Connection is Everything: The Case for Intentional In-Person Events

You know when you're stuck on a problem, shooting emails and Slacks back and forth all day, and then — boom — you grab coffee with a coworker and suddenly figure it out in the elevator? That's not magic. It’s not even luck. That's what happens when people talk face-to-face. 

Sidecar Health's CMO Kevin Knight knows that in-person collaboration is key. His simple philosophy: the more intentional you are about your team events, the better their outcomes will be. 

It’s just good business to get the team together, whether they work across the world from each other or across the hall. Either way, any team program you have in mind deserves attention and intention.

But how do you make sure your planning has a real impact on your business?

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Planning the Right Event For Your Team

When Sidecar Health's wanted to get their team together for their SKO, CMO Kevin Knight wasn't just thinking about logistics — he was thinking about ROI. Not the kind you usually think about: the kind that shows up in Slack conversations months later, in how quickly problems get solved, and in whether your best people stick around.

With thoughtful planning and strategic intention, Knight says "you can really change the energy" of staff events. 

These gatherings are incredible opportunities to build connections across the entire workforce. Knight knows you can make them powerhouse moments for both your company's performance and culture.

Here’s the thing. It doesn’t matter if leaders go with a more convenient route — a hotel near headquarters, continental breakfast, conference rooms — or an innovative location. The point is making the event that’s right for your company and goals. 

"If it's been too long since a team got together in person, that team needs to get together in person,” Knight says. “I honestly believe that in those instances, sometimes the agenda actually matters less to the outcome than the mere fact that you got people together in an inspiring location to do something that facilitates organic connection.”

But here's where most companies mess up — they treat these gatherings like one-and-done events. Knight knows better: "You're going to have to continue to invest in in-person interaction, and I think you can get away with doing it less often if you follow culture-building best practices."

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Enter Knight’s Binary: When In-Person Events Matter

In-person gatherings? Mission-critical. But only for specific reasons. 

Here are the two reasons you might want to get everyone together. 

1. You need to lock yourselves in a room with a whiteboard to figure out a problem.
   
   Sometimes, the deep focus — everyone, together, at the same time — is just what you need for a breakthrough.
   
   It helps you get rid of distractions. You’re all there to get work done. And communication is obviously easier than ever (it even keeps going on breaks!).
   
   
2. You want to build company culture. 
   
   Actually free “free time” creates those water-cooler opps that some workers don’t have. And Knight believes you really get to know your coworkers during unstructured time.
   
   Teams don’t always get those mini, unplanned interactions over Zoom or even on different floors of an office building. Some of the best conversations happen while you’re waiting in line for food or walking to a meeting. 
   

Once you've identified the reason for having the event, the next question becomes: how do you maximize the return on that investment? How do you make sure your team event is good for the entire company?

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How Better Getaways = Better Work

Knight says events directly affect attrition — happy, cared-for, and included employees stick around (and you know how expensive and time-consuming it is to replace the ones who don’t). They become champions of the company, promoting it to friends and their networks.

Events are also great for teamwork, even after everyone’s headed home. The creative, collaborative juices are flowing.

“I have been amazed at how much better a remote team is at coming together to solve a problem in the weeks immediately following an in-person gathering," Knight posits.

Fundamentally change your group planning to focus on employee experiences: No matter what’s on the itinerary, prioritizing thoughtful team travel means you’re making a strategic investment in team cohesion, idea-building, and employee retention.

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Take Your Gatherings Sky-High

Knight declares that it’s downright irresponsible to not invest in team meetings. 

“If you want to solve real problems in your business, you have to have real relationships,” Knight says. “You can't expect people who don't have real relationships to have the type of patience, shorthand directness of communication, common sense of purpose and mission if they have not been able to get to know one another at an individual level.”

And don’t forget to take a step back from the business part — think about the people part of it all. 

Those connections make people respond to Slacks with kindness instead of malice; give them opportunities to create and share new ideas; build on familiarity. 

Staff who know, understand, and even like each other(!) work together best, freshly aligned on what your company wants to do most.

Want to see how he brought everyone together? Check out his playbook: How Sidecar Health Transformed Their SKO team gathering experience