrics).
Start: Pairing sessions around real work, structured new-hire buddies, personal check-ins in 1:1s, Friday wins thread, better collaboration design.
Accept: Remote teams will never have the same social dynamics as co-located teams. That’s okay. The goal isn’t to replicate the office — it’s to build genuine connection within the constraints of distributed work. That connection comes from working well together, not from icebreakers.
The best remote culture isn’t a program or an initiative. It’s the byproduct of a team that communicates clearly, collaborates effectively, and makes space for people to be themselves. Basecamp’s guide to remote work makes a similar argument from a different angle — culture isn’t something you bolt on, it’s how you work. Build the systems that enable good work, and the culture follows.