How to Plan a Team Outing When Half Your Team is Remote

A product manager I know planned a team bowling night last fall. Great idea, good venue, solid turnout from the office crew. But five of his twelve team members work remotely from three different states. His solution was to set up a Zoom call so the remote folks could "watch and hang out" while the office team bowled.

He told me later that the remote employees lasted about fifteen minutes on the call before quietly dropping off one by one. "It was like watching a party through a window," one of them said.

This is the hybrid team outing problem, and almost everyone gets it wrong the first time.

Why the default approach fails

Most hybrid event planning starts with an in-person activity and then tries to bolt on a remote component. Bowling night plus Zoom. Office happy hour plus a virtual toast. Team lunch plus sending DoorDash gift cards to remote employees.

The intention is good. The execution makes remote team members feel like an afterthought, because they are. The event was designed for people in the room. The virtual addition was an accommodation, not an equal experience.

I've surveyed remote employees about hybrid team events, and the feedback is consistent. They'd rather be excluded entirely than included as spectators. Being on a screen while your coworkers are physically together, laughing, having side conversations you can't hear, is actually worse for morale than not being invited.

Two approaches that actually work

Approach one: fly people in. If your budget allows it, the highest-impact thing you can do is bring remote team members to one location for team events. Not every month. But quarterly, or even twice a year, a focused in-person gathering where everyone is physically present eliminates the hybrid problem entirely.

A 40-person SaaS company I advise flies their remote employees (about 15 people) to their Denver office twice a year for a three-day team week. The cost is significant. Flights, hotels, meals. But their retention numbers for remote employees are dramatically better than industry averages, and they attribute much of that to these gatherings.

The key is making the trip worthwhile. Don't fly people in for a day of meetings. Plan real social time. Dinners, activities, unstructured hangout time. The meetings can happen on Zoom anytime. The in-person experience is irreplaceable.

Approach two: design for the lowest common denominator. If bringing people together isn't feasible, plan activities that work equally well regardless of location. This usually means the activity happens individually or in small virtual groups, with the shared element being timing and a common experience.

Examples that work surprisingly well. Cooking classes where a chef leads everyone through the same recipe on video (everyone gets ingredients shipped in advance). City exploration challenges where teams complete location-based tasks in their own cities simultaneously. Book club style discussions where everyone reads or watches something and then discusses it in small breakout groups.

The common thread is that nobody's experience is secondary. Everyone is doing the same thing, just in different places.

The logistics of hybrid planning

If you do plan an event with both in-person and remote components, a few tactical things make a massive difference.

Invest in audio quality at the in-person venue. The number one complaint from remote attendees at hybrid events is that they can't hear what's happening. A single laptop microphone in a noisy restaurant is useless. Get a proper conference microphone or, better yet, have a designated person whose job is to be the remote team's connection point.

The best hybrid event I attended was when they gave one in-person person a phone and told them to just FaceTime me for the evening. It was like having a buddy there. Way better than being on a big screen nobody looked at.

Create small-group moments. If you have 20 people in a room and 8 on video, don't try to have one big group conversation. Break into groups of 4-5 where each group has at least one remote person. The intimacy of a small group call is infinitely better than being one of eight faces on a screen that a room full of people occasionally glances at.

Send the same food. If the in-person team is having pizza, ship pizza to your remote team. Same restaurant if possible, or the local equivalent. This sounds silly, but eating the same meal at the same time creates a surprisingly strong sense of shared experience.

When to just do separate events

Sometimes the best hybrid strategy is admitting that certain activities don't translate across a screen. Instead of forcing a subpar hybrid experience, plan separate events optimized for each group.

In-person team gets their bowling night. Remote team gets a virtual game night that same week, with a proper budget for food delivery and activities designed for video. Both groups get a great experience. Neither group is an afterthought.

This does mean more planning work. But two good events beat one mediocre hybrid event every time.

Your remote team members chose remote work, but they didn't choose to be disconnected from their coworkers. The extra effort to plan events that genuinely include them pays back in loyalty, engagement, and the kind of trust that makes distributed teams actually function.