1. Connection is still broken — and it’s making everything harder

Brian Elliott set the tone early: engagement is down (again), with Gallup reporting only 31% of employees are engaged. And managers? Just 26%.

That drop in engagement is tied directly to weakened connection. Even for companies mandating return to office, most teams aren’t co-located. So while people are in the office, they’re still not with the people they actually work with.

And without trust, alignment, or clarity, everything else breaks down.

"You told your managers they could hire anywhere. Then you promised quarterly gatherings. Then the CFO cut the budget. And you're wondering why engagement's down?"

2. The best teams treat connection like a product

What do Dropbox and Charlie Health have in common? They both apply product-thinking to their team connection strategy.

At Charlie Health, Geanne Weaver-Hepler rolled out "Team Tuesdays," where regional sales pods created their own names, logos, and hype videos leading up to the national offsite.

"Culture doesn’t just happen. You have to design it. And we learned that connection isn't a nice-to-have — it’s the glue that keeps our growing team aligned, energized, and committed."

Dropbox built a structured matrix to help teams plan intentional gatherings.

"We don’t just plan offsites. We start with: what are you trying to achieve? Trust, clarity, collaboration? That answer should shape the size, format, and who’s even in the room."

3. Peer learning > passive presentations

Charlie Health's sales org has grown from 10 to nearly 400 in under 5 years. In the early days, connection happened naturally. Now, it has to be designed.

Geanne’s biggest learning? The team learns best from each other — not from slides.

They shifted their offsite format to prioritize workshop-style sessions, with heavy emphasis on roleplay and competition. And they introduced random seating to mix experience levels and geographies.

"We used to cram everything in. Now, we protect time for people to learn from each other. That’s what they remember. That’s what sticks."

4. Yes, you can measure impact

One of the top questions from the audience: how do I prove this is worth it?

Geanne shared her approach:

• Run a survey immediately after the event
• Ask the questions leadership cares about (trust, clarity, intent to stay)
• Summarize key themes and quote highlights

"Don’t wait for a pulse survey. Measure the moment while it’s fresh. Then bring it to leadership in their language."

5. Cut the admin. Focus on the experience.

Nick Freeman sees it every day: People teams want to design meaningful gatherings. But they get stuck in spreadsheets, contracts, and hotel phone calls.

"Teams remember the dinners, the off-script conversations, the surprise moments. But planning logistics eats up all your time."

His advice:

• Skip weekends to save money (business travel = cheaper midweek)
• Use AI to optimize travel time, preferences, and group size
• Book in bulk to unlock group discounts (20-30% savings!)

"If you can save time and money, you can finally focus on the part that matters: building the connection your team actually needs."

Thanks for reading. See you next time!

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